Cross v. Perez

Filing 15

MEMORANDUM DECISION AND ORDER, I hold that the state court unreasonably applied Strickland v. Washington, 466 U.S. 668, 104 S.Ct. 2052 (1984), and therefore grant the writ of habeas corpus. The writ of habeas corpus is granted to the extent that peti tioner's guilty plea is vacated, unless respondent consents to the imposition of an eight-year sentence, together with any other conditions attendant to the sentence previously imposed, within 120 days. (Ordered by Judge Brian M. Cogan on 10/3/2011) c/m by chambers. Fwd. for Judgment. (Galeano, Sonia)

FILED

U$ DISTRICT COURT F D N.Y.

UNITED STATES DISTRICT COURT
EASTERN DISTRICT OF NEW YORK
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OCT 04 2011 r,6;\ · ~

IN CLERK'S OFFICE

V
BROOKLYN OFFISE

KYLE CROSS,
Petitioner,

MEMORANDUM
DECISION AND ORDER

-against-

II Civ. 1186 (BMC)
ADA PEREZ, WARDEN OF DOWNSTATE
CORRECTIONAL FACILITY,
Defendant.
X

COGAN, District Judge.
Petitioner prose seeks a writ of habeas corpus pursuant to 28 U.S.C. § 2254(d) in

connection with his guilty plea to a charge of armed robbery. Petitioner claims that he accepted
a plea offer based on his attorney's incorrect advice as to whether a prior New Jersey conviction
qualified him as a second violent felony offender under New York law. This case raises issues
as to whether a waiver of appellate and collateral-challenge rights in connection with a guilty
plea is worth the paper it is written on; the differences between federal and New York law in
applying that waiver; and the extent to which an objectively reasonable defense lawyer should
understand these issues when advising a client of how foreign convictions will affect his
sentence. I hold that the state court unreasonably applied Strickland v. Washington, 466 U.S.

668, 104 S.Ct. 2052 (1984), and therefore grant the writ of habeas corpus.
I

The facts set forth below are taken from the record of proceedings in the state courts. In
addition, the Court has accepted as true petitioner's factual allegations concerning his off-the-

record discussions with his defense counsel at the time of his guilty plea and sentence, as they
are detailed and credible, and respondent has not sought to contradict them.
Petitioner, facing a charge of first-degree robbery, decided to conditionally accept a plea
agreement that the prosecutor offered on the eve of trial. The discussions over whether petitioner
would accept it, some of which occurred off the record, initially focused on whether he would be
sentenced as a "persistent violent felony offender" under§ 70.08(1)(a) of New York's Penal
Law, which carries a mandatory minimum sentence oftwenty years' custody. This enhanced
sentencing status depended upon how many, if any, of three prior New Jersey convictions would
"count" as predicate violent felony offenses under the Penal Law. When that issue was
identified during on-the-record plea negotiations, the prosecutor agreed to allow a plea to a lesser
charge that would carry a term of twelve years to life. The trial court was scrupulous in laying
out petitioner's options without pressuring him to accept the twelve-year plea.
At that point, the transcript reflects that the parties had an off-the-record discussion.
Petitioner asserts, and it is consistent with what follows in the transcript, that he had done his
own legal and factual research, obtaining the indictments underlying his New Jersey convictions
and comparing these convictions to their New York statutory counterparts. Petitioner presented
supporting authorities to his attorney and communicated his view that none of his three prior
New Jersey convictions were sufficiently analogous to their New York statutory counterparts to
serve as predicate violent felony offenses. According to petitioner, his attorney, the prosecutor,
and the trial court agreed with him that two of his prior convictions corresponded to New York
misdemeanors and petitioner therefore could not be sentenced as a persistent violent felony
offender (a status that could only be imposed if petitioner had two or more prior violent
felonies). However, the prosecutor, defense attorney, and judge each held the view that

2

petitioner's third prior conviction, for aggravated assault against a police officer under N.J. Stat.
1

§ 2C:12-l(b)(5)(a) (the "New Jersey assault statute"), qualified as a predicate violent felony
under N.Y. Pen. L. § 70.04(1)(b)(i), which provides for enhanced sentencing of a "second violent
felony offender" (as opposed to a "persistent violent felony offender"). Under the attorneys' and
the court's view, the New Jersey assault conviction qualified as a predicate felony because it is
analogous toN. Y. Pen. L. § 120.11, "Aggravated Assault on a Police Officer or Peace Officer"
(the "New York assault statute"). 2 Petitioner disagreed with his attorney, the prosecutor, and the
trial court, but deferred to their view of the issue. Based on the determination that petitioner was
a "second violent felony offender," rather than a "persistent violent felony offender," the
prosecutor lowered his plea offer to ten years, which petitioner accepted. This sentence reflected
the minimum sentence for a second violent felony offender convicted of first-degree robbery in
New York.
The trial court then went back on the record and stated that petitioner had agreed to plead
guilty as a second violent felony offender and accept a ten-year sentence, summarizing their offthe-record discussion as follows:
THE COURT: On the record. Let me start. Everybody sit for a second. We have
been discussing this case at length off the record to see, number one, whether or
not defendant is truly a mandatory violent persistent felony offender, at least
facing adjudication as such, upon a conviction on the matter before me today.

1

The statute provides that it shall be an aggravated assault in the third degree when a person assaults "any law
enforcement officer in the perfonnance of his duties while in unifonn or exhibiting evidence of his authority or
because of his status of a law enforcement officer ... if the victim suffers bodily injury." Under N.J. Stat. § 2C: JJ.
l(a), '"[b]odily injury' means physical pain, illness or any impainnent of physical condition."
2 "A

person is guilty of aggravated assault upon a police officer or a peace officer when, with the intent to
cause serious physical injury to a person whom he knows or reasonably should know to be a police officer
or peace officer engaged in the course of performing his official duties, he causes such injury by means of a
deadly weapon or dangerous instrument." Under N.Y. Pen. L. § 10.00(10), '"[s]erious physical injury'
means physical injury which creates a substantial risk of death, or which causes death or serious and
protracted disfigurement, protracted impainnent of health or protracted loss or impairment of the function
of any bodily organ."

3

It would appear that there is a very good reason to believe that he is not. Upon
defendant'~ own research and the paperwork which we are going to be
photocopymg and [the prosecutor] will take back to his office so that at the time
of sentencing, defendant can be dealt with as a second violent felony offender but
not a mandatory persistent violent felony offender. That sounds okay right now.
[DEFENSE COUNSEL]: Yes.
[THE PROSECUTOR]: Yes, Judge.
THE COURT: Right. And People, from your analysis of what you're being
shown and going over the statute and our penal law sections as opposed to the
New Jersey statute, it would appear that defendant's research seems accurate,
actually.
(THE PROSECUTOR]: It appears that the certified documents in comparison
with the New Jersey statutes of aggravated assault and other related New Jersey
statutes that appears to be accurate, Judge.
THE COURT: Right, good. And then based on that, I understand now that you
have approval at this time, therefore (we are] going to do this right now which is
what I'm ready to do, to offer defendant as a second violent felony offender
which- he will be adjudicated formally as such prior to sentence, but to offer him
a sentence, a determinate sentence of ten years flat.
[THE PROSECUTOR]: Correct.
The trial court then accepted petitioner's guilty plea after putting him through a very
thorough allocution as to the fact of his guilt and the rights that he was surrendering by pleading
guilty. The trial court specifically advised petitioner that he would be sentenced as a second
violent felony offender and receive ten years:
THE COURT: ... The promised sentence often years is based on the fact that it
is this Court's understanding that prior to sentence you are admitting that you
have what constitutes a previous violent felony conviction, which based on that,
will therefore expose you to sentencing as a second violent felony offender.
We are going to arraign you on all the appropriate paperwork and adjudicate you
as such prior to sentence on the next Court date. Do you understand, sir?
THE DEFENDANT: Yes.
THE COURT: But without- Putting the formalities aside, is it your intention and
your understanding that you're going to be prepared to admit such prior to
sentence?
THE DEFENDANT: Yes.

4

THE COURT: Okay. And indeed this whole plea is predicated on that
Otherwise, you know .
THE DEFENDANT: Understood.
[DEFENSE COUNSEL]: So the record is complete, the other side of the coin is
that o~ the date of sentence, the understanding is that [the prosecutor] will not
come In here and say I have done more research and that one conviction in Jersey
that I agreed isn't or I did agree was a non-violent now I'm changing my mind.
[THE PROSECUTOR]: That's [my] understanding.
THE COURT: You don't intend to do that?
[TilE PROSECUTOR]: No.

The trial court also went over the appeal waiver that was part of the plea agreement. In
reference to the written appeal waiver that petitioner signed, the trial court advised him:
THE COURT: ... All right, Mr. Cross, let's discuss this issue of waiver of right
to appeal.
You, sir, as well as every defendant would have, without signing this document,
you would have every right to challenge this plea and sentence at a later time.
So if couple of days from now, a hundred days from now or a thousand days from
now, just to give you some examples, you decide that you want to challenge this
plea and sentence before me or another Judge in this Court or in a higher Court or
even in Federal Court, you would have every right to make such challenges. You
understand?
THE DEFENDANT: Yes.
THE COURT: And or file such appeals. You would have that right. But by
agreeing to this waiver document, you're saying, Judge, I understand that I would
have had those rights but I am knowingly, intelligently and voluntarily giving up
my right to make such challenges and/or challenge such appeals, do you
understand?
THE DEFENDANT: Yes.
THE COURT: And why would you do that? Well, you certainly can recognize
from what just took place today before we even got to the point of putting on a
negotiated disposition on the record, that it's the D.A. 's position that they are
offering you a plea bargain, they want this to be final. Took a lot of work to work
out this disposition. They don't want you to then turn around and try to challenge
or undo this plea and sentence at a later time. You understand?
TilE DEFENDANT: Yes.
THE COURT: And you're saying, sir, you're saying, Judge, yes, I understand this
and I'm willing to give up those legal and constitutional rights that I otherwise

5

would have as part of what we call the consideration, part of what you are giving
up as part of the plea bargain in this case, okay.
That is a primary reason why the D.A. is offering you this plea bargain with a
reduced sentence, okay. And you are saying, Judge, I understand this and I'm
happy to have this negotiated plea, I understand I am giving up my right to
challenge it. You understand?
THE DEFENDANT: Yes.
The written waiver, signed by petitioner, stated, in part, as follows:
1. Waiver of Right to Appeal: I acknowledge that I have been advised
of, and waive, my right to appeal from the judgment of conviction or sentence ....
This waiver applies to all issues that may validly be waived. This includes
but is not limited to any issue regarding the effectiveness of counsel prior to my
plea in this case and any issue that may arise with respect to the imposition of
sentence. I also waive any issue that may arise with regard to my adjudication as
a second felony offender, second violent felony offender ... or persistent violent
felony offender.
2. Waiver of Right to File Post-Trial Motions and Applications: I have
been advised of, and waive, my right to file motions to vacate my conviction and
to set aside my sentence under C.P.L. Article 440, my right to file habeas corpus
petitions in state and federal court, and any right I may have to file any other
motion or application attacking my conviction in state or federal court.
Approximately one month later, the trial court sentenced petitioner as a second violent
felony offender to ten years as per the agreement. Petitioner expressly waived his right to
contest the predicate felony conviction. Consistent with the appeal waiver, petitioner did not
take a direct appeal from his conviction and sentence.
However,just over two months after his sentence, petitioner filed a motion under N.Y.
C.P.L. § 440.10 to set it aside or reduce it. He argued, inter alia, that his counsel was ineffective
in advising him that the New Jersey aggravated assault conviction made him a second violent
felony offender. Petitioner asserted that, had his counsel properly argued to the trial court that
the New Jersey conviction could not serve as a predicate offense, he would not have been
deemed a second violent felony offender. He further asserted that this would have caused him to

6

receive, and accept, a plea agreement offering eight years instead often years, the minimum for a
first time violent offender with a prior felony conviction. 3 Petitioner sought a sentence reduction
to bring him to that level. The § 440 court, by the same judge who sentenced petitioner, found
that petitioner had "executed this waiver in a knowing, voluntary, and intelligent fashion,
particularly giving up the right to attack what he is challenging herein. The defendant is no
novice to the criminal justice system with many prior convictions." Additionally, the§ 440 court
rejected the ineffective assistance claim on the merits, noting that petitioner had a "full"
discussion of his New Jersey convictions with his attorney prior to entering the plea, and had
reviewed his own research with his lawyer prior to accepting the prosecutor's offer. The
Appellate Division denied leave to appeal.
II

Respondent first contends that, even without regard to the decision of the§ 440 court,
petitioner's execution of a waiver agreement as to his federal habeas corpus rights (combined
with his allocution acknowledging that waiver) bars federal habeas corpus review. This
contention subsumes two issues: (a) will a federal court recognize a waiver of federal habeas
corpus rights, entered into in state court, as an independent ground under federal law upon which
to deny review; and (b) will a claim of ineffective assistance of counsel as to entry into a plea
agreement under these circumstances vitiate the waiver?

3 Petitioner appears to be referring to N.Y. Pen. L. § 70.06(6)(a), which provides an eight-year minimum sentence
for a first-time violent felon with a prior, non-violent felony conviction. Respondent does not refute petitioner's
assertion that eight years would have been the applicable minimum sentence, had petitioner not been deemed a
second violent felony offender.

7

A.
There is surprisingly little authority as to the first issue, and none from the Second
Circuit. It could be argued that, since§ 2254 does not refer to the possibility of waiver, and
since the federal court's charge under the statute is to review merits-based state court decisions
or deny review based on recognized state procedural grounds, there is no vehicle for enforcing a
state court waiver of federal habeas corpus relief in federal court. However, I think the better
view is to analogize such waivers to those arising from federal convictions in which review is
sought under § 2255, and to recognize § 2254 waivers under the same circumstances.
This is the conclusion Judge Bianco recently reached in Rodriguez v. Conway, No. 066358,2010 WL 92911 (E.D.N.Y. Jan 6, 2010). He held that such a waiver would be given
effect in federal court if it meets the recognized federal standard of being knowing and voluntary.
Because the written waiver in that case explicitly covered federal habeas corpus relief, Judge
Bianco rejected the petitioner's contention that he thought he was only surrendering his state
court appellate rights. He rejected this contention even though- unlike here- the state court's
oral explanation of the waiver did not expressly refer to federal rights. Judge Bianco
distinguished the Eleventh Circuit's decision in Allen v. Thomas, 161 F .3d 667 (11th Cir. 1998),
which refused to find a waiver of the right to seek federal habeas corpus relief, because the
waiver at issue there did not expressly refer to federal habeas corpus proceedings. Compare
Brown v. Thompson, No. 06-126,2007 WL 2594054, at *I (M.D. Ga. Sept. 5, 2007)
(recognizing waiver in§ 2254(d) case where the waiver expressly referred to federal habeas
corpus rights).
It is well established that a federal defendant may waive both his right to direct appeal

and his§ 2255 rights. See Garcia-Santos v. United States, 273 F.3d 506, 508 (2d Cir. 2001).
8

The waiver of federal habeas review by a state defendant under§ 2254(d) is one step removed
from these waivers, as it provides an even narrower standard of review than direct appeal or§
2255 review. In that sense, at least, the right being surrendered is less fundamental than the right
to de novo review in the context of a direct appeal or a§ 2255 petition. And although§ 2254
does not expressly refer to a waiver of the rights that it grants, neither does § 2255, and yet the
federal courts regularly recognize § 2255 waivers. See id. Most federal rights are subject to
waiver if the waiver is knowingly and intelligently given, see Johnson v. Zerbst, 304 U.S. 458,
463-64,58 S.Ct. 1019 (1938), and the right to federal habeas corpus review of a state court
conviction should be treated the same way.
Putting aside for the moment petitioner's claim of ineffective assistance of counsel,
which is discussed below, there can be no question on this record that he knowingly and
voluntarily waived his right to collaterally attack his sentence and specifically his right to federal
habeas corpus review. See generally Parke v. Raley, 506 U.S. 20, 28-29, 113 S.Ct. 517 (1992)
("The standard was and remains whether the plea represents a voluntary and intelligent choice
among the alternative courses of action open to the defendant.") (internal quotation marks
omitted). He was an active participant in the plea discussions and had material input in
structuring the plea agreement based upon his own legal research and analysis. He was advised
of and acknowledged the waiver twice: when the state court explained it to him, and again in a
detailed but clear, stand-alone written document that constituted the waiver. He understood
completely that one, and only one, of his three New Jersey convictions would "count" in
determining his sentencing status, and he understood that this was part of the quid pro quo for his
plea. He does not claim that he had a failure of understanding with regard to the waiver. Indeed,

9

petitioner himself describes his decision as knowing and voluntary. Writing in the third person,
petitioner stated:
The petitioner was obviously aware of the evidence against him, and the fact that
he emphasized his willingness to plea early in the proceedings, but more
importantly, being cognizant of the people, counsel and the court being convinced
that the New Jersey conviction was a [qualifying] violent felony, the petitioner
knowingly, voluntarily and intelligently accepted the plea often years, the very
minimum for a second violent offender, and was sentenced accordingly.

B.
Having determined that petitioner knowingly and voluntarily executed a waiver of his
federal habeas rights, the next question is whether the waiver bars the instant petition.
The petitioner in Garcia-Santos, in his§ 2255 application, claimed that his attorney was
ineffective for "fail[ing] to inform him of the adverse consequences he faced if he signed the plea
agreement." 273 F .3d at 508. The Second Circuit did not reach the merits of the claim, finding,
instead, that the appeal waiver 4 in the plea agreement expressly barred habeas corpus relief. The
Circuit affirmed the district court's finding that the waiver itself was voluntarily and knowingly
given based on the circumstantial evidence surrounding the guilty plea:
The conclusion was supported by the following facts: (1) petitioner signed the
plea agreement, (2) he stated to the magistrate judge that he had read and
understood the plea agreement, (3) Garcia-Santos did not attempt to appeal his
sentence, even though he had been told by the sentencing judge that he had the
right to appeal, (4) he did not claim, in his § 225 5 motion, that he had not
understood the waiver contained in his plea agreement, and (5) even in his
petition for reconsideration, he did not assert explicitly or under oath that at the
time of his plea he did not understand that he was giving up his right to appeal
and petition under§ 2255.
ld. Significantly, the Circuit reached this conclusion even though the district court had not
mentioned or discussed the appeal waiver when accepting Garcia-Santos's guilty plea.
4

I use the tenn "appeal waiver" as a shorthand reference that includes a waiver of both direct appeal and collateral
proceedings, except where specifically noted otherwise.

10

Garcia-Santos could be read as allowing a petitioner to use an ineffective assistance claim
to attack a plea agreement only if the ineffectiveness claim homes in on the waiver itself, rather
than the advice given regarding whether to accept the plea agreement. There are reasons,
however, not to read Garcia-Santos so broadly. First, in holding that an appeal waiver could
preclude a§ 2255 petition, the Court cited with approval the Tenth Circuit's decision in United
States v. Cockerham, 237 F.3d 1179 (lOth Cir. 2001). There, the rather vague claim on habeas
review was that the petitioner's counsel had mistakenly counseled him to take the offered plea
when the Government allegedly could not have offered sufficient evidence to sustain his
conviction at trial. Although the Tenth Circuit held that rights under§ 2255 could be waived, its
ultimate conclusion was that
a plea agreement waiver of postconviction rights does not waive the right to bring
a§ 2255 petition based on ineffective assistance of counsel claims challenging the
validity ofthe plea or the waiver. Collateral attacks based on ineffective
assistance of counsel claims that are characterized as falling outside that category
are waivable.
Cockerham, 237 F.3d at 1187 (emphasis added) 5
Garcia-Santos also cited with approval other circuits' decisions that are in line with
Cockerham. See DeRoo v. United States, 223 F.3d 919, 924 (8th Cir. 2000) ("A defendant's
plea agreement waiver of the right to seek section 2255 post-conviction relief does not waive
defendant's right to argue, pursuant to that section, that the decision to enter into the plea was not
knowing and voluntary."); Jones v. United States, 167 F.3d 1142 (7th Cir. 1999) (holding that
waiver does not generally preclude § 2255 relief in the face of claims of ineffective assistance in

sIn the Tenth Circuit, these kinds of claims have become known as "Cockerham claims." See United States v.
Akers, 377 F.App'x 834, 836 (lOth CiL 2010).

II

negotiating the plea agreement, but finding that allegations of ineffective assistance too
conclusory to overcome waiver).
There is tension between Garda-Santos and some of the cases, like Cockerham, that it
cites with approval. Where Garcia-Santos seemed to distinguish claims attacking the waiver
specifically from claims attacking the plea agreement generally, Cockerham suggested that a
petitioner's decision to waive his appellate or collateral-attack rights, in the context of a plea
agreement, is not severable from his decision to accept the plea offer.
However, the Second Circuit subsequently decided three cases in which the Court's
reasoning was more in line with Cockerham than with Garda-Santos. In United States v.
Hernandez, 242 F.3d 110 (2d Cir. 2001), on direct appeal of a denial to vacate a guilty plea, the
defendant claimed his attorney misled him as to the consequences of his plea. Specifically, the
defendant claimed that he did not speak English and had only five minutes to review the
agreement through an interpreter before entering the courtroom, and that his attorney told him he
would only be sentenced to two years in prison and did not explain that he was waiving his
appellate rights. The Second Circuit declined to enforce the appeal waiver, noting, albeit in
dictum, that
a plea agreement containing a waiver of the right to appeal is not enforceable
where the defendant claims that the plea agreement was entered into without
effective assistance of counsel. The rationale is that the very product of the
alleged ineffectiveness cannot fairly be used to bar a claim of ineffective
assistance of counsel.
Of course, the refusal to apply such a waiver provision in these circumstances
only allows appellate review of the constitutionality of the process by which the
plea agreement was consummated.

12

Hernandez, 242 F .3d at 114-15 (citations and quotations omitted). Nevertheless, the Court
affirmed the conviction because the defendant's statements during his allocution were directly
contrary to the allegations in his motion to vacate his plea.
In Frederick v. Warden, Lewisburg Corr. Facility, 308 F.3d 192 (2d Cir. 2002), the Court
held that a claim that counsel was ineffective for failing to object to the inadequacy of the trial
court's compliance with Fed. R. Civ. P. 11 during the plea allocution could be raised in a § 2255
petition, notwithstanding a waiver in the plea agreement ofthe right to collaterally challenge the
sentence. The Court explained that "a waiver of appellate or collateral attack rights does not
foreclose an attack on the validity of the process by which the waiver has been procured, here,
the plea agreement." Frederick, 308 F.3d at 195.
The question thus becomes the breadth of the definition of "process" by which either the
waiver or the agreement itself was procured. The Second Circuit's most recent decision on
appeal waivers in collateral review cases, Parisi v. United States, 529 F.3d 134 (2d Cir. 2008),
defines it expansively. There, the petitioner claimed that his guilty plea should be vacated and
the indictment dismissed because his counsel was ineffective for failing to seek dismissal under
the Speedy Trial Act. See Zedner v. United States, 547 U.S. 489, 126 S.Ct. 1976 (2006). The
Court explained that the petitioner's appeal waiver, which was part of his plea agreement, barred
his claim. But the Court cited Hernandez for the proposition that a challenge to the
"constitutionality ofthe process by which he waived his right to appeal" would survive the
waiver. Parisi, 529 F.3d at 138 (emphasis in original).
The Parisi Court then discussed the scope of the word "process" in the context of a
waiver procured through a plea agreement. The Court explained that the petitioner was wrong to
assume that"[eJverything that occurs prior to a guilty plea" is part of the "process" simply
13

because it ultimately affects the petitioner's bargaining position during plea negotiations. Id.
The petitioner had therefore waived his right to claim that his counsel was ineffective for failing
to move for dismissal on speedy trial grounds prior to the plea agreement process. Instead, the
Court held that Parisi's Sixth-Amendment claim could survive his waiver if there was a
connection between "the alleged ineffectiveness of Parisi's counsel" and "the voluntary nature of
his plea." In finding that Parisi had established this connection, the Court drew a very fine
distinction: it inferred, based solely on Parisi's prose status, that he was additionally arguing
that "his attorney was ineffective in advising him to accept the plea agreement rather than
advising him to move to dismiss the indictment with prejudice based on alleged Speedy Trial Act
violations." 529 F.3d at 139. Because this claim challenged the lawyer's advice during the plea
agreement "process," the Court found that the ineffectiveness was sufficiently connected to the
voluntariness of Parisi's plea and the claim therefore survived Parisi's waiver.
Parisi's broad "connectivity" standard, in my view, allows virtually all ineffective
assistance claims to survive waivers procured through plea agreements. It is hard to imagine a
material and erroneous act by counsel, committed prior to the guilty plea, which would not infect
the decision as to whether or not to enter into the plea agreement. If a Court can simply infer, as
the Parisi Court did, that a petitioner's ineffective assistance claims challenge his counsel's
ultimate advice as to whether or not to take a plea, the waiver will drop out of almost any case in
which an ineffective assistance claim is raised, and the habeas court may as well proceed directly
to the Strickland claim with little more than a passing glance at the waiver.
Applying Parisi, as I read it, I find that petitioner's waiver may not serve as a federal
procedural bar to his claims of ineffective assistance of counsel. There is no need to infer
"connectivity" from petitioner's allegations- he expressly alleges that, had his attorney done his

14

job and discovered that the final New Jersey conviction could not serve as a predicate conviction,
petitioner would have been offered, and would have accepted, a more lenient plea agreement.
Indeed, the attorney error alleged here is much closer both temporally and causally to the issue of
whether the plea was voluntary because, unlike in Parisi, the erroneous legal analysis and advice
was itself the driving force behind the structuring of the plea agreement. It is manifest, from the
transcript of petitioner's plea allocation, that his decision to plead guilty (and therefore, his
decision to waive his habeas rights) was directly premised on his counsel's faulty advice
regarding his New Jersey assault conviction.
Virtually all of the Second Circuit cases reject a waiver where the defendant attacks the
"process." There is no more fundamental aspect of the plea agreement process than effective
advice from counsel with regard to how the sentence will be computed under the proposed plea.
See Boria v. Keane, 99 F.3d 492 (2d Cir. 1996). Petitioner's waiver, standing alone, therefore
does not preclude my review of his Sixth Amendment claim.

III
According to respondent, even if petitioner's waiver is ineffective to bar federal habeas
relief, the§ 440 court's decision recognizing the waiver is an independent and adequate state law
ground for its decision which precludes federal review of petitioner's ineffective assistance
claim. For reasons similar to those described above for rejecting the concept of a federal
procedural bar in this case, I reject the adequacy of the§ 440 court's state procedural bar.
A petitioner's federal claims may be procedurally barred from habeas corpus review if
the state court invoked "independent and adequate" state procedural grounds. Coleman v.
Thompson, 501 U.S. 722, 729-33, 111 S.Ct. 2546 (1991). To be independent, the "state court
must actually have relied on the procedural bar as an independent basis for its disposition of the
15

case," by "clearly and expressly stat[ing] that its judgment rests on a state procedural bar."
Harris v. Reed, 489 U.S. 255,261-62 & 263, 109 S.Ct. 1038 (1989) (internal quotation marks
omitted). A procedural rule is adequate if it is "firmly established and regularly followed by the
state in question." Garcia v. Lewis, 188 F.3d 71, 77 (2d Cir. 1999) (internal quotation marks
omitted). "[P]rinciples of comity ... counsel that a federal court that deems a state procedural
rule inadequate should not reach that conclusion lightly or without clear support in state law."
ld. at 77 (internal quotation marks omitted).
The decision of the§ 440 court in the instant case satisfies the requirement of
independence, as the appeal waiver was expressly relied upon as dispositive, regardless of the
merits of petitioner's claim. See Jimenez v. Walker, 458 F .3d 130 (2d Cir. 2006) (where state
court specifically refers to a procedural bar, alternative holding on the merits does not eliminate
federal court's obligation on habeas review to defer to procedural bar). However, the adequacy
of the procedural bar presents a different question.
Respondent's attempt to defend the procedural bar invoked here is at least simplistic and
possibly misleading. To show regular application of appeal waivers, respondent has cited to
New York decisions that stand for the unremarkable proposition that appeal waivers are upheld
under New York law. See, e.g., People v. Kemp, 94 N.Y.2d 831, 703 N.Y.S.2d 59 (1999);
People v. Muniz, 91 N.Y.2d 570,673 N.Y.S.2d 358 (1998) (written waiver of appeal enforced
against double-jeopardy claim). However, as he did before the§ 440 court, respondent has
neglected to cite cases dealing with the effect of appeal waivers on claims of ineffective
assistance of counsel. Those cases tell a different story. It is clear, contrary to respondent's
assertion that the§ 440 court's invocation of the waiver was "consistent with a well-established
practice in New York of holding criminal defendants to their agreements when they waive
16

postconviction review as part of a negotiated plea bargain," that state courts will hear ineffective
assistance of counsel claims notwithstanding an appeal waiver under certain conditions. See
36A Carmody-Wait 2d § 207:14 (database updated Juue 2011) ("[A] defendant's contentions
that his or her waiver of the right to appeal was not voluntarily, knowingly, and intelligently
made and that he or she was denied effective assistance of counsel survive the waiver of the right
to appeal inasmuch as the alleged deficiencies impact the plea.").
To survive the waiver, according to the New York courts, the claim of ineffective
assistance must directly pertain to the defendant's decision to plead guilty- in other words, the
claim must "go to the very heart of the process." People v. Parilla, 8 N.Y.3d 654,659, 838
N.Y.S.2d 824 (2007) (quoting People v. Hanse11 95 N.Y.2d 227,230, 715 N.Y.S.2d 369 (2000)).
This emphatically does not include missed opportunities to seek dismissal or other errors in
pretrial proceedings distinct from the plea negotiation process itself. See id.; People v. Di
Raffaele, 55 N.Y.2d 234,448 N.Y.S.2d 448 (1982) (claims ofpreindictment prosecutorial
misconduct foreclosed by waiver); People v. Friscia, 51 N. Y.2d 845, 433 N .Y.S.2d 754 (1980)
(speedy trial claims foreclosed by waiver). These cases express the same concern as has the
Second Circuit in this context - if a defendant decides to plead guilty based on erroneous advice
on a material point given in the context of his decision to plead guilty, then the resulting plea
cannot be truly "knowing and voluntary." See, e.g., People v. Finkelstein, 25 A.D.3d 456,457,
807 N.Y.S.2d 97 (1st Dep't 2009) ("Although defendant waived his right to appeal, his claim
that his attorney rendered ineffective assistance ... is reviewable to the extent it affects the
voluntariness of his plea .... ").
Perhaps the strongest support for the§ 440 court's decision is a case that respondent has
not cited here: the New York Court of Appeals' decision in Parilla. There, the defendant had an
17

ostensible argument that the statute of limitations barred the claim against him. On the eve of
trial, he considered accepting a plea agreement. Through counsel, he inquired of the court
(seeking, in effect, an advisory opinion) as to whether the court would grant a motion to dismiss
based on the statute of limitations. The court obliged, and advised him that such a motion would
be denied because there was a statutory toll. The defendant thereupon accepted the plea offer,
which included an appeal waiver. After sentencing, he challenged his plea in a consolidated
direct appeal and collateral proceeding, arguing that his counsel was ineffective for having failed
to move to dismiss on statute of limitations grounds. The Court of Appeals upheld the appeal
waiver and declined to hear the claim:
[T]his is not a case where the alleged ineffectiveness of counsel goes to the
voluntariness of defendant's plea and waiver of appeal. To the contrary, the
record establishes that defendant's plea was intelligent, voluntary and knowing.
Before he pleaded guilty, defendant was aware of the potential statute of
limitations defense and the possible application of the CPL§ 30.10(4)(a)(ii) tolling
provision. After having an opportunity to weigh his options, defendant chose not
to assert the defense, declined his right to a jury trial and waived his right to raise
the limitations argument on appeal.
Parilla, 8 N.Y.3d at 660.
It seems clear that the "connectivity" standard in the Second Circuit's Parisi decision
limits the effectiveness of appeal waivers far more than the New York Court of Appeals' "heart
of the process" standard in Parilla. In Parisi, the appeal waiver was avoidable based on the
failure of trial counsel to seek dismissal on speedy trial grounds; in Parilla, the waiver could not
be avoided by the failure of trial counsel to seek dismissal on statute oflimitations grounds. The
cases cannot be reasonably reconciled.
Although both Courts' standards go to the issue of whether a defendant's guilty plea is
knowing and voluntary, which is undoubtedly a question of constitutional magnitude, see

18

McMahon v. Hodges, 382 F.3d 284, 289-90 (2d Cir. 2004), it is not clear whether the breadth of
the Second Circuit's standard is one of constitutional interpretation or resulted solely in the
exercise of its supervisory power over federal appeal waivers. It may well be that the New York
Court of Appeals' narrower "heart of the process" standard is all that the Constitution requires,
and if so, then procedural bars imposed by the New York courts in accordance with Parilla
would constitute independent and adequate state law grounds to preclude federal review.
However, I need not resolve that issue because the procedural bar imposed by the § 440
court went beyond the scope of permissible waivers, not only, most certainly, under Parisi, but
also under Parilla and all of the other state court authorities cited above. In reaching this
conclusion, I recognize that, at first blush, there are some similarities between the instant case
and Parilla. In both cases, the defendant and his lawyer identified a legal issue on the eve of trial
that weighed upon the defendant's decision whether to plead; discussed it with the court; and
decided to forego the legal issue in favor of pleading guilty. Nevertheless, the dissimilarities
between the alleged errors of counsel are more important. The error of Parilla' s counsel was the
failure to assert an affirmative defense to prosecution that was wholly separate from the plea
agreement. In this case, however, the alleged error went toward the key provision of how
petitioner's term of imprisonment would be calculated; that error was itself the basis for the plea
bargain.
As suggested above, I can think of no issue that goes more to "the heart ofthe process"
than whether or not petitioner's prior New Jersey conviction would count in his sentencing.
Petitioner's agreed-upon term of imprisonment was directly dependent on the ability, or lack of
ability, of his lawyer to understand the application of a foreign conviction under N.Y. Pen. L. §
70.08(1)(a). If, as petitioner alleges (and, as discussed below, the record supports), his attorney
19

lacked even the most basic knowledge of how to make this analysis, then the guilty plea that
petitioner gave was the result of his lawyer's bad advice in the most direct way.
A case cited by respondent in passing, People v. De Aga, 74 A.D.3d 552, 903 N.Y.S.2d
39 (1st Dep't 2010), is a strong indication that the procedural rule invoked by the§ 440 court
here was not "regularly followed" by New York courts. De Aga involved the issue of whether
another section ofthe same statute at issue here, N.J. Stat. § 2C: 12-1, could serve as a predicate
felony under N.Y. Pen. L. §70.04(1 )(b)(i), and concluded in no uncertain terms that it could not.
The Court reached out under its interest-of-justice jurisdiction to vacate the plea, finding the
point so compelling that it was unnecessary to consider the defendant's concurrently-pending§
440 proceeding. The Court explained that the legal mistake - construing N.J. Stat. § 2C: 12-1 as
a qualifying predicate New York felony- was so intertwined with the plea negotiation process as
to render the defendant's plea involuntary:
Misinformation as to defendant's status impacted plea negotiations. The parties
were under the misapprehension that defendant was receiving the most lenient
disposition permitted by law. Furthermore, whether defendant was a first felony
offender or a second violent felony offender made a dramatic difference in the
minimum sentence upon a conviction after trial . . . . These misapprehensions
may have affected the People's offer, as well as defendant's decision to accept it.
De Aga, 74 AD .3d at 553. De Aga thus supplies further indication that petitioner's ineffective
assistance of counsel claim goes "to the heart of the process."
The§ 440 court's application of the waiver as a procedural bar to petitioner's claim was
therefore improper under state law. The procedural bar thus cannot be considered "firmly
established and regularly followed" by New York courts, see Garcia, 188 F .3d at 77, and is
inadequate to preclude petitioner's collateral attack in federal court.

20

IV
After determining that petitioner's claims were procedurally barred, the§ 440 court
alternatively denied his claims on the merits. The scope of my review of petitioner's Sixth
Amendment claim is therefore limited. Under the Antiterrorism and Effective Death Penalty Act
of 1996 ("AEDPA"), a federal court may grant a vvrit of habeas corpus to a state prisoner on a
claim that was "adjudicated on the merits" in state court only if it concludes that the adjudication
of the claim "(1) resulted in a decision that was contrary to, or involved an unreasonable
application of, clearly established Federal law, as determined by the Supreme Court ofthe
United States; or (2) resulted in a decision that was based on an unreasonable determination of
the facts in light of the evidence presented in the State court proceeding." 28 U.S.C. § 2254(d).
Determination of factual issues made by a state court "shall be presumed to be correct," and the
petitioner "shall have the burden of rebutting the presumption of correctness by clear and
convincing evidence." Id. § 2254(e)(1). The fact that the state court did not fully articulate all
possible grounds for rejecting the claim on the merits does not deprive its decision of this
deferential standard of review. See Jimenez, 458 F.3d at 143.
An "adjudication on the merits" is a "substantive, rather than a procedural, resolution of a

federal claim." Sellan v. Kuhlman, 261 F.3d 303,313 (2d Cir. 2001). A decision is "contrary
to" clearly established federal law if"the state court arrives at a conclusion opposite to that
reached by [the Supreme Court] on a question oflaw" or if the state court "confronts facts that
are materially indistinguishable from a relevant Supreme Court precedent and arrives at a result
opposite to [the Supreme Court's result]." Williams v. Taylor, 529 U.S. 362, 405, 120 S.Ct.
1495 (2000). A decision is "an unreasonable application" of clearly established federal law if a
state court "identifies the correct governing legal rule from [the Supreme Court's] cases but

21

unreasonably applies it to the facts of the particular state prisoner's case." Id. at 407. For relief
to be warranted, the "state court's application of governing federal law ... must be shown to be
not only erroneous, but objectively unreasonable." Waddington v. Sarausad, 555 U.S. 179, 190,
129 S.Ct. 823 (2009) (internal quotation marks omitted).
To prevail on a claim of ineffective assistance of counsel under the Sixth Amendment, a
petitioner must satisfy the two-part inquiry set forth in Strickland. First, he must first show that
his "counsel's representation fell below an objective standard of reasonableness," Strickland,
466 U.S. at 688, and that counsel made errors serious enough to violate defendant's guarantee of
counsel via the Sixth Amendment. See Hill v. Lockhart, 474 U.S. 52, 59, 106 S.Ct. 366 (1985).
In evaluating that issue, I must "'indulge a strong presumption that counsel's conduct falls within
the wide range of reasonable professional assistance."' United States v. Aguirre, 912 F.2d 555,
560 (2d Cir. 1990) (quoting Strickland, 466 U.S. at 689). Second, petitioner "must show that the
deficient performance prejudiced the defense." Strickland, 466 U.S. at 687. This means "that
there is a reasonable probability that, but for counsel's unprofessional errors, the result of the
proceeding would have been different." Id. at 694.
In denying petitioner's ineffective assistance claim on the merits, the§ 440 court did not
cite Strickland and did not describe either prong of the Strickland analysis. With regard to the
merits of petitioner's entire§ 440 application, the court stated:
[S]uch application has no merit. Prior to entering into a plea, the defendant fully
discussed his prior New Jersey conviction with his attorney. The defendant also
reviewed his own research with his lawyer. The prosecution and defense counsel
agreed that defendant was not a mandatory persistent felony offender but that
upon pleading guilty, he faced sentencing as a second violent felony offender
who's [sic] predicate conviction was for a violent felony offense. The defendant
then entered into a plea of guilty on this instant case. The allegation that his
attorney was ineffective for permitting him to admit this prior New Jersey felony
conviction has no legal or factual support whatsoever.
22

Although purporting to reject the Sixth Amendment claim on the merits, the court did not engage
in a Strickland analysis. In this paragraph, the court merely recites the facts of petitioner's case
and proceeds to summarily reject his Sixth Amendment claim.
When the state courts have "summarily rejected" an ineffective assistance of counsel
claim on the merits, a district court considering that claim under AEDPA should "turn directly to
the facts of the case to determine whether Strickland was applied unreasonably." Cox v.
Donnelly, 387 F .3d 193, 197 (2d Cir. 2004). In this situation, a district court's inquiry "must
focus on the ultimate decisions of those courts, rather than on the courts' reasoning." Davis v.
Greiner, 428 F.3d 81, 88 (2005) (internal quotation marks omitted). To find that the state court's
ultimate decision was objectively unreasonable, a court "must find that there was some
increment of incorrectness beyond error." Davis, 428 F.3d at 88 (internal quotation marks
omitted).

A.
As to Strickland's first factor, even respondent does not dispute that the advice petitioner
received here, and the argument that the prosecutor made and the trial court accepted, was
wrong. The New Jersey assault statute is not a qualifying felony for second violent felony
offender status under New York law. The method for determining when a foreign conviction
constitutes a qualifying felony is set forth in N.Y. Pen. L. § 70.04, which basically provides that
a foreign conviction will count if it has "the same elements" as a qualifying New York violent
felony, all of which are listed in N.Y. Pen. L. § 70.02. New York law generally limits the
comparative inquiry to the face of the New York and foreign statutes. See People v. Muniz, 74
N.Y.2d 464,467-68,548 N.Y.S.2d 633 (1989).

23

Under the New Jersey statute and the face of petitioner's New Jersey indictment (which
merely repeated the language of the statute), the New Jersey assault does not qualify as a
predicate violent felony in New York. The elements of the New Jersey assault statute and New
York's assault statute are obviously different, and the New Jersey assault statute criminalizes
much less egregious conduct in two respects. First, the New York statute requires use of a
deadly weapon, whereas the New Jersey assault statute does not require any weapon. Second,
the New Jersey assault statute is violated if a defendant causes a police officer "pain," whereas
the New York statute requires that a defendant subject a police offer to injury causing "a
substantial risk of death, or which causes death or serious and protracted disfigurement,
protracted impairment of health or protracted loss or impairment of the function of any bodily
organ." N.Y. Pen. L. § 10.00(10). Thus, for example, based on the face of the New Jersey
assault statute and petitioner's indictment, petitioner could have been convicted in New Jersey
for punching a police officer. That, without more, would not rise to the level of New York's
aggravated assault statute, and thus the New Jersey conviction was improperly counted as a
predicate felony.
Respondent correctly notes that not every mistake made by a lawyer is objectively
unreasonable. For example, an attorney's reasoned tactical choice cannot be second-guessed on
habeas corpus review even if, with the benefit of hindsight, the choice appears erroneous. See
Strickland, 466 U.S. at 690-91. Similarly, when advising a defendant or taking an approach that
is a matter of judgment, the fact that the judgment appears later to have been erroneous does not
necessarily mean that the attorney was objectively unreasonable. See id.
But according to petitioner's description of the events, which respondent does not
dispute, that is not what happened here. Petitioner avers that his discussions with his lawyer

24

showed that the lawyer had no understanding, not only of the elements of the New Jersey assault
statute, but of the basic New York principle that the issue in comparing the foreign statute to its
New York counterpart is whether the elements of the crime are the same. 6 Instead, petitioner's
trial counsel was of the firm view, consistent with the prosecutor's position, that the New Jersey
conviction qualified as a predicate felony because both the New York and the New Jersey
statutes pertained to an assault on a police officer. There is no support whatsoever for the
position under New York law that foreign crimes with similar-sounding names to New York
crimes constitute predicate felonies. There is thus no tactical decision here and no judgment call.
There is simply a lack of knowledge.
The §440 court was of the view that petitioner's legal sophistication, demonstrated by his
having convinced his lawyer, the prosecutor, and the judge that his two New Jersey
misdemeanors did not "count," should be considered as part of the ineffective assistance
analysis. I disagree. Regardless of a defendant's sophistication, it is objectively unreasonable
for a New York defense lawyer to lack knowledge of the basic principles of enhanced sentencing
status under New York law when his client is facing enhanced sentencing.
In Mask v. McGinnis, 28 F. Supp. 2d 122 (S.D. N.Y. 1998), for example, the prosecutor

and defense counsel had operated under the assumption that the petitioner would be sentenced as
a persistent violent felony offender because he had two prior felony convictions. Based on this
assumption, the prosecutor refused to make an offer of less than ten years, and the petitioner
chose to proceed to trial, where he was convicted and sentenced to at least twenty years in

6

For this reason, cases under 28 U.S.C. § 2255 that decline to find ineffective assistance due to the miscalculation of
the federal sentencing guidelines are inapposite. "Because the prediction of a guidelines range is necessarily an
estimate of a determination left to the Court's discretion, a mistaken calculation is generally not akin to 'erroneous
legal advice about the ultimately knowable.'" United States v. Guidice, No. 02-729, 2004 WL 1152539, *5
(S.D.N.Y. May 21, 2004) (quoting United States v. Sweeney, 878 F.2d 68,70 (2d Cir. 1989)).

25

prison. As to one of his prior convictions, however, petitioner had not yet been sentenced and
judgment had not yet been entered. Under the plain language ofN.Y. Pen. L. § 70.08, this meant
that the conviction should not have counted for enhanced sentencing status. On habeas corpus
review, then-District Judge Chin found that "[a]s a consequence of defense counsel's failure to
detect the prosecutor's error, the prosecution, the defense, and the trial court all operated under
the mistaken impression that petitioner had to be sentenced as a violent persistent felony
offender," Mask, 28 F. Supp. 2d at 125, and that trial counsel's failure to have basic familiarity
with the New York statute was objectively unreasonable. Accord, Somerville v. Conway, 281 F.
Supp. 2d 515, 523 (E.D.N.Y. 2003) (Where habeas petitioner was wrongly sentenced in state
court as second violent felony offender because of improper counting of foreign conviction, trial
counsel's failure to argue the point was objectively unreasonable because "it would not have
required exceptional measures for a defense lawyer to become familiar with the pertinent statutes
and case law.").
Finally, I note that the presence of a sentencing issue arising from the law of a state other
than New York does not make counsel's lack of knowledge of how to analyze that conviction
less objectively unreasonable. First, the seminal problem here was trial counsel's unfamiliarity
with the principle of New York law on how to treat foreign convictions. Had he known that, he
would have required no additional knowledge of New Jersey law beyond the simple language of
the assault statute and the one other statutory provision that defined the term "bodily injury"
(both of which statutes his client provided him, and are quoted in note 1, supra). Furthermore,
criminal defense counsel is expected to be familiar with provisions of law that might go beyond
daily trial practice if those provisions have meaningful consequences with regard to his client's
guilty plea. See Padilla v. Kentucky, 130 U.S. 1473 (2010).

26

I therefore hold that the §440 court unreasonably applied ~trickland in determining that
petitioner's counsel was objectively reasonable.

B.
The only potential factual question raised on this record is whether petitioner satisfies
Strickland's second factor, namely, whether he was prejudiced by his counsel's bad advice.
The Supreme Court has explained that, when a petitioner challenges his sentence,
Strickland prejudice may be demonstrated upon a showing that the ineffective assistance resulted
in a sentencing difference of"any amount of actual jail time." Glover v. United States, 531 U.S.
198, 203, 121 S.Ct. 696 (2001). When a petitioner challenges a sentence imposed after
conviction at trial, for example, courts have found Strickland prejudice upon a showing that
counsel could have secured a more favorable sentence through effective pre-trial plea bargaining.
See Puglisi v. United States, 586 F.3d 209, 215 (2d Cir. 2009) (when a petitioner rejects a plea
offer for a sentence lighter than the sentence ultimately received after trial, prejudice is
demonstrated by showing that "but for counsel's improper advice, the petitioner would have
accepted the plea offer"•) (citing Aeid v. Bennett, 296 F.3d 58, 62-63 (2d Cir. 2002)); United
States v. Gordon, 156 F.3d 376 (2d Cir. 1998) (asking whether there was a "reasonable
probability" that, but for the alleged ineffectiveness of counsel, a plea bargain would have been
offered to and accepted by petitioner); Dobbin v. Greiner, No. 00-7085,2007 WL 414986, at *3
(S.D.N.Y. Jan. 31, 2007) (same); Mask, 233 F.3d at 140.
Here, petitioner asserts that he is challenging the sentence based on his counsel's
ineffectiveness during the plea bargaining process. It is implicit in petitioner's argument that he
is also challenging his counsel's performance during the sentencing, as his counsel could
obviously have raised this issue at any point prior to sentencing.
27

This second Strickland factor is often not free from doubt, as it requires resolution of a
hypothetical situation that has not occurred. Here, as is often the case, the hypothetical is at least
double~ faceted: (1) if petitioner's trial counsel had analyzed and argued to the prosecutor and

the trial court that petitioner's New Jersey aggravated assault would not support second violent
felony offender status, would the prosecutor have offered eight years; and (2) if the prosecutor
had offered eight years, would petitioner have accepted it?
Notwithstanding the deferential standard under 28 U.S.C. § 2254(e)(l), I hold that
petitioner has demonstrated by clear and convincing evidence that had his lawyer properly
advocated on his behalf, he would have received and accepted an eight year plea agreement and
sentence. As to the second issue identified above - would petitioner have taken an eight year
plea agreement- there can be little if any doubt. Petitioner's position when he pled guilty,
during his § 440 proceeding, and in this habeas petition makes it clear that he was going to plead
guilty to the best deal he could get. He was aware of the evidence against him and did not want
to go to trial.
The first issue is not as clear because there is no evidence in the record from the
prosecutor. Nevertheless, the circumstantial evidence strongly suggests the conclusion that, if
the prosecutor knew that New York law did not permit petitioner to be sentenced as a second
violent felony offender, the prosecutor would have offered him a sentence of eight years. This
was not a case where there prosecutor was demanding the high- or even middle-end of the
potential sentencing range, nor was it a case where the prosecutor expressed any intransigence
about making a plea agreement. He first offered to allow petitioner to plead to a lesser crime,
with a twelve-year determinate sentence, when he thought that petitioner's three New Jersey
convictions should count as predicate felonies; when he learned that two of the offenses did not
28

count as predicate felonies, he quickly dropped to ten years, which was the mandatory minimum
for a second violent felony offender. It therefore logically follows that, if it had been pointed out
to him that the New Jersey aggravated assault conviction could not count either, he would have
offered the bottom of the new sentencing range. It would strain credulity to hold, as the§ 440
court implicitly did, that a prosecutor who was willing to bargain down to a ten-year term rather
easily would insist on trial rather than offer eight years once it was pointed out to him that the
basis for the ten-year term was legally erroneous.
I recognize that it is not impossible. The prosecutor could have concluded that ten years
was as low as he was willing to go. He might have reasoned, if faced with the illegality of
sentencing petitioner as a second violent felony offender, that notwithstanding the inability to
count the New Jersey convictions, petitioner's criminal history was sufficiently egregious that he
was going to offer no less than ten years. The prosecutor was not obligated to offer a plea
agreement at all, much less to offer an agreement at the bottom of the applicable sentencing
range.
Respondent asserts that it is mere speculation as to whether an eight-year agreement
would have been offered. As noted above, there are sufficient reasons on this record to support a
conclusion to the contrary. Moreover, petitioner can hardly be blamed for any deficiency of
proof in this regard, given the§ 440 court's determination not to hold a hearing and the fact that
only respondent has access to the prosecutor. Any uncertainty in the issue beyond these facts is
inherent in the context of examining the Strickland prejudice factor. 7 Thus, I conclude that it is

7

To the extent there is any issue as to whether the state court would have accepted an eight-year plea agreement, I
fmd based on its willingness to accept the twelve or ten-year agreement that it would also accepted an eight-year
agreement. There is no indication on the record that the trial court would have insisted on the case going to trial if
the parties' agreement was for eight years.

29

far more speculative to believe that the prosecutor would have gone to trial instead of offering an
agreement with two years less than he had proposed accepting.
In any event, to demonstrate prejudice, petitioner needs only to demonstrate a
"reasonable probability," see Strickland, 466 U.S. at 695, that if his trial counsel had effectively
argued the correct standard for evaluating the New Jersey assault conviction, the prosecutor and
the trial court would have agreed to a plea agreement for a term of eight years. All of the
discussions on the record were directed toward a proposal for a determinate sentence at the low
end of petitioner's sentencing status, whatever that was. There is nothing to suggest that the
prosecutor would have insisted on a term in excess of petitioner's lowest available sentencing
exposure under properly-applied New York law. Petitioner therefore clearly demonstrated to the
§ 440 court a "reasonable probability" that he was prejudiced by his counsel's ineffective
assistance, and the§ 440 court unreasonably applied Strickland in holding to the contrary.
In making this finding, I concede that the meaning of "unreasonable" in this context is
rather elusive. The Supreme Court has cautioned that "an unreasonable application of federal
law is different from an incorrect or erroneous application of federal law." Williams, 529 U.S.
at 412. In the Second Circuit, this means that the state court's application of federal law "must
reflect some additional increment of incorrectness such that it may be said to be unreasonable."
Aparicio v. Artuz, 269 F.3d 78, 94 (2d Cir. 2001). However, the Second Circuit also maintains
that this increment "need not be great; otherwise, habeas relief would be limited to state court
decisions so far offthe mark as to suggest judicial incompetence." Id. (internal quotation marks
omitted). Here, there is no credible evidence that the prosecutor would have demanded a trial
over a two-year difference, and all of the facts point to the contrary conclusion.

30

v
The writ of habeas corpus is granted to the extent that petitioner's guilty plea is vacated,
unless respondent consents to the imposition of an eight-year sentence, together with any other
conditions attendant to the sentence previously imposed, within 120 days. See generally United
States v. Carmichael, 216 F.3d 224,227 (2d Cir. 2000).
SO ORDERED.

--

--~--.,~--

Dated: Brooklyn, New York
October 3, 2011

31