Simard v. United States of America

Filing 2

OPINION AND ORDER Report and Recommendation is not adopted; granting 1 Motion to Vacate, Set Aside, or Correct Sentence (2255). Signed by Judge William K. Sessions III on 11/5/2019. (jam)

UNITED STATES DISTRICT COURT
FOR THE
DISTRICT OF VERMONT
UNITED STATES OF AMERICA

)
)
)
)
)

v.
SHAWN SIMARD

Case No. 2:10-cr-47

OPINION AND ORDER
Defendant Shawn Simard, through counsel, has moved pursuant
to 28 U.S.C. § 2255 to set aside the judgment in this case and
correct his sentence.

Simard requests re-sentencing because the

prior state court conviction used to enhance his federal sentence
has since been vacated.

The government does not contest the

substance of Simard’s request, but opposes the motion as untimely
and for lack of due diligence in pursuing post-conviction relief
in state court.
Magistrate Judge John M. Conroy issued a Report and
Recommendation recommending denial of Simard’s motion for lack of
due diligence.
Recommendation.

Simard has filed an objection to the Report and
For the reasons set forth below, the Court finds

that Simard’s Section 2255 motion is not untimely, and that given
the lack of clarity in Vermont law, the advice received from
counsel, and the challenges specific to Simard while
incarcerated, his pursuit of post-conviction review in state
court did not lack due diligence.
relief is therefore granted.

The motion for habeas corpus

Standard of Review
A district judge must make a de novo determination of those
portions of a magistrate judge’s report and recommendation to
which an objection is made.

Fed. R. Civ. P. 72(b); 28 U.S.C. §

636(b)(1); Cullen v. United States, 194 F.3d 401, 405 (2d Cir.
1999).

The district judge may accept, reject, or modify, in

whole or in part, the findings or recommendations made by the
magistrate judge.
at 405.

28 U.S.C. § 636(b)(1); accord Cullen, 194 F.3d

A district judge is not required to review the factual

or legal conclusions of the magistrate judge as to those portions
of a report and recommendation to which no objections are
addressed.

Thomas v. Arn, 474 U.S. 140, 150 (1985).
Background

Simard is currently serving a federal sentence after
pleading guilty to possession of child pornography in violation
of 18 U.S.C. § 2252(a)(4)(B).

At his August 13, 2012 sentencing,

Simard faced a mandatory minimum term of ten years in prison as a
person previously convicted of sexually abusing a minor.
U.S.C. § 2252(b)(2).

See 18

The underlying offense was a 2004 state

court conviction for lewd and lascivious conduct with a child in
violation of 13 V.S.A. § 2602.
With an adjusted offense level of 30 and a Criminal History
Category of III, Simard’s advisory Guideline range was 121-151
months.

The Court sentenced him to 121 months in prison, to be
2

followed by 15 years of supervised release.

Simard pursued a

direct appeal, and the Second Circuit affirmed his sentence.

The

Supreme Court denied his petition for a writ of certiorari on
April 21, 2014.
Simard’s state court conviction was vacated in 2016.
According to his state petition for post-conviction relief, filed
by the Vermont Prisoners’ Rights Office on February 16, 2016, the
trial court never asked Simard during his change of plea colloquy
whether he admitted to the facts establishing the elements of the
crime.

Instead, the court asked whether he understood the

charge, and the only agreement to underlying facts came from
defense counsel.

ECF No. 114-1 at 1.

As discussed below, Vermont law has been unclear in recent
years about the requirements of Rule 11 plea proceedings.

In

Simard’s case, the State stipulated to granting his postconviction review petition, and on April 11, 2016 the state court
signed the Entry Order vacating his state court conviction.1

The

vacatur re-opened the criminal proceeding, and the charge against
Simard has since been dismissed.

Simard filed his Section 2255

motion on April 10, 2017.

1

The government argues that the state court actually
vacated Simard’s sentence on April 5. While the state court
docket does include an entry reflecting vacatur on April 5 (ECF
No. 107-2 at 3), the written Entry Order is dated April 11 (ECF
No. 119-2 at 1). Moreover, the Magistrate Judge found that the
state court vacated the conviction on April 11, 2016 (ECF No. 120
at 6), and the government has not challenged that conclusion.
3

Discussion
In Johnson v. United States, 544 U.S. 295, 302 (2005), the
Supreme Court held that a state court’s decision vacating a prior
conviction is a “fact” that restarts the Section 2255 one-year
limitation period, so long as the defendant sought vacatur of his
conviction with due diligence.

Johnson found that a defendant

must move for relief in state court “as soon as he is in a
position to realize that he has an interest in challenging the
prior conviction with its potential to enhance the later
sentence,” and that the duty to act with due diligence begins on
“the date of judgment” in his federal case.

544 U.S. at 308-09.

Here, the government submits that Simard failed to file his
Section 2255 motion within the one-year limitations period.

As

noted above, Simard filed his motion within one year of the Entry
Order vacating his state court conviction.

His filing was

therefore timely.
The government also contends that Simard failed to satisfy
Johnson’s due diligence requirement.

The Second Circuit has

determined that the federal habeas corpus statute “does not
require the maximum feasible diligence, only ‘due,’ or reasonable
diligence.”

Wims v. United States, 225 F.3d 186, 190 n.4 (2d

Cir. 2000); see also Jefferson v. United States, 730 F.3d 537,
544 (6th Cir. 2013).

“Due diligence therefore does not require a

prisoner to undertake repeated exercises in futility or to
4

exhaust every imaginable option, but rather to make reasonable
efforts.”

United States v. Longshore, 644 F. Supp. 2d 658, 661

(D. Md. 2009) (citing Aron v. United States, 291 F.3d 708, 712
(11th Cir. 2002)).
In this case, there are arguably two delays at issue.

The

first is the period of time between Simard’s federal sentencing
and the emergence of Vermont case law clarifying his right to
relief in state court.

The second is the alleged delay between

that clarification and Simard’s filing of a state court petition
for post-conviction review.
With respect to the first period of alleged delay, Simard
submits that his right to relief in state court was not clear at
the time of his federal conviction.

Indeed, the precise contours

of lawful Rule 11 plea proceedings in Vermont were, until
recently, unsettled.

See In re Bridger, 2017 VT 79, ¶ 28, 205

Vt. 380, 396, 176 A.3d 489, 499 (“Although we have decided many
Rule 11 cases, I think we have failed to achieve clear
requirements that can be implemented correctly in thousands of
cases.”) (Dooley, J., concurring).

Prior to Simard’s 2004 state

court plea, State v. Yates, 169 Vt. 20, 27, 726 A.2d 483, 488
(1999) required that a defendant personally admit to the factual
basis for the charge.

Shortly thereafter, however, the Vermont

Supreme Court in State v. Morrissette, 170 Vt. 569, 571, 743 A.2d
1091, 1093 (1999) (mem.) upheld a conviction where the defendant

5

had signed a waiver-of-rights form and stipulated to the
underlying facts through his attorney.

Citing the memorandum

decision in Morrissette, State v. Cleary, 2003 VT 9, ¶ 29, 175
Vt. 142, 153, 824 A.2d 509, 518 affirmed the defendant’s
conviction where the underlying facts were agreed to by counsel.
The Cleary court found that because the underlying police
affidavit was acknowledged by the defendant, and the factual
basis agreed to by counsel, “the factual basis was in effect
stipulated to and admitted by defendant.
substantial compliance with Rule 11.”

Thus, there was

Id. ¶¶ 29, 30.

In his

Cleary dissent, Justice Dooley opined that the memorandum
decision in Morrissette had “sub silentio overruled the
one-year-old decision in Yates.”

Id. ¶ 61.

On March 21, 2014, the Vermont Supreme Court issued In re
Stocks, 2014 VT 27, 196 Vt. 160, 94 A.3d 1143, holding that a
defendant who pleads guilty must admit on the record to the
factual basis for the charge.

Stocks was in accord with Yates

but did not expressly overrule Cleary.

See In re Bridger, 2017

VT 79, ¶ 28 (noting that Stocks did not “explicitly overrul[e]”
Cleary).

On August 24, 2014, the Vermont Supreme Court held in

In re Manosh, 2014 VT 95, 197 Vt. 424, 108 A.2d 212 that a
defendant’s written waiver of rights could not substitute for an
open colloquy in court.

Manosh overruled Morrissette to the

extent that a trial court must personally address the defendant
6

and explain his rights in open court.

2014 VT 95, ¶ 23.

In 2017, the Vermont Supreme Court’s Bridger decision
reinforced Yates, overruled Cleary, and clarified its rejection
of Morrissette.

Bridger first explained that, according to

longstanding Vermont precedent, Rule 11(f) requires an admission
on the record from the defendant.

2017 VT 79, ¶ 11 (“[W]e have

consistently concluded that an ‘adequate factual basis’
sufficient to demonstrate voluntariness must consist of some
recitation on the record of the facts underlying the charge and
some admission by the defendant to those facts.”) (citing Yates,
726 A.2d at 48).

The court also noted that, “unfortunately,

State v. Morrissette and State v. Cleary inadvertently sowed
confusion by importing the phrase ‘substantial compliance’ into
our Rule 11(f) jurisprudence.”

Id. ¶ 18.

Although Morrissette

did not involve a Rule 11(f) challenge, Cleary “relied
exclusively on Morrissette to deny the defendant’s Rule 11(f)
challenge because the trial court ‘substantially complie[d]’ with
Rule 11(f).”

Id. ¶ 20.

Because Cleary was inconsistent with

pre-existing Vermont precedent, and “[t]o the extent Cleary
relied on Morrissette and the ‘substantial compliance’ standard,”
Cleary was overruled.

Id.

Bridger also stated that “[a]lthough

we did not explicitly refer to the ‘substantial compliance’
standard when we overruled Morrissette, we now make explicit what
Manosh made implicit: ‘substantial compliance’ has no place in
7

Rule 11(f) claims.”

Id.

Most recently, when considering the question of Bridger’s
retroactive effect, the Vermont Supreme Court clarified which
portions of Bridger announced new rules of law.
2018 VT 78, 195 A.3d 364.

In re Barber,

Barber identified three main holdings

in Bridger: (1) the defendant must personally admit to the facts
underlying the charge, (2) oral or written stipulations or
waivers cannot substitute for an oral admission by the defendant,
and (3) substantial compliance does not apply to Rule 11(f)
challenges.

Id. ¶ 11.

With respect to the first holding, Barber

cited the discussion in Bridger about longstanding Vermont case
law requiring an on-the-record admission by the defendant, and
determined that the holding “did not establish a new rule.”
¶ 10.

Id.

The second holding, pertaining to oral or written

stipulations, is of questionable application here as there is no
record evidence of a stipulation by Simard in his state court
case.
The third Bridger holding erases any doubt about whether
substantial compliance has a role in Rule 11(f) proceedings.
Barber determined that
Bridger’s holding that substantial compliance does not
apply to evaluating claims under Rule 11(f) was a new
rule because it was not dictated by existing precedent
and required overruling prior case law. The majority
itself recognized that this Court’s prior cases were
not uniform on the question of whether substantial
compliance applied in Rule 11(f) cases and explicitly
8

overruled prior case law that allowed such application.
Id. ¶ 13.

That clarification is relevant here.

The question of due diligence in this case centers in part
on whether, prior to Stocks, Manosh, Bridger and Barber, Simard
was “in a position to realize that he ha[d] an interest in
challenging the prior conviction.”

Johnson, 544 U.S. at 308.

The government argues that Yates was the controlling precedent,
and that Stocks merely reaffirmed the Yates holding.

Simard

contends that with Morrissette and Cleary standing as good law,
it was not until Stocks, Manosh, and arguably Bridger that such
relief became readily available.

The Vermont Supreme Court

itself acknowledged in Bridger that Morrissette and Cleary had
caused confusion, and Justice Dooley noted in his concurrence a
lack of clear requirements for Rule 11 proceedings.
Simard moved for post-conviction relief in 2016, 18 months
after Manosh overruled Morrissette, but prior to Bridger’s clear
rejection of the “substantial compliance” standard.
¶ 20.

2017 VT 79,

His timing was due, in part, to the initial advice

received from attorneys who were undoubtedly aware of the
“substantial compliance” case law.

If, for the sake of argument,

Simard received poor legal advice, it is not clear how quickly he
should have discovered counsel’s error, particularly given the
uncertainties in the law.

Cf. Ryan v. United States, 657 F.3d

604, 607 (7th Cir. 2011) (“No rule of thumb emerges from the
9

cases on how long prisoners may take to discover their lawyers’
missteps, and we hesitate to pick a magic number.”).
Of course, in addition to the legal uncertainties, the Court
may take into account the conditions of Simard’s incarceration.
See Wims, 225 F.3d at 190–91 (noting that conditions of
confinement may be considered when determining the commencement
of a limitations period); Easterwood v. Champion, 213 F.3d 1321,
1323 (10th Cir. 2000) (courts may not “simply ignore[] the
reality of the prison system”); Rivera v. Nolan, 538 F. Supp. 2d
429, 433 (D. Mass. 2008) (“Expectations about what defines due
diligence from behind prison bars must be realistic.”).

Simard

has submitted a declaration in which he offers reasons for any
alleged delay.

ECF No. 119-1.

The declaration focuses on his

federal litigation activity, the advice he received from counsel,
and impediments related to his incarceration.
Simard begins by noting that his attorneys challenged the
enhanced sentence in his federal case.

To the extent that such

challenges involved Simard’s direct appeal, that activity carries
no weight as Johnson held the duty of due diligence begins on the
date of final judgment.

544 U.S. at 297.

The Supreme Court thus

implicitly negated consideration of the defendant’s efforts in
connection with his federal appeal.

Simard also recalls counsel

initially informing him that it would be “very difficult or
impossible” to vacate his underlying state court conviction.

10

ECF

No. 119-1 at 1.
After his federal sentencing in August 2012, Simard was
allegedly assaulted at least five times and sexually assaulted
once while in prison.

He attributes his mistreatment to his

status as a person with a child pornography conviction.

Simard

also spent a significant amount of time in the special housing
unit (SHU).

Id. at 2 (“more than a year in the SHU

cumulatively”).

He was moved approximately 13 times, and during

one such move his legal papers were lost.

When he requested

legal help from prison staff, they referred him to inmates in the
law library.

Simard was reluctant to ask fellow inmates for

legal assistance because of the nature of his state and federal
convictions.
In “mid-to-late 2015” Simard reportedly learned from his
federal attorney that it might be possible to challenge his state
court conviction.

Id.

Federal counsel contacted the Vermont

Defender General’s office, but Simard himself had difficulty
communicating with state counsel in part because that office does
not accept collect calls.

Simard was not working at the time,

and explains that he had difficulty obtaining stamps from prison
staff.

Id.

He was ultimately able to challenge his state court

conviction, through counsel, in early 2016.
Given the substantial uncertainties in Vermont law at the
time of his federal sentencing, and the conditions specific to

11

Simard while incarcerated, the Court finds that he acted with due
diligence in pursuing post-conviction relief in state court.

He

is therefore entitled to relief under 28 U.S.C. § 2255, and the
Court will set a date for his re-sentencing.
Conclusion
For the reasons set forth above, the Court does not accept
the Magistrate Judge’s Report and Recommendation (ECF No. 120),
and instead grants Simard’s motion for habeas corpus relief, and
specifically re-sentencing (ECF No. 107), filed pursuant to 28
U.S.C. § 2255.
DATED at Burlington, in the District of Vermont, this 5th
day of November, 2019.
/s/ William K. Sessions III
William K. Sessions III
District Court Judge

12