Denny Anderson v. USA
Filed opinion of the court by Judge Wood. This record does not permit us to decide once and for all whether Anderson had the capacity to be sentenced and to enter a knowing and voluntary plea. We REMAND so that Anderson can explore these issues in an evidentiary hearing. Diane P. Wood, Chief Judge; Ilana Diamond Rovner, Circuit Judge and David F. Hamilton, Circuit Judge. [6858362-1]  [15-2683]
United States Court of Appeals
For the Seventh Circuit
DENNY RAY ANDERSON,
UNITED STATES OF AMERICA,
Appeal from the United States District Court for the
Southern District of Indiana, Indianapolis Division.
No. 1:13‐cv‐01734‐TWP‐MJD — Tanya Walton Pratt, Judge.
ARGUED JANUARY 10, 2017 — DECIDED AUGUST 2, 2017
Before WOOD, Chief Judge, and ROVNER and HAMILTON,
WOOD, Chief Judge. At the time Denny Ray Anderson
pleaded guilty to being a felon in possession of a firearm, the
district court had only a general knowledge of Anderson’s
mental‐health problems. The court knew that Anderson had
been diagnosed as a paranoid schizophrenic and that he was
on psychotropic medication. But it did not know what other
illnesses Anderson had, what medication he had been pre‐
scribed, and how the drugs affected his functioning. The court
also was unaware that Anderson had only spotty access to his
medication while in jail awaiting trial. His appointed counsel,
who had observed Anderson behaving unusually at points
since his detention began, never requested a competence eval‐
uation or hearing.
Anderson’s plea agreement prevented him from directly
appealing his conviction and sentence, but he was nonethe‐
less entitled to file a motion for collateral relief under
28 U.S.C. § 2255. He did so, supporting his motion with two
arguments: first, that he was not competent at the time of his
guilty plea because of his illnesses and the effects of the med‐
ications he was taking; and second, that his attorney provided
constitutionally defective assistance for failing to challenge
his competence. The district court rejected his petition out‐
right. On appeal, he requests an evidentiary hearing to de‐
velop facts related to these interrelated claims. We agree that
a hearing is appropriate.
Anderson’s mental health was a recurring theme in the un‐
derlying offense for which he now seeks relief under section
2255. He was indicted on October 19, 2011, for being a felon
in possession of a firearm, in violation of 18 U.S.C. §§ 922(g)(1)
and 924(e), a charge to which he ultimately pleaded guilty. At
the government’s request, he was held in Indiana’s Marion
County Jail pending trial. Although the court had appointed
Anderson counsel, he still filed several pro se motions. In one,
he asked the court to dismiss his attorney because his attorney
was “not getting medical [r]ecords.” Anderson also alleged
that his appointed lawyer had violated his constitutional
rights by seeking a continuance. His counsel resisted the re‐
quest to withdraw, but Anderson told the court that he would
rather represent himself than have this lawyer remain on the
After a hearing in February 2012, the court decided to
grant Anderson’s request for a new lawyer. It appointed attor‐
ney Jesse A. Cook to replace the first lawyer. About six
months later, on August 16, 2012, Anderson filed with Cook’s
assistance a petition to enter a guilty plea. At the same time,
the parties submitted a written agreement that provided An‐
derson would plead guilty in return for a sentence of 15 years’
imprisonment. In the deal, Anderson expressly waived his
right to bring a direct appeal from the conviction and sen‐
tence. He did not waive his right to file any kind of collateral
The district court held a change of plea hearing on August
27, 2012. At the start of the proceeding, the court called
Anderson and Cook to the lectern. The transcript reveals
that Anderson started to approach the podium but apparently
changed course. The court summoned him again: “Come
right here. Where are you going, Mr. Anderson?” Anderson
said nothing, but the government’s attorney remarked:
“Ready to run around for a while.” The court then told
Anderson, “You have to stay in here.” That ended the episode,
and the court proceeded to obtain Anderson’s plea.
Later in the hearing, the district court asked about
Anderson’s mental health:
Court: Have you been treated recently for any
mental illness or addictions to alcohol or nar‐
cotic drugs of any kind?
Anderson: I’m on psychotropic drugs right now.
Court: Okay. What’s your diagnosis?
Anderson: Paranoid schizophrenia and a few
other things. I don’t know exactly everything.
Court: So, are you currently under the influence
of any drugs or medication?
Court: Okay. Does your medication affect your
ability to understand today’s proceedings?
Anderson: Not that I know of, Your Honor.
Court: Okay. So, right now you’re thinking
clearly and you understand what’s going on?
Anderson: Right. I mean, as good as I can, yeah.
The court did not press Anderson to explain what he un‐
derstood (and what he did not), nor did it ask what medica‐
tion he was taking. Instead, it continued the colloquy with
questions about his familiarity with the charge and his
knowledge of his legal rights. Anderson acknowledged
speaking with his attorney and said that he was pleased with
her advocacy on his behalf—a marked contrast from his dis‐
satisfaction with his first lawyer.
The court then proceeded to obtain Anderson’s guilty
plea. In response to the court’s questions, Anderson said that
he was pleading guilty of his own free will and that he was,
indeed, guilty. The following exchange then happened:
Court: … Mr. Anderson, do you understand
that the offense to which you are pleading
guilty, because it’s a felony offense, if the plea is
accepted, you will be adjudged guilty of that of‐
fense, and this adjudication may deprive you of
valuable civil rights, such as the right to vote,
the right to hold public office, the right to serve
on the jury, and the right to possess any kind of
firearm. Do you understand?
Court: Okay. Knowing—
Anderson: That’s pretty good.
Court: I’m sorry?
Anderson: That’s pretty good.
Court: Knowing all of these factors, do you still
wish to enter this plea of guilty?
Anderson’s peculiar statement (“That’s pretty good”) went
unexamined; instead, the district court proceeded with the
colloquy. In response to all of the remaining questions,
Anderson gave one‐ or two‐word answers, and those answers
were uniformly affirmative. At the end, the court accepted
Anderson’s guilty plea, finding that Anderson was “fully
competent and capable of entering an informed plea,” that he
knew about the nature of the charge and consequences of the
plea, and that his plea was “knowing and voluntary.”
The presentence investigation report (PSR) prepared for
the November 1, 2012 sentencing hearing noted that
Anderson said that he had been diagnosed with a host of
psychological disorders, including, but not limited to, bipolar
disorder, schizophrenia, chronic depression, and attention
deficit disorder. It reported that his medication regimen
included Thorazine (an antipsychotic medication used to
treat schizophrenia and manic‐depressive disorder), Artane
(a drug used to treat symptoms of Parkinson’s disease;
Anderson said that the drug had been prescribed to treat side
effects of his other medication), Tegretol (a prescription used
to prevent and control seizures which is sometimes used to
treat bipolar disorder and schizophrenia), and Ritalin. The
PSR also noted that the probation office had not reviewed all
of Anderson’s recent records because his health care provider
in early 2011—whom Anderson saw after he was released
from prison in connection with an earlier offense—had not
responded to the office’s request. Anderson had told the
probation office that despite his best efforts he had been
unable to obtain his medication since he was released earlier
that year, but that he had been thinking “more clearly” since
he began receiving medication at the jail.
The topics of Anderson’s mental health and medication
came up numerous times during sentencing. First, all parties
agreed that Anderson had not been taking his prescriptions at
the time of the offense, and his lack of medication was cited
as a factor in both the current offense and his earlier ones.
Second, in discussing one of his objections to the PSR’s
characterizations of his priors, Anderson defended to the
court his three thefts from Meijer stores on a peculiar ground.
He suggested that they were justified because the store had
fired him after he was in a car accident and was thus unable
to perform his job up to the store’s standards. The district
court admonished him that stealing was “still a bad thing to
do” and against the law. Anderson noted that it was “only a
[class] D felony.” Third, defense counsel Cook argued that
Anderson’s difficulty in obtaining medication justified a
sentence below the guidelines range, as called for in the plea
deal. The prosecution similarly cited Anderson’s mental‐
health troubles in asking for the agreed‐upon sentence.
Finally, Cook reported that she had seen Anderson’s be‐
havior fluctuate over the course of her representation of him.
Cook attributed this to the jail’s inconsistent delivery of his
medication. Each time Anderson was moved to a different
cellblock, a period would follow in which Anderson would
not receive the “right medication,” as she described it. Cook
said it was “pretty clear” that when Anderson “[is] not medi‐
cated, he has an extremely difficult time conforming his be‐
havior to what … the Court would expect.” And so Cook sent
the court the “full list” of Anderson’s prescribed medications
(and a medical record listing his “primary diagnosis” as schiz‐
ophrenia) with the hope that the information would get con‐
veyed to the Bureau of Prisons. Anderson reiterated his con‐
cern about sporadic access to his medications immediately af‐
ter the court announced his sentence: “[I]t’s just one day[,]
they will give me part of it …. And then the next time I might
not get it at all. Like, this morning, they came to give me my
meds, and they didn’t have all my meds for me.” In turn, the
court ordered the probation office to report to someone (un‐
clear to whom) that Anderson was having problem getting his
None of this information precipitated a pause in the
sentencing hearing, despite its troubling implications for
Anderson’s competence. Noting that it previously had
found Anderson “fully competent and capable of entering an
informed plea,” the court sentenced Anderson to 180 months’
imprisonment—the statutory minimum, given Anderson’s
criminal history, and eight months less than the low end of his
sentencing guidelines range of 188 to 235 months.
On October 28, 2013, Anderson filed a motion under
section 2255 seeking an evidentiary hearing, the appointment
of counsel, and relief from his conviction and sentence. His
motion alleged in relevant part that: (1) his plea had not been
knowing, intelligent, and voluntary, because of his mental
illnesses and medication, and (2) his counsel provided
ineffective assistance for failing to raise a capacity claim.
The district court denied his motion without an eviden‐
tiary hearing. It noted that Anderson repeatedly had told the
court that he was entering a knowing and voluntary plea. The
court continued that it was “well aware” of Anderson’s men‐
tal health problems, and that it believed that Anderson was
able to consult with his lawyer “with a reasonable degree of
rational understanding.” It concluded that there was no need
for an evidentiary hearing because Anderson had not alleged
facts that, if true, would entitle him to relief.
We granted Anderson a certificate of appealability on
May 13, 2016, on the question whether he was denied his right
to plead guilty competently and intelligently, and we re‐
cruited current counsel (for whose efforts we are grateful) to
represent him. On September 1, 2016, in response to a motion
from Anderson, we expanded the certificate to include inef‐
fective assistance of counsel.
On appeal, Anderson stresses his request for an eviden‐
tiary hearing to develop facts regarding his capacity to plead
guilty and be sentenced, as well as his contention that trial
counsel was constitutionally ineffective for failing to request
a competence evaluation or hearing. He appears to concede
that outright relief on the merits would be premature.
A district court should hold such an evidentiary hearing
whenever the federal prisoner alleges facts that, if proven,
would entitle him to relief. Torres‐Chavez v. United States,
828 F.3d 582, 586 (7th Cir. 2016); see also 28 U.S.C. § 2255. The
petitioner’s burden for receiving a hearing is “relatively
light.” Torres‐Chavez, 828 F.3d at 586. The district court should
deny an evidentiary hearing only when the motion and rec‐
ords “conclusively show” that the petitioner is not entitled to
relief. 28 U.S.C. § 2255(b). If the court decides that no hearing
is necessary, we review that determination only for an abuse
of discretion. Boulb v. United States, 818 F.3d 334, 339 (7th Cir.
Because Anderson’s capacity to plead guilty undergirds
his ineffective assistance of counsel claim, we begin with the
former. Due process prohibits the trial of a defendant who
lacks mental competence. Drope v. Missouri, 420 U.S. 162, 171–
72 (1975). This requirement, at its core, preserves the right to
a fair trial. See id. at 172. A defendant must have “sufficient
present ability to consult with his lawyer with a reasonable
degree of rational understanding” and have “a rational as
well as factual understanding of the proceedings against
him.” Dusky v. United States, 362 U.S. 402, 402 (1960) (per cu‐
riam) (quotation marks omitted); accord Drope, 420 U.S.
at 172. The competence requirement is not limited to defend‐
ants who proceed to trial; it also protects those, like Anderson,
who enter pleas. Godinez v. Moran, 509 U.S. 389, 391, 398
(1993). Nor is competence irrelevant after the guilt phase of a
criminal case—it applies to sentencing proceedings as well.
United States v. Garrett, 903 F.2d 1105, 1115 (7th Cir. 1990). In
addition to finding that the defendant satisfies this threshold
level of competence, the trial court also must ensure that the
defendant is pleading guilty knowingly and voluntarily. See
Godinez, 509 U.S. at 400–01 & n.12. This companion require‐
ment ensures that the defendant “understand[s] the signifi‐
cance and consequences of a particular decision” and that his
decision is not coerced. Id. at 401 n.12.
We begin with the obvious: Anderson suffered from a se‐
vere psychotic disorder. At the time of the change‐of‐plea
hearing, the district court knew that Anderson was a paranoid
schizophrenic, and that he had been diagnosed with that and
“a few other things.” Anderson’s disclosure should have
alerted the court to the possibility of a competence issue, even
if his medical history standing alone did not trigger the need
for an evaluation. See United States v. Morgano, 39 F.3d 1358,
1374 (7th Cir. 1994) (district court properly focused compe‐
tence inquiry on defendant’s mental state at the time, rather
than decades‐old medical history). Persons in the criminal jus‐
tice system often have diagnosed mental illnesses. See, e.g.,
Jennifer Bronson & Marcus Berzofsky, Indicators of Mental
Health Problems Reported by Prisoners and Jail Inmates, 2011–12,
U.S. DEP’T OF JUSTICE, BUREAU OF JUSTICE STATISTICS
(June 2017), www.bjs.gov/content/pub/pdf/imhprpji1112.pdf
(last visited Aug. 2, 2017) (more than one third of federal pris‐
oners reported being told they had a mental health disorder);
see also Eddmonds v. Peters, 93 F.3d 1307, 1315 (7th Cir. 1996)
(noting the Constitution “does not necessarily forbid trial of
the mentally ill”). The court did not inquire about Anderson’s
“other things,” but moved directly into the remainder of the
inquiry prescribed by Federal Rule of Criminal Procedure 11.
The need for a more probing inquiry became apparent—
indeed, pressing—when Anderson disclosed his use of un‐
specified psychotropic drugs. A defendant’s use of such po‐
tent medications can, by itself, create a “substantial doubt”
about a defendant’s fitness to plead guilty. McManus v. Neal,
779 F.3d 634, 639 (7th Cir. 2015). Here, that concern was am‐
plified by the dearth of information regarding exactly what
drugs Anderson was on, and how they affected his cogni‐
tion—matters the court left unexplored. See Burt v. Uchtman,
422 F.3d 557, 566 (7th Cir. 2005) (the court’s knowledge that
defendant is on psychotropic drugs, but lack of knowledge
about what drugs those were, weighs heavily in favor of the
need for a competency hearing). Anderson’s belief about the
effects of his medication is inadequate assurance that he was
capable of entering a plea: A person grappling with a serious
mental illness or under the influence of psychotropic drugs
cannot be assumed to have a reliable understanding of his fac‐
ulties. Worse, Anderson acknowledged some inability to think
clearly and participate in the proceedings when he told the
court that he understood what was going on “as good as I
Because the district court lacked a full picture of
Anderson’s mental health, its finding that Anderson had the
capacity to plead guilty rests on a flawed factual foundation
that must be explored in a hearing. To begin with, the court
should have ascertained what medication Anderson was on
and how it affected his thinking before proceeding to accept
his guilty plea. Had it done so, it probably would have
learned that he received his medication irregularly during his
pretrial detention—a fact that defense counsel apparently
knew, but which she disclosed only at sentencing. Once the
court had this information, it then could have made an
informed decision about the need for a competence hearing
or a psychiatric evaluation. See 18 U.S.C. § 4241; United States
v. Weathington, 507 F.3d 1068, 1073–74 (7th Cir. 2007).
The same problem taints Anderson’s sentencing hearing.
By this time, the court knew more: the PSR informed it about
Anderson’s multiple mental illnesses and the fact that his
medication regimen included the powerful antipsychotic pre‐
scription Thorazine. Yet it neither determined how the Thora‐
zine, along with his other medications, affected his function‐
ing, nor explained why it regarded this step as unnecessary.
On this record, we cannot be confident that Anderson was
competent at the time of his sentencing. Moreover, his earlier
statement that he was functioning much better now that he
was receiving medication from the jail was contradicted by
his attorney’s observation of his behavioral irregularities and
the fact that he was not receiving his medications on a regular
basis. All of this should have been explored in an evidentiary
Anderson also seeks an evidentiary hearing to develop his
ineffective assistance of counsel claim. He contends that his
lawyer rendered constitutionally inadequate assistance by
failing to request a competence evaluation or a hearing to de‐
termine if he was fit. This argument goes hand‐in‐hand with
his due process argument. We can be brief, since we already
have determined that a hearing is necessary.
The Sixth Amendment guarantees a criminal defendant
the right to be represented by effective counsel. Strickland v.
Washington, 466 U.S. 668, 686 (1984). A defendant claiming
that his defense counsel was inadequate must show both that
counsel’s performance was deficient, and that but for the de‐
ficient performance, there is a reasonable probability that the
outcome of the proceeding would have been different. Id. at
687–88, 693. Defense counsel performs deficiently when she
fails to “investigate possible defenses or make reasonable de‐
cisions that particular investigations are unnecessary.” Warren
v. Baenen, 712 F.3d 1090, 1100 (7th Cir. 2013) (quoting Burt,
422 F.3d at 566). When the defendant argues that counsel
should have pursued a fitness hearing, the question is
whether there is a “reasonable probability that the defendant
would have been found unfit had a hearing been held.” Id.
In conducting our Sixth Amendment inquiry, we apply a
“strong presumption that counsel’s conduct falls within the
wide range of reasonable professional assistance.” Swanson v.
United States, 692 F.3d 708, 714 (7th Cir. 2012). Nonetheless,
evidentiary hearings often are needed because ineffective as‐
sistance claims generally turn on facts outside the trial record.
Osagiede v. United States, 543 F.3d 399, 408 (7th Cir. 2008). For
instance, the record rarely will reveal whether counsel’s ac‐
tions were or were not considered, tactical choices. See Torres‐
Chavez, 828 F.3d at 586 (quoting Osagiede, 543 F.3d at 408).
Just as we have questions about Anderson’s capacity to
plead guilty, we have questions about Cook’s decision not to
raise Anderson’s capacity to the court. Cook knew that An‐
derson had a lengthy criminal record that had been fueled by
untreated mental illnesses. And Cook knew that the jail in‐
consistently gave Anderson his medication during his pretrial
detention, and that these gaps in treatment resulted in periods
of instability. This was enough to call into question Ander‐
son’s ability to consult with counsel and his understanding of
the proceeding. See Dusky, 362 U.S. at 402.
The government tries to bat away the need for a hearing
by focusing on Cook’s description of Anderson’s behavior
when he was medicated. True, a court generally is “entitled to
rely on representations from an attorney that h[er] client is
competent.” Chichalky v. United States, 926 F.2d 624, 634
(7th Cir. 1991). But that is only part of the story, and the less
important part. Cook never flatly stated that Anderson was
fit; she suggested that Anderson was fit sometimes. And Cook’s
apparent diligence in other aspects of her representation of
Anderson does not erase the importance of a full exploration
into Anderson’s competence. Because, in the words of section
2255(b), “the motion and the files and records of the case” do
not “conclusively show that the prisoner is entitled to no re‐
lief,” counsel should have pushed for a hearing.
Whether Anderson was prejudiced by that failure is a
question closely related to the merits of his capacity claim. If
the capacity claim founders, then Anderson may have a hard
time showing prejudice from his counsel’s decision to abstain
from exploring his capacity further.
This record does not permit us to decide once and for all
whether Anderson had the capacity to be sentenced and to
enter a knowing and voluntary plea. We REMAND so that An‐
derson can explore these issues in an evidentiary hearing.
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