In the
United States Court of Appeals
For the Seventh Circuit
No. 09-1443
U NITED S TATES OF A MERICA,
Plaintiff-Appellee,
v.
K ERRY L. S MITH,
Defendant-Appellant.
Appeal from the United States District Court
for the Southern District of Illinois.
No. 4:07-cr-40038-GPM-1—G. Patrick Murphy, Judge.
A RGUED JANUARY 19, 2010—D ECIDED A UGUST 19, 2010
BeforeB AUER and W OOD , Circuit Judges, and
K ENNELLY, District Judge.
K ENNELLY, District Judge. Kerry Smith pled guilty to
criminal charges pursuant to a written plea agreement
and was sentenced to a ninety-two month prison term.
He appeals, contending that the district court erroneously
The Honorable Matthew F. Kennelly, United States District
Court for the Northern District of Illinois, sitting by designation.
2 No. 09-1443
deprived him of his Sixth Amendment right to retain
the counsel of his choice. For the reasons stated below,
we vacate Smith’s conviction and remand with instruc-
tions to permit him to withdraw his guilty plea.
I. F ACTS
In April 2007, a grand jury indicted Kerry Smith on a
charge of conspiracy to distribute marijuana. Smith re-
tained attorney John Rogers to represent him. The
district court originally set the case for trial in mid-June
2007 but later continued the trial to September 2007.
In July 2007, the grand jury returned a superseding
indictment. The superseding indictment added charges
of money laundering, concealment of information from
the Social Security Administration, and making false
statements. The trial was continued, but the record does
not reflect that a new date was set.
Discovery in the case was voluminous. In March 2008,
Smith’s counsel Rogers filed a motion to suppress evi-
dence and a motion to sever charges. The case was put
on hold, however, after Rogers requested and the judge
ordered a competency evaluation of Smith. The evalua-
tion was completed in June 2008. The docket does not
reflect that a new trial date was set before or after the
completion of the evaluation.
On August 25, 2008, Smith filed a motion asking to
substitute a new retained attorney, Beau Brindley. The
motion cited Smith’s constitutional right to the counsel
No. 09-1443 3
of his choice. The record does not reflect that the court
had set a trial date at that point.
Smith’s motion to substitute counsel was called for
hearing on September 8, 2008. Prior to the hearing, there
was still no indication that the district court had set a
trial date. At the hearing, the district court first found
Smith competent to stand trial.
The court then turned to Smith’s motion to substitute
Brindley as his defense counsel. The court initially
stated that it was inclined to permit substitution of
counsel. It stated, however, that “the case is going to jury
trial November 4th. I’m going to pick a jury the Friday
before and if you are not ready you can’t substitute. So
it’s just that simple.” Sept. 8, 2008 Tr. 4. This was the
first time the court had made reference to a trial date,
and as we have noted the record contains no earlier men-
tion that the court had set the case for trial in Novem-
ber (or, for that matter, any other date). At oral argu-
ment before us, the government conceded that no trial
date had been set prior to the September 8, 2008 hearing
and that there had been no indication that the court
intended to try the case in November 2008.
After further discussion, the district court inquired
when Brindley had filed the proposed motion substitu-
tion of counsel. Brindley said he had filed the motion
several weeks earlier, and the court clerk reported that
the motion had been filed on August 25. The district
court then stated, “This matter has been set for some
time. Linda, announce the trial date.” The clerk stated,
“Jury selection November 3rd; trial will be November 4th
4 No. 09-1443
at 8:00 a.m.” 1 Id. at 6. Brindley told the court that he
was scheduled to be on trial in a multiple-defendant
racketeering conspiracy case from October 6 through
the beginning of December. The court then said, “You
don’t have any business in this case. You don’t have
time to do it.” Id. at 7.
The following colloquy ensued:
MR. BRINDLEY: Mr. Smith has a constitutional
right to choice of counsel.
THE COURT: No, he does not. He had a constitu-
tional right to counsel. He doesn’t
have a constitutional right to pick any
person he wanted. If that was the
case, we would have Brendan
Sullivan or Edward Bennett Wil-
liams or any number of attorneys.
You don’t necessarily get that.
MR. BRINDLEY: He gets—under the Constitution,
I believe, your Honor, he gets
whoever he can afford and is
willing to represent him.
THE COURT: But he doesn’t get his schedule.
And that’s what we’re talking
about here. Now, I’m telling you
that on November 4th on [sic] this
1
We note that the date the clerk announced for jury selection
was a Monday, not “the Friday before” the purported trial
date as the district court had earlier stated.
No. 09-1443 5
year, this case is going to trial.
Now if you tell me you can’t do
it, you can’t do it. But this case is
going to trial November 4th. It is
not a subject for discussion or a
topic up for debate. I have nothing
but matters set between now and
then. My schedule is what it is.
This is the time I’ve got to try the
case.
I’m going to let the three of you
discuss it and decide what you
are going to do. But your case
was already set in Chicago. You
are going to have to work around
that, or wherever it is.
Now, the Court’s in recess for
five minutes.
Id. Tr. 7-8 (emphasis added).
After the five minute recess, Smith’s original retained
counsel, Rogers, reported that Smith did not want
Rogers to continue to represent him. Rogers indicated
that Smith had been opposed to Rogers’ earlier request
for a competency examination and that their relation-
ship had deteriorated as a result. The court permitted
Rogers to withdraw and struck his appearance.
The court, addressing Smith, repeated that the case
was set for trial on November 4—less than two months
hence. The court told Smith that “[i]f your lawyer can
6 No. 09-1443
be here and represent you that is fine with the Court. If
he can’t, I will appoint a lawyer for you who will be
ready on November 4th. So it’s really up to Mr. Brindley
whether or not he is going to represent you in the mat-
ter.” Id. at 9. Brindley repeated that he had long been set
for trial in the other case and was therefore unavailable
on November 4.
The court denied Smith’s motion to substitute counsel
and stated, “[t]he Court will appoint counsel for the
defendant and you will hear from us shortly.” Id. at 10.
Smith then asked that his original attorney, Rogers,
continue to represent him, but the court denied Smith’s
request. The court also denied Smith’s request (through
Brindley) for a continuance. We quote the colloquy
from the hearing:
THE COURT: Mr. Smith . . . [d]o you have the
means and apparently enough
means to hire private coun-
sel. So if you—I will go ahead
and appoint you a lawyer for
November 4th and if you can
get someone down here of your
own choosing before then, that
will be fine.
MR. SMITH: If Mr. Brindley can’t defend me
I still want to go with Rogers
then.
THE COURT: Sometimes that— som etim es
that’s kind of like dating. Once
you get—once you get thrown
No. 09-1443 7
out the front door you might
not want to come in—
MR. SMITH: I just explained to both of them
a second ago. I mean, if he
couldn’t take over the case I—
THE COURT: Well, I’ll take another brief re-
cess. I’ll be out in five minutes.
I don’t know how Mr. Rogers
feels about that.
He doesn’t want to do it. He’s
out. That’s what I thought. So
that being the case, we’ll—
MR. BRINDLEY: Your Honor, just for the rec-
ord, for purposes of the record,
Mr. Smith would request a con-
tinuance so that I be allowed
to take the case since I am the
counsel of his preference.
THE COURT: There’s two things about that.
You’re not in this case.
MR. BRINDLEY: That I understand.
THE COURT: So I’ll talk to him about that.
Your motion to substitute is de-
nied.
MR. BRINDLEY: Would you inquire of Mr. Smith
then.
THE COURT: You are excused.
8 No. 09-1443
MR. BRINDLEY: Thank you, your Honor.
THE COURT: You are welcome.
Now, Mr. Smith. I assume that—
the Court doesn’t ordinarily get
involved in the financial situa-
tions, but I would think you have
a refund coming. If you want
to retain independent counsel
you can do that. In the mean-
time, I’m going to get appointed
counsel on your case and I urge
you to cooperate with this per-
son. November 4th what you
need to know and if you would
check with people that have
been in my court, this case is
going to trial. So just do the
best you can, I guess. You have
made—I think you have made
some decisions that you might
find questionable, but you will
get a fair trial. And if you can
get someone here quickly, the
Court would seriously consider
letting them substitute in.
Id. at 10-12.
Later that same date, the court entered an order ap-
pointing a new attorney, Ronald Jenkins, to represent
Smith. Jenkins first appeared before the court on Septem-
ber 12, 2008. He stated that he had first spoken to Smith
No. 09-1443 9
just before the hearing. Jenkins also indicated that he
would be ready to proceed on the trial date the court
had set.
On September 29, 2008, Smith entered a guilty plea to
all of the charges in the superseding indictment. This
was exactly three weeks after the court had denied
Smith’s request to allow Brindley to represent him,
and about two and one-half weeks after Jenkins first
appeared.
Smith pled guilty pursuant to a written plea agree-
ment. The plea agreement did not include any written
affirmation that Smith was acting voluntarily when he
signed the agreement. It did, however, include a state-
ment that Smith “is fully satisfied with the representa-
tion he has received from his counsel.” Plea Agr. ¶ III.1.
The plea agreement also included the following terms:
1. The Defendant understands that by pleading
guilty, he is waiving all appellate issues that might
have been available if he had exercised his right
to trial. . . .
2. The Defendant is aware that Title 18, Title 28, and
other provisions of the United States Code afford
every defendant limited rights to contest a convic-
tion and/or sentence. Acknowledging all this, and in
exchange for the recommendations and concessions
made by the Government in this plea agreement, the
Defendant knowingly and voluntarily waives his
right to contest any aspect of his conviction and sen-
tence that could be contested under Title 18 or
Title 28, or under any other provision of federal law,
10 No. 09-1443
except that if the sentence imposed is in excess of
the Sentencing Guidelines as determined by the
Court (or any applicable statutory minimum, which-
ever is greater), the Defendant reserves the right to
appeal the reasonableness of the sentence. . . .
3. Defendant’s waiver of his right to appeal or bring
collateral challenges shall not apply to: 1) any subse-
quent change in the interpretation of the law by the
United States Supreme Court or the United States
Court of Appeals for the Seventh Circuit, which is
declared retroactive by those Courts, and which
renders the Defendant actually innocent of the
charges covered herein, and 2) appeals based upon
Sentencing Guideline amendments which are made
retroactive by the United States Sentencing Com-
mission (see U.S.S.G. § 1B1.10). . . .
Plea Agr. ¶¶ III.1-3.
During the guilty plea colloquy, attorney Jenkins
stated that he had reviewed the file that he had
received from Smith’s prior counsel and had met with
Smith “for a significant period of time one day” to review
evidence. Sept. 29, 2008 Tr. 5. Jenkins stated that on the
Friday before the guilty plea hearing, he had a phone
call with Smith, who was in custody pending trial.
Jenkins had met with Smith again the morning of the
guilty plea.
After questioning Smith, the court found him com-
petent. The court elicited Smith’s agreement that he had,
in the court’s words, “plenty of time” to discuss the
case with Jenkins and that he was satisfied with Jenkins
No. 09-1443 11
as a lawyer. Id. at 7-8. The court ascertained that Smith
understood the rights he would give up by pleading
guilty. Id. at 8-10. After discussing the elements of the
offenses charged and the possible penalties, id. at 10-14 &
15-17, the court asked Smith whether anyone had threat-
ened or forced him to plead guilty, and Smith said no.
Id. at 14. This was the only reference to voluntariness; the
court did not ask Smith whether any promises had been
made to him and did not directly ask whether he was
acting voluntarily or of his free will. See Fed. R. Crim. P.
11(b)(2) (requiring court to “address the defendant per-
sonally in open court and determine that the plea is
voluntary and did not result from force, threats, or prom-
ises (other than promises in a plea agreement)).” There
was also a brief, though oblique, reference to the appel-
late waiver, which we will discuss shortly. Id. at 17. The
court elicited from Smith a statement that the matters
stated in a separately-filed stipulation of facts were true.
Id. at 18. After some further discussion, the court found
that Smith’s plea was knowing and voluntary. Id. at 20.
In February 2009, the district court imposed a prison
sentence of ninety-two months. Smith filed a notice of
appeal. The government moved to dismiss the appeal. We
consolidated the motion with argument on the merits
and directed the parties to address in their merits
briefs whether Smith’s guilty plea was voluntary.
III. D ISCUSSION
Smith contends that the district court violated his
Sixth Amendment right to counsel when it denied his
12 No. 09-1443
motion to substitute Brindley as trial counsel. Before
addressing the merits, we consider the government’s
contention that Smith waived his right to appeal.
A. Appellate Waiver
The government has not argued, either in its motion
to dismiss or in its brief, that simply by pleading guilty,
Smith waived any contention that the district court vio-
lated his Sixth Amendment rights. The point is thus
likely forfeited.
Forfeiture aside, any such contention would be lacking
in merit. It is true that an unconditional guilty plea typi-
cally waives non-jurisdictional defects in the pro-
ceedings below. See Tollett v. Henderson, 411 U.S. 258,
267 (1973). The Supreme Court has recently held, however,
that the erroneous deprivation of the right to counsel
of choice in violation of the Sixth Amendment is a “struc-
tural error” in a criminal proceeding and is not subject
to harmless error analysis. United States v. Gonzalez-Lopez,
548 U.S. 140, 150-52 (2006). The Court stated that
[d]ifferent attorneys will pursue different strategies.
And the choice of attorney will affect whether and
on what terms the defendant cooperates with the
prosecution, plea bargains, or decides instead to go
to trial. In light of these myriad aspects of representa-
tion, the erroneous denial of counsel bears directly
on the framework within which the trial proceeds,
or indeed on whether it proceeds at all. . . . Many
counseled decisions, including those involving plea
No. 09-1443 13
bargains and cooperation with the government, do not
even concern the conduct of the trial at all.
Id. at 150.
Relying on Gonzalez-Lopez, the Fifth Circuit recently
held that a defendant’s guilty plea does not preclude
him from challenging on appeal a denial of his right to
counsel of choice. United States v. Sanchez-Guerrero, 546
F.3d 328, 332 (5th Cir. 2008). We agree. As the Fifth
Circuit stated, “it is obvious that the choice of counsel
may seriously impact a defendant’s decision to plead
guilty.” Id. “If a defendant is erroneously denied the
counsel of his choice, it is a structural error in the trial
that brings into question the voluntary and intelligent
character of the guilty plea itself. ” Id. Under the circum-
stances, Smith’s guilty plea does not amount to a waiver
of his Sixth Amendment choice-of-counsel claim.
The government argues that Smith waived the right to
appeal via the appellate waiver in his plea agreement.
There is no question that a defendant may waive his
right to a direct appeal as part of a plea agreement. See, e.g.,
Jones v. United States, 167 F.3d 1142,1144 (7th Cir. 1999). But
appellate waivers are not blindly enforced. See, e.g., United
States v. Rhodes, 330 F.3d 949, 952 (7th Cir. 2003). “To
determine if a defendant knew and understood the plea
agreement, we must examine the language of the plea
agreement itself and also look to the plea colloquy
between the defendant and the judge.” United States
v. Chapa, 602 F.3d 865, 868 (7th Cir. 2010) (citing United
States v. Sura, 511 F.3d 654, 661 (7th Cir. 2007)).
14 No. 09-1443
The appellate waiver itself was reasonably clear. That,
however, is not the end of the inquiry. If it was, Rule
11(b)’s requirement that the district court address the
defendant personally would be a dead letter.
Turning to the district court’s colloquy with Smith
regarding the appellate waiver, we conclude that it fell
short of what the law requires. Federal Rule of Criminal
Procedure 11 was amended effective December 1, 1999
“to reflect the increasing practice of including provi-
sions in plea agreements which require the defendant to
waive certain appellate rights.” Fed. R. Crim. P. 11, 1999
advisory committee notes. The newly-added provision
states that the district court “must inform the defendant
of, and determine that the defendant understands . . .
the terms of any plea-agreement provision waiving the
right to appeal or to collaterally attack the sentence.”
Fed. R. Crim. P. 11(b)(1)(N).
The district court erred by failing during the plea col-
loquy to advise Smith of the terms of the appellate
waiver and determine whether he understood that pro-
vision. See Sura, 511 F.3d at 661-62. Smith did not argue
this omission before the district court, so we review the
point for plain error. United States v. Vonn, 535 U.S. 55, 59
(2002); Sura, 511 F.3d at 658. Specifically, Smith must
show that his substantial rights were affected and that
the error seriously affected the fairness, integrity, or
public reputation of the court proceeding. Vonn, 535 U.S.
at 62-63.
We conclude that Smith has made the necessary
showing. First, Smith’s substantial rights were affected;
No. 09-1443 15
the violation of his Sixth Amendment rights occurred and
was complete (as we will discuss) at the time the district
court denied his motion to substitute counsel. Second,
the error had a significant effect on the fairness of the
proceedings. The right to counsel is one of the bedrock
elements protecting the fairness of the adversary pro-
cess. See, e.g., Strickland v. Washington, 466 U.S. 668, 684
(1984). The Supreme Court made it clear in Gonzalez-
Lopez that “the right to select counsel of one’s choice . . .
has been regarded as the root meaning of the constitu-
tional guarantee” contained in the Sixth Amendment.
Gonzalez-Lopez, 548 U.S. at 147-48.
We therefore consider whether the trial court com-
plied with Rule 11(b)(1)(N)’s requirements. During the
course of the guilty plea colloquy, the court did not
explain, quote, or even summarize the appellate waiver
to Smith. Nor did it elicit from Smith a statement that
reasonably can be construed as indicating awareness
that he was giving up his right to appeal from rulings
the court had previously made. Rather, the court
referred to the plea agreement’s appellate waiver only
obliquely, and in a brief question not to Smith himself,
but to the attorney the court had appointed to represent
him:
THE COURT: Now not having read all of this
agreement is there a—is there an
appeal waiver in here?
MR. JENKINS: Yes, sir.
THE COURT: And the terms of that waiver are
what?
16 No. 09-1443
MR. JENKINS: Basically, your Honor, that every-
thing is waived with the exception of
the reasonableness of the sentence.
THE COURT: All right.
MR. JENKINS: And he can’t withdraw his plea.
THE COURT: You understand that?
MR. SMITH: Yes, your Honor.
Sept. 29, 2008 Tr. 17.
This was inadequate, and it did not comport with
the requirements of Rule 11(b)(1)(N). All that was
stated in the record—by counsel, not the court—was
that “everything is waived with the exception of the
reasonableness of the sentence,” and that Smith “can’t
withdraw his plea.” The district court, which based on
its own comments apparently had not reviewed the
terms of the appellate waiver, did not explain the sub-
stance of the waiver to Smith, as Rule 11(b)(1)(N) requires.
The Rule does not require a detailed description—
a statement that made it clear Smith was giving up any
right he might have to appeal decisions the court had
made, his conviction, and his sentence would have
sufficed—but the court gave Smith no explanation at all.
The court’s failure to provide Smith any explanation or
description of the appellate waiver was not cured by its
vague question to Smith, “You understand that?” “That”
is most reasonably understood as referring to what
Smith’s counsel had just said—that Smith had agreed
he “can’t withdraw his plea.” We cannot reasonably
No. 09-1443 17
conclude from this brief exchange that Smith under-
stood, or even said he understood, the appellate waiver.
Not every deviation from Rule 11(b)’s requirements
renders an appellate waiver unenforceable. In this case,
however, the record of the plea colloquy does not
reflect that Smith understood the appellate rights he
was giving up. More to the point, the record does not
reflect an understanding that Smith was giving up his
right to appeal from the district court’s denial of his
defense counsel of choice. Given the court’s failure to
meet the requirements of Rule 11(b)(1)(N) and the funda-
mental nature of the underlying right at issue, the
plea agreement’s appellate waiver does not preclude
Smith from challenging on direct appeal the court’s
alleged denial of his right to counsel of his choice.
B. Denial of Choice of Counsel
Turning to the merits, we conclude that Smith was
denied his Sixth Amendment right to his choice of coun-
sel. The Sixth Amendment “guarantees a defendant the
right to be represented by an otherwise qualified attorney
whom that defendant can afford to hire . . . .” Caplin &
Drysdale, Chartered v. United States, 491 U.S. 617, 624 (1989).
The constitution “commands . . . that the accused be
defended by the counsel he believes to be the best.”
Gonzalez-Lopez, 548 U.S. at 146.
This right, of course, is not without limits. Among
other things, trial courts have the authority to establish
criteria for admitting lawyers to practice, and a defendant
18 No. 09-1443
may not demand that a court honor his waiver of conflict-
free representation. See id. at 151-52 (citing Wheat v. United
States, 486 U.S. 153, 159-60 (1988)). Courts also have
an interest in ensuring that trials “are conducted within
the ethical standards of the profession and that legal
proceedings appear fair to all who observe them.” Wheat,
486 U.S. at 160 (quoted in Gonzalez-Lopez, 548 U.S. at 152)).
More directly pertinent to Smith’s case, the Supreme
Court has “recognized a trial court’s wide latitude in
balancing the right to counsel of choice against the needs
of fairness and against the demands of its calendar.”
Gonzalez-Lopez, 548 U.S. at 152 (citations omitted).
The record in this case, however, does not support a
contention that the demands of the district court’s
calendar justified denying Smith’s request to have
Brindley represent him. The district court based its
ruling entirely on its determination to try the case on
November 4, 2008, a date on which Brindley was unavail-
able due to a previously-set trial date in another court.
But the record reflects that the court had not set a Novem-
ber 4 trial date, or for that matter any trial date, prior
to Brindley’s appearance in court on the motion to sub-
stitute. The trial date was not set until the date
Brindley appeared—after the motion to substitute his
appearance had been on file for two weeks. (As we
have indicated, the government stated at oral argu-
ment before us that prior to the hearing on the motion
to substitute, no trial date had been set.)
We also note that based on the record, there is some
question whether the district court correctly understood
No. 09-1443 19
the scope of Smith’s right to counsel of his choice. As
quoted earlier, after Brindley argued that “Mr. Smith
has a constitutional right to choice of counsel,” the court
replied, “No, he does not. He had a constitutional right
to counsel. He doesn’t have a constitutional right to
pick any person he wanted.” Sept. 8, 2008 Tr. 7. That
statement is inconsistent with Gonzalez-Lopez and its
Supreme Court forebears. Though the court followed
this with a statement alluding to the court’s schedule
and counsel’s availability, the court’s comments, taken
as a whole, reflect that it did not give sufficient consider-
ation to Smith’s Sixth Amendment right to retain the
counsel of his choice.
The record also makes clear that the district court was
unwilling to entertain any sort of a continuance at all.
Specifically, the court stated that “this case is going to
trial November 4th. It is not a subject for discussion or
a topic up for debate.” Sept. 8, 2008 Tr. 8. When
Brindley attempted to bring up the topic again, the
court declined to consider it, saying that “[y]ou’re not
in this case” and that “I’ll talk to him [Smith] about that.”
Id. at 11. But when Brindley followed up by asking the
court to inquire of Smith, the court did not do so,
telling Brindley, “You are excused.” Id.
Adherence to a trial date once set is a worthy goal, but
a district court’s schedule, though a significant consider-
ation, does not automatically trump all other interests.
See United States v. Miller, 327 F.3d 598, 601 (7th Cir.
2003). In this case, no trial date had been set prior to
Brindley’s appearance on the motion to substitute. For
20 No. 09-1443
this reason, allowing him to substitute as Smith’s
counsel would not have adversely impacted any date
the court had previously set. The court’s desire to try
the case on November 4 does not justify its denial of
Smith’s right to counsel of his choice.
We also reject the government’s argument that Smith
was trying to manipulate the schedule by seeking to
substitute Brindley’s appearance. This argument lacks
any support in the record. Again, no trial date had been
set prior to the hearing on the motion to substitute. As
a result, there is no basis to conclude that Smith was
trying to stall the disposition of the case.
We find that the district court erroneously denied
Smith his constitutional right to his choice of defense
counsel. Under Gonzalez-Lopez, Smith is not required to
prove that he was prejudiced by the violation. 2 He is
entitled to have his guilty plea vacated.
III. C ONCLUSION
For the foregoing reasons, we vacate Smith’s conviction
and sentence and remand his case to the district court
2
Although a defendant who has been improperly denied the
counsel of his choice need not show prejudice, we note that
Smith pled guilty (in a case that had been pending for
nearly eighteen months) a mere three weeks after Brindley
was denied permission to substitute, Smith’s ensuing request
to reinstate his original attorney was overruled, and appointed
counsel was forced upon him.
No. 09-1443 21
with instructions to permit Smith to withdraw his guilty
plea. The government’s motion to dismiss the appeal
is denied. Circuit Rule 36 shall apply on remand.
8-19-10