The Honorable Matthew F. Kennelly, United States District



Court for the Northern District of Illinois, sitting by designation.

In the

United States Court of Appeals

For the Seventh Circuit

No. 09-1443

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

KERRY L. SMITH,

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.

ARGUED JANUARY 19, 2010—DECIDED AUGUST 19, 2010

Before BAUER and WOOD, Circuit Judges, and

KENNELLY, District Judge.



KENNELLY, 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
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 instructions to permit him to withdraw his guilty plea.

I. FACTS

In April 2007, a grand jury indicted Kerry Smith on a

charge of conspiracy to distribute marijuana. Smith retained 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 evidence 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 evaluation 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 mention that the court had set the case for trial in November (or, for that matter, any other date). At oral argument 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 substitution 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

We note that the date the clerk announced for jury selection 1

was a Monday, not “the Friday before” the purported trial

date as the district court had earlier stated.

at 8:00 a.m.” Id. at 6. Brindley told the court that he 1

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 constitutional 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 Williams 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
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 relationship 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 matter.” 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 counsel. 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—sometimes

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 recess. 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 record, for purposes of the record,

Mr. Smith would request a continuance 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 denied.

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 situations, but I would think you have

a refund coming. If you want

to retain independent counsel

you can do that. In the meantime, I’m going to get appointed

counsel on your case and I urge

you to cooperate with this person. 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 appointing a new attorney, Ronald Jenkins, to represent

Smith. Jenkins first appeared before the court on September 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 agreement. The plea agreement did not include any written

affirmation that Smith was acting voluntarily when he

signed the agreement. It did, however, include a statement that Smith “is fully satisfied with the representation 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 conviction 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 sentence 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, whichever 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 subsequent 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 Commission (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 competent. 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 threatened 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 personally in open court and determine that the plea is

voluntary and did not result from force, threats, or promises (other than promises in a plea agreement)).” There

was also a brief, though oblique, reference to the appellate 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. DISCUSSION

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 violated 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 typically waives non-jurisdictional defects in the proceedings 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 “structural 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 representation, 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 circumstances, 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 provisions 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 colloquy to advise Smith of the terms of the appellate

waiver and determine whether he understood that provision. 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 process. See, e.g., Strickland v. Washington, 466 U.S. 668, 684

(1984). The Supreme Court made it clear in GonzalezLopez that “the right to select counsel of one’s choice . . .

has been regarded as the root meaning of the constitutional guarantee” contained in the Sixth Amendment.

Gonzalez-Lopez, 548 U.S. at 147-48.

We therefore consider whether the trial court complied 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 everything 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 substance 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 understood, 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 fundamental 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 counsel. 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 conflictfree 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 unavailable due to a previously-set trial date in another court.

But the record reflects that the court had not set a November 4 trial date, or for that matter any trial date, prior

to Brindley’s appearance in court on the motion to substitute. 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 argument 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 consideration 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 consideration, 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

Although a defendant who has been improperly denied the 2

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.

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. He is 2

entitled to have his guilty plea vacated.

III. CONCLUSION

For the foregoing reasons, we vacate Smith’s conviction

and sentence and remand his case to the district court
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