In the

United States Court of Appeals

For the Seventh Circuit

No. 08-3381

UNITED STATES OF AMERICA,

Plaintiff-Appellee,

v.

JEFFRY POLAK, 

Defendant-Appellant.

Appeal from the United States District Court 

for the Eastern District of Wisconsin.

No. 08 CR 140—Rudolph T. Randa, Chief Judge.

ARGUED FEBRUARY 25, 2009—DECIDED JULY 20, 2009

Before FLAUM, WILLIAMS, and TINDER, Circuit Judges.

WILLIAMS, Circuit Judge. We are faced with an

appeal based on a sentencing court’s failure to fully

adhere to the requirements of Rule 11 of the Federal

Rules of Criminal Procedure. Jeffry Polak contends that

because the district court failed to inquire about his

knowledge of his plea agreement’s appellate waiver

before accepting his guilty plea, we must remand for

resentencing. Although the district court’s plea colloquy
2 No. 08-3381

was deficient, we find that the totality of the circumstances shows that Polak’s acceptance of the plea agreement, complete with appellate waiver, was knowing

and voluntary, so we affirm his sentence.

I. BACKGROUND

On April 4, 2008, Jeffry Polak, an honorably discharged

Marine Corps veteran, walked into Milwaukee’s Veterans

Affairs Medical Center and walked out with the VA’s fiftytwo inch flat screen television. The police apprehended

Polak, whose recent history had been marred by alcohol

abuse and a string of petty crimes. Polak immediately

confessed and agreed to plead guilty to a one-count

information in what the prosecutor described as the

quickest plea agreement in his career.

The plea agreement contained a standard appellate

waiver under which Polak agreed to waive all appellate

rights, including the right to contest his sentence. In

addition, among other safeguards, the agreement

required Polak to affirm that his “attorney ha[d] reviewed

every part of this agreement with me and ha[d] advised

me of the implications of the sentencing guidelines.”

During the plea colloquy, the district court reviewed the

rights that Polak was ceding by pleading guilty, ascertained that his attorney had reviewed the plea agreement with him, questioned whether he was pleading

guilty voluntarily, asked if he was happy with the assistance of his counsel, and discussed the maximum

penalties with him. Then, the court accepted his guilty

plea.
No. 08-3381 3

After the court took his plea, the following exchange

occurred:

Government: Your honor, sorry to interrupt. Before we

turn to scheduling matters, if I could just note

that there is an appeal waiver in this particular plea

Agreement at Paragraph 32.

The Court: Okay. Are you reminding me of the

mistake I made in the James Sura case?

Government: In Rule 11 as amended fairly recently it

would be appropriate to have a colloquy with the

Defendant about the appeal waiver paragraph.

The Court: All right. You know, I agree with

Judge Easterbrook in the dissent in that case. The

prosecutor has pointed out, Mr. Polak, that by signing

this Plea Agreement you have indicated here that

you’re waiving your right to appeal.

Polak: I’m aware of that your honor.

The Court: And you’ve gone over that with Mr. Stiller,

your Attorney?

Polak: Yes, I have, Your Honor.

At Polak’s sentencing hearing, the parties agreed that

the advisory Sentencing Guidelines range was six to

twelve months. The Government recommended that

Polak only receive three years’ probation in light of his

veteran status, his quick plea, and other mitigating

factors. Despite this recommendation, the court sentenced Polak to a “technically” above-Guidelines sentence
4 No. 08-3381

Although “technically” above the Guidelines range, Polak’s 1

sentence will likely be shorter than twelve months because

he will be eligible to receive a reduction for good behavior,

whereas if he received a lesser sentence he would not be

eligible for such a reduction. See 18 U.S.C. § 3624(b)(1).

of a year and a day. The court noted that it declined to 1

adopt the Government’s recommendation because,

among other things: (1) probation would not be an adequate deterrent to Polak; (2) Polak, a veteran, victimized

other veterans who were down on their luck; and

(3) Polak needed to receive alcohol treatment in a

custodial environment. 

II. ANALYSIS

A. The Totality of the Circumstances Shows that Polak’s

Guilty Plea Was Knowing and Voluntary

Polak argues that the district court violated Rule 11 of the

Federal Rules of Criminal Procedure when it failed to

ascertain Polak’s understanding of the appellate waiver

before accepting his plea, and that, as a result, we must

remand for resentencing. He also argues that the district

court erred when it failed to specifically mention,

during the plea colloquy, that the appellate waiver

applied to the court’s sentencing decision as well as to

the plea itself.

Rule 11, a “guilty-plea safeguard,” details the

procedures that a district court must follow when a

defendant wishes to plead guilty. United States v. Sura,
No. 08-3381 5

511 F.3d 654, 657 (7th Cir. 2007). It exists “to assist the

district judge in making the constitutionally required

determination that a defendant’s guilty plea is truly

voluntary . . . [and] to produce a complete record at the

time the plea is entered of the factors relevant to this

voluntariness determination.” Id. at 657 (quoting McCarthy

v. United States, 394 U.S. 459, 465 (1969)). So, “the more

meticulously the Rule is adhered to, the more it tends

to discourage, or at least to enable more expeditious

disposition of, the numerous and often frivolous . . . attacks

on the constitutional validity of guilty pleas.” Sura,

511 F.3d at 657-58 (quoting McCarthy, 394 U.S. at 465).

Rule 11(b)(1)(N) specifically requires a sentencing court

to review “the terms of any plea-agreement provision

waiving the right to appeal or to collaterally attack the

sentence” with the defendant before accepting his guilty

plea. Sura, 511 F.3d at 665 (7th Cir. 2007) (citing Fed. R.

Crim. P. 11(b)(1)(N)). So, here, the district court committed error when it failed to discuss the appellate

waiver provision before accepting Polak’s plea. Because

Polak failed to object before the end of the colloquy, our

examination here is whether this error was plain. Id. at 658.

In order for the district court’s error to be plain, we

must find that it: (1) affected Polak’s substantial rights; and

(2) seriously affected the fairness, integrity, or public

reputation of the judicial proceedings. United States v.

McMath, 559 F.3d 657, 667 (7th Cir. 2009) (citing Johnson v.

United States, 520 U.S. 461, 466-67 (1997)). It is Polak’s

burden to demonstrate that the district court’s failure to

abide by Rule 11 affected his substantial rights. United
6 No. 08-3381

States v. Olano, 507 U.S. 725, 734-35 (1993). We must look

to the totality of the circumstances surrounding the

negotiation of the plea agreement and the court’s acceptance of the plea to determine whether the district court’s

failure to properly inquire about the appellate waiver

during the plea colloquy constitutes plain error. Sura,

511 F.3d at 661. In doing so, the most important question

to ask is whether the plea was truly voluntary. Id. In

making this evaluation, we may examine evidence

outside the Rule 11 colloquy. United States v. Vonn, 535

U.S. 55, 74-75 (2002). It is a defendant’s burden to show

that his plea was not voluntary. Sura, 511 F.3d at 661. To

do so, he must “show a reasonable probability that, but

for the error, he would not have entered the plea.”

United States v. Dominguez Benitez, 542 U.S. 74, 76 (2004).

If “the safeguard required by Rule 11 is missing, the

record must reveal an adequate substitute for it, and the

defendant must show why the omission made a difference to him.” Sura, 511 F.3d at 667.

In Sura, although the district court asked whether the

defendant read his plea agreement and advised him that

he was relinquishing certain rights, it failed to inquire

about the defendant’s knowledge of an appellate waiver

during the plea colloquy. Id. at 656-57. We found that, in

the absence of a proper and complete Rule 11 colloquy,

the defendant’s plea was not knowing and voluntary.

Id. at 662-63. In determining this, we noted that: (1) the

plea colloquy not only failed to mention the appellate

waiver, but also failed to ascertain whether the defendant

went over the agreement with his attorney; (2) the defendant’s age, mental condition, and confused responses
No. 08-3381 7

to the court tended to indicate that he had not fully

understood the plea agreement; and (3) the record failed

to show any substitute that could replace the safeguards

of Rule 11. Id. at 662.

Unlike in Sura, the record in this case reveals that

Polak’s plea was voluntary and that substitutes for a

proper Rule 11 colloquy were in place, which indicated

that Polak was aware of the plea’s appellate waiver. In

Sura, we dealt with an unsophisticated defendant and the

record did not show that he had read and understood

the appellate waiver. Here, we deal with a more

educated defendant and the record reveals, in several

ways, that he had adequate knowledge of the appellate

waiver. Among other things: (1) the court inquired

about whether Polak had gone over the agreement with

his attorney, and Polak responded that he had;

(2) Polak signed the plea agreement below a statement

that stated that he reviewed all aspects of the plea with

his attorney; (3) the court inquired about his knowledge

of the appellate waiver, albeit after he entered the plea;

(4) Polak had a high school education and a career in

the military; and (5) the Government had overwhelming

evidence against Polak, making the acceptance of a plea

agreement (with appellate waiver) highly reasonable.

Perhaps most persuasive is the fact that Polak admits

that he still wants to plead guilty (he just wants to be

resentenced)—therefore, any argument that “but for

the error, he would not have entered the plea” must

be viewed with skepticism. See id. at 658. Based on

these factors, we find that the totality of the circumstances shows that Polak’s plea was voluntary, and we
8 No. 08-3381

therefore uphold his appellate waiver. Further, because

the plain text of the waiver indicates that the waiver

applied to both his plea and his sentence, and because

we held that there was adequate indicia in the record

that he had knowledge of the waiver, we reject Polak’s

argument that the district court committed plain error

when it did not specifically mention that the appellate

waiver applied to collateral attacks on his sentence.

Because the appellate waiver in Polak’s plea agreement is valid, we need not address Polak’s claim that

his sentence is unreasonable. We therefore affirm his

sentence.

Finally, we note that although harmless on this

record, these omissions are far from inconsequential and

entirely preventable. To prevent these occurrences in

the future, district court judges would be welladvised to follow the model for conducting a plea

colloquy outlined in the Benchbook for United

States District Court Judges. See § 2.01 (5th ed. 2007);

also available at http://cwn.fjc.dcn/public/pdf.nsf/lookup/

Benchbk5.pdf/$file/Benchbk5.pdf. We also note that it is

the responsibility not only of the district court, but also

of the prosecutor and defense counsel to ensure that a

plea meets the requirements of Rule 11. District court

judges are juggling hundreds of cases, both civil and

criminal. Mistakes happen, but if the court inadvertently

misses a step in the plea colloquy, counsel should speak up

and bring the omission to the court’s attention before the

plea is accepted. Busy trial judges will welcome the

opportunity to avoid error. If the court and both counsel
No. 08-3381 9

utilize a checklist which spells out the Rule 11 requirements, this type of appeal could be avoided in the future.

III. CONCLUSION

For the foregoing reasons, Polak’s sentence is AFFIRMED.

7-20-09