                           In the

United States Court of Appeals
              For the Seventh Circuit

No. 08-3381

U NITED S TATES OF A MERICA,
                                              Plaintiff-Appellee,
                               v.

JEFFRY P OLAK,
                                          Defendant-Appellant.


          Appeal from the United States District Court
              for the Eastern District of Wisconsin.
         No. 08 CR 140—Rudolph T. Randa, Chief Judge.



     A RGUED F EBRUARY 25, 2009—D ECIDED JULY 20, 2009




 Before F LAUM, W ILLIAMS, and T INDER, Circuit Judges.
  W ILLIAMS, 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 circum-
stances shows that Polak’s acceptance of the plea agree-
ment, 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 fifty-
two 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, ascer-
tained that his attorney had reviewed the plea agree-
ment with him, questioned whether he was pleading
guilty voluntarily, asked if he was happy with the assis-
tance 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 sen-
tenced Polak to a “technically” above-Guidelines sentence
4                                                No. 08-3381

of a year and a day.1 The court noted that it declined to
adopt the Government’s recommendation because,
among other things: (1) probation would not be an ade-
quate 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,


1
   Although “technically” above the Guidelines range, Polak’s
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).
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 com-
mitted 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 accep-
tance 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 dif-
ference 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 defen-
dant’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 circum-
stances 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 agree-
ment 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 well-
advised 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 require-
ments, this type of appeal could be avoided in the future.


                  III. CONCLUSION
 For the foregoing reasons, Polak’s sentence is A FFIRMED.




                          7-20-09
