                             In the

    United States Court of Appeals
                For the Seventh Circuit
No. 12-1374

THOMAS H. HURLOW,
                                             Petitioner-Appellant,

                               v.


UNITED STATES OF AMERICA,
                                            Respondent-Appellee.


         Appeal from the United States District Court for the
          Southern District of Indiana, Terre Haute Division.
    No. 2:10-cv-00244-WTL-WGH — William T. Lawrence, Judge.




      ARGUED MAY 29, 2013 — DECIDED AUGUST 9, 2013




   Before BAUER, WOOD, and TINDER, Circuit Judges.

   BAUER, Circuit Judge. Petitioner Thomas Hurlow pleaded
guilty to multiple drug and firearm offenses after law enforce-
ment officials discovered drugs and a firearm in the home
Hurlow shared with his fiancée. In a written plea agreement,
2                                                   No. 12-1374

Hurlow waived his right to challenge his conviction under 28
U.S.C. § 2255. He has done just that, though, alleging in a
§ 2255 petition that he advised his trial counsel of events that
suggested that the search of his home was in violation of
Georgia v. Randolph, 547 U.S. 103 (2006), but that counsel failed
to investigate those events and instead persuaded Hurlow to
plead guilty. The district court denied Hurlow’s request for an
evidentiary hearing and concluded that his § 2255 motion was
barred by the waiver in his plea agreement. Because the § 2255
waiver in his plea agreement does not bar his claim that his
trial counsel was ineffective in negotiating the plea agreement,
we remand the matter to the district court for an evidentiary
hearing on that claim.
                     I. BACKGROUND
    On December 16, 2008, a case worker from the Indiana
Department of Child Services and two detectives from the Vigo
County Drug Task Force arrived at the home Hurlow shared
with his fiancée, Tina Funk, to conduct a welfare check on
Funk’s children. According to Hurlow, he objected to the
presence of the detectives and requested that they leave unless
they had a valid search warrant. The detectives instead asked
Funk for her permission to search the house. The detectives
told Funk that her children would be taken from her if she did
not agree to the search; Funk gave her written consent to the
search over Hurlow’s objections.
   During the search that followed, the detectives found a
substance containing detectable amounts of methamphet-
amine, marijuana, drug paraphernalia, and a handgun. After
being taken into custody and read his Miranda warnings,
No. 12-1374                                                    3

Hurlow told the detectives that all of the illegal items found
belonged to him and that Funk had no knowledge that the
drugs were in the home.
    According to Hurlow, he told his appointed trial counsel
the circumstances surrounding the search of the home that led
to his arrest. He also informed counsel that his “rights ha[d]
been violated” by the search and “requested that [counsel]
advocate that as a defense.” Hurlow contends, though, that
counsel “failed to listen to Hurlow’s version of events,”
“fail[ed] to investigate” the events surrounding the search, and
otherwise failed to make “any attempt” to pursue Hurlow’s
claim that the search was illegal. Instead, counsel persuaded
Hurlow to plead guilty to avoid a sentence of “30 years to life
imprisonment.”
   Based on counsel’s advice, Hurlow entered into a plea
agreement with the government and pleaded guilty to all of
the charges against him. Like many plea agreements, this one
contained a provision noting Hurlow’s agreement not to
contest his conviction or sentence in a collateral attack under
28 U.S.C. § 2255. In addition to the plea agreement, the parties
submitted a stipulated factual basis for the plea to the district
court. Regarding the December 2008 search that led to
Hurlow’s arrest, the document states that “Funk granted [the
detectives] consent to search [the home] in writing.”
    During his change of plea hearing on July 28, 2009, the
district court conducted a Rule 11 colloquy, and Hurlow
affirmed the factual basis for the plea, including that Funk
consented to the search. He also affirmed that he was satisfied
with his counsel’s representation and that he had “had
4                                                  No. 12-1374

sufficient time to talk with him and to work with him to try to
consider any options that [Hurlow] might have in this case[.]”
Hurlow agreed that there was not anything that he wanted his
counsel “to do in regards to this case that he failed to do[.]”
The district court concluded that Hurlow’s plea was “knowing
and voluntary,” and ultimately sentenced him to 248 months’
imprisonment.
    On September 9, 2010, Hurlow filed a motion for post-
conviction relief pursuant to 28 U.S.C. § 2255, arguing, among
other claims, that his plea agreement was involuntary because
it resulted from the ineffective assistance of trial counsel.
Hurlow alleged that he informed his trial counsel of the facts
surrounding the search of the home he shared with Funk but
that counsel failed to listen to Hurlow, conduct any investiga-
tion regarding the search, or file a motion to suppress that
would have been successful under Georgia v. Randolph. He
instead persuaded Hurlow to plead guilty.
    The district court rejected Hurlow’s request for an eviden-
tiary hearing and denied his § 2255 motion, concluding that
Hurlow had “waived his opportunity to challenge his convic-
tion pursuant to § 2255.” The district court reasoned that the
waiver in the plea agreement barred Hurlow’s motion because
Hurlow had not alleged that his counsel was “ineffective with
regard to negotiation of the waiver” and his statements at his
plea colloquy indicated that “his plea was knowing, intelligent,
and voluntary.” The district court accordingly denied
Hurlow’s § 2255 motion, denied a certificate of appealability,
and entered judgment on September 26, 2011.
No. 12-1374                                                            5

    On February 9, 2012, the district court docketed Hurlow’s
notice of appeal.1 Because the district court received the notice
of appeal outside the sixty-day window under Federal Rule of
Appellate Procedure 4(a)(1)(B), we ordered Hurlow to address
the timeliness of his appeal. In response, Hurlow filed declara-
tions asserting that he mailed his notice of appeal on
October 27, 2011, and seeks to avail himself of the prison
“mailbox rule.” See Fed. R. App. P. 4(c).
    According to Hurlow, on October 27, 2011, he prepared his
notice of appeal and request for a certificate of appealability,
placed the documents in a “postage pre-paid envelope,” and
deposited them in a mailbox located in his unit at Federal
Correctional Institution (F.C.I.) Williamsburg, the prison where
he was incarcerated. Hurlow says that “the [Federal Bureau of
Prisons] [has] a system for mailing letters certified,” and that
“the mailroom staff will document when [the mail was sent]
and to whom it is addressed,” but that he did not believe he
had to send his notice of appeal that way based on a conversa-
tion with the prison mailroom staff. Specifically, Hurlow
maintains that the “mailroom staff” told him that using the
mailbox in his unit “was just as efficient as placing [the
envelope] into their hands for first class mail,” that it “ma[de]
no difference” which method he chose, and that the envelope
“is considered delivered to the court the moment it is done.”


1
   It appears that Hurlow contacted this Court regarding his appeal at
some point, and when notified by a letter dated January 26, 2012, that he
did not have an appeal pending, sent the filing that was received on
February 9, 2012. The filing included copies of his notice of appeal and
request for a certificate of appealability dated October 27, 2011.
6                                                     No. 12-1374

    On October 31, 2012, we granted Hurlow’s request for a
certificate of appealability as to his claim that he was denied his
Sixth Amendment right to effective assistance of counsel in the
negotiation of his plea agreement.
                       II. DISCUSSION
    This appeal does not involve the merits of Hurlow’s
ineffective assistance of counsel claim. Rather, the appeal
presents us with two issues that go to whether Hurlow should
be heard on that claim: the timeliness of his appeal and the
effect of the § 2255 waiver in his plea agreement. We address
each in turn.
    A. Timeliness of Hurlow’s Appeal
    We first consider whether the prison mailbox rule applies
to Hurlow’s filing of his notice of appeal, thereby rendering it
timely. The prison mailbox rule, established by the Supreme
Court in Houston v. Lack, 487 U.S. 266, 275–76 (1988), and
codified in Rule 4(c) of the Federal Rules of Appellate Proce-
dure, provides that a prisoner’s notice of appeal is deemed
filed at the moment the prisoner places it in the prison mail
system, rather than when it reaches the court clerk. In order to
receive the benefit of the prison mailbox rule, Rule 4(c) requires
that an inmate use the prison’s legal mail system if it has one.
United States v. Craig, 368 F.3d 738, 740 (7th Cir. 2004) (citing
Fed. R. App. P. 4(c)(1)). If, however, “the prison lacks such a
system: ‘Timely filing may be shown by a declaration in
compliance with 28 U.S.C. § 1746 or by a notarized statement,
either of which must set forth the date of deposit and state that
first class postage has been prepaid.’” Id. (quoting Fed. R. App.
P. 4(c)(1)).
No. 12-1374                                                    7

    Here, in response to our request for briefing on the timeli-
ness of his appeal, Hurlow filed declarations stating that he
placed his notice of appeal in a postage pre-paid envelope in
his prison’s mail system on October 27, 2011, well within the
sixty-day window to appeal. The government contends that
Hurlow failed to comply with Rule 4(c), however, because
Hurlow’s statement that F.C.I. Williamsburg had a system for
sending certified mail affirmatively establishes that F.C.I.
Williamsburg had a system for legal mail, and Hurlow did not
use it. Alternatively, the government argues that Hurlow is not
entitled to the benefit of the prison mailbox rule because he has
not shown that F.C.I. Williamsburg did not have a legal mail
system at the time he mailed his notice of appeal.
    We find no merit to either argument. First, that the prison
had a system for sending and logging certified mail does not
mean it had a system “designed for legal mail.” See Fed. R.
App. P. 4(c). A “legal” mail system for purposes of Rule 4(c)(1),
is one that, at a minimum, is a “special” system separate from
the prison’s general mail system. See Ingram v. Jones, 507 F.3d
640, 644 (7th Cir. 2007) (noting that the prison had a “separate
legal mailing system”); United States v. Gray, 182 F.3d 762, 765
(10th Cir. 1999) (requiring prisoners to use the legal mail
system where a “prison maintains a legal mail system separate
from its regular mail system”); Porchia v. Norris, 251 F.3d 1196,
1198 (8th Cir. 2001) (noting that if a prison has “two internal
mail systems, one for regular mail and another for legal mail,”
the prisoner must use the legal mail system); 1998 Advisory
Comm. Note to Fed. R. App. P. 4(c) (stating that a legal mail
system is a “special internal mail system[] for handling legal
mail”). Hurlow’s statements regarding the system at F.C.I.
8                                                          No. 12-1374

Williamsburg for sending certified mail say nothing about the
existence of a separate system, let alone one for legal mail; they
are therefore not a “concession” regarding the existence of a
legal mail system for purposes of Rule 4(c).2
    Instead, the only evidence before us—Hurlow’s sworn
declarations—indicates that there was not a legal mail system
at F.C.I. Williamsburg at the time he sent his notice of appeal.
According to Hurlow, he asked the prison mailroom staff
whether he should place his envelope, which was addressed to
this Court, in the mailbox in his unit or directly in the hands of
the mailroom staff. The mailroom staff told him that “it made
no difference” whether he placed the envelope in his unit
mailbox or directly in the hands of the mailroom staff: either
method would be “as efficient” and the envelope would be
“considered delivered to the court at the moment” Hurlow
placed it in the unit mailbox or in the hands of the mailroom
staff. From this exchange between Hurlow and the prison
mailroom staff, which was clearly about the prison mailbox
rule, the only reasonable inference—assuming the competency
and honesty of the mailroom staff, which we will absent
evidence to the contrary—is that F.C.I. Williamsburg did not
have a legal mail system at the time he sent his notice of appeal
or he would have been informed of such system by the prison



2
   For the same reason, we reject the government’s reliance on 28 C.F.R.
§ 540.22, which provides that “[a]n inmate, at no cost to the government,
may send correspondence by registered, certified, or insured mail, and may
request a return receipt.” The fact that BOP regulations require F.C.I.
Williamsburg to have a procedure for sending certified mail likewise does
not mean there was a legal mail system within the meaning of Rule 4(c).
No. 12-1374                                                                  9

staff. We therefore reject the government’s arguments regard-
ing the existence of a legal mail system at F.C.I. Williamsburg.3
    We have said before that a prisoner who submits a declara-
tion under Rule 4(c)(1) must attest to “only two things”: the
date the notice was deposited into the prison mail system and
that first class postage was prepaid. Craig, 368 F.3d at 740.
Hurlow’s declaration meets this requirement.4 We therefore
conclude that Hurlow is entitled to the benefit of the prison
mailbox rule and his notice of appeal was timely.
    B. Hurlow’s § 2255 motion
    We now turn to the issue of whether Hurlow’s § 2255
challenge to his conviction is barred by the collateral review
waiver in his plea agreement. We review de novo the
enforceability of a plea agreement’s waiver of direct or
collateral review. Dowell v. United States, 694 F.3d 898, 901 (7th
Cir. 2012). It is well-settled that waivers of direct and collateral


3
   We note at this juncture that we remain puzzled as to why the govern-
ment failed to make any effort to investigate on its own whether F.C.I.
Williamsburg had a legal mail system at the time Hurlow sent his notice of
appeal. Had the government come forward with an affidavit or other
evidence attesting to the existence of a legal mail system at F.C.I.
Williamsburg, this would be a very different case. However, as we have
noted, Hurlow’s declarations are the only evidence in the record regarding
this issue.

4
    In a footnote in its initial brief addressing the timeliness of the appeal,
the government quibbled with Hurlow’s failure to specify that postage on
his pre-paid envelope was first-class postage, but it wisely abandoned that
argument given that the first-class nature of the postage is clear from other
statements in Hurlow’s declarations.
10                                                    No. 12-1374

review in plea agreements are generally enforceable. United
States v. Chapa, 602 F.3d 865, 868 (7th Cir. 2010); Jones v. United
States, 167 F.3d 1142, 1144–45 (7th Cir. 1999). Nevertheless,
because a plea agreement is a contract and generally governed
by ordinary contract law principles, waivers contained in the
agreements are unenforceable in certain circumstances akin to
those in which a contract would be unenforceable, such as
when the government has materially breached the agreement,
see United States v. Quintero, 618 F.3d 746, 750–52 (7th Cir.
2010), or the dispute falls outside the scope of the waiver,
Bridgeman v. United States, 229 F.3d 589, 591 (7th Cir. 2000).
    Though disputes over plea agreements are “usefully
viewed through the lens of contract law,” we have recognized
that the application of ordinary contract law principles to plea
agreements, “must be tempered by recognition of limits that
the Constitution places on the criminal process, limits that have
no direct counterparts in the sphere of private contracting.”
United States v. Bownes, 405 F.3d 634, 636 (7th Cir. 2005). For
example, “while a contracting party is bound by the mistakes
of his lawyer, however egregious (his only remedy being a suit
for malpractice), the Constitution entitles defendants entering
plea agreements to effective assistance of counsel.” Id. at 637.
We have therefore repeatedly recognized that appellate and
collateral review waivers cannot be invoked against claims that
counsel was ineffective in the negotiation of the plea agree-
ment. United States v. Jemison, 237 F.3d 911, 916 n.8 (7th Cir.
2001); United States v. Hodges, 259 F.3d 655, 659 n.3 (7th Cir.
2001); Bridgeman, 229 F.3d at 591.
No. 12-1374                                                          11

    Despite our precedent indicating that a collateral review
waiver does not prevent a habeas petitioner from being heard
on claims that his plea agreement was the product of ineffec-
tive assistance of counsel, the government argues, and the
district court concluded, that this avenue of relief from waiver
is not applicable to Hurlow because he has not alleged that his
counsel was ineffective in the negotiation of the waiver provision
of his plea agreement, as opposed to the agreement as a whole.
In support, the government relies upon Jones v. United States,
in which we stated that collateral review “waivers are enforce-
able as a general rule; the right to mount a collateral attack
pursuant to § 2255 survives only with respect to those discrete
claims which relate directly to the negotiation of the waiver.”
167 F.3d at 1145. But a more complete reading of Jones does not
support the government’s interpretation: we stated that “[t]he
right to appeal survives where the agreement is involuntary”
and reasoned that “[j]ustice dictates that a claim of ineffective
assistance of counsel in connection with the negotiation of a
cooperation agreement cannot be barred by the agreement
itself—the very product of the alleged ineffectiveness.” Id. at
1144–45 (emphasis added). And we enforced the waiver
provision in Jones not because the defendant failed to show
ineffectiveness with regards to the negotiation of the waiver
provision, but because the defendant made no showing
whatsoever with respect to his “naked assertions that he was
denied effective assistance of counsel and that the agreement
was involuntary.” Id. at 1145–46.5


5
    The government’s reliance on Mason v. United States, 211 F.3d 1065,
                                                          (continued...)
12                                                             No. 12-1374

    While we have repeated the less-than-artful phrase in Jones
regarding the “negotiation of the waiver,” e.g., United States v.
Sines, 303 F.3d 793, 798 (7th Cir. 2002), we have never held that
the waiver is unenforceable only when counsel is ineffective in
negotiating the specific waiver provision. Instead, our cases
since Jones have affirmed that an attorney’s ineffectiveness with
regard to the plea agreement as a whole, and not just the
specific waiver provision at issue, renders the waiver unen-
forceable. E.g., Bridgeman, 229 F.3d at 591 (“A plea agreement
that also waives the right to file a § 2255 motion is generally
enforceable unless the waiver was involuntary or counsel was
ineffective in negotiating the agreement.” (citation omitted));
Hodges, 259 F.3d at 659 n.3 (“[A] valid appellate waiver
contained in a plea agreement does not preclude a defendant’s
claim that the plea agreement itself was the product of ineffec-
tive assistance of counsel.” (citing Jones, 167 F.3d at 1144–45));
Jemison, 237 F.3d at 916 n.8 (“We have previously recognized
that a valid appellate waiver, though binding in other respects,
does not preclude judicial review of a criminal defendant’s
assertion that her plea agreement was itself the product of
ineffective assistance of counsel.” (citation omitted)). This is
because a “claim[] that the plea agreement was involuntary or


5
  (...continued)
1069–70 (7th Cir. 2000), is similarly misplaced. In Mason, we affirmed the
denial of the petitioner’s § 2255 motion based on the collateral review
waiver in his plea agreement. We noted, however, that Mason “never
claimed that his waiver was the result of ineffective assistance or that he did
not knowingly and voluntarily agree to the terms of the plea.” Id. at 1068.
Instead, his ineffective assistance of counsel claim related “only to his
attorney’s performance with respect to sentencing.” Id. at 1069.
No. 12-1374                                                       13

the result of ineffective assistance of counsel … concern[s] the
validity of the plea agreement,” and so it “would knock out the
waiver … along with the rest of the promises” if successful.
United States v. Behrman, 235 F.3d 1049, 1051 (7th Cir. 2000).
Thus, “a waiver stands or falls with the plea bargain of which
it is a part.” Quintero, 618 F.3d at 752 (citation omitted); see also
United States v. Sakellarion, 649 F.3d 634, 639 (7th Cir. 2011) (“Of
course, if a plea agreement is unenforceable, the waiver falls
with the agreement.”) (internal quotation marks and citation
omitted)); United States v. Cieslowski, 410 F.3d 353, 361–62 (7th
Cir. 2005) (“To the extent [the defendant’s] arguments, if
successful, would result in setting aside the plea agreement as
a whole, we entertain them despite the fact that the agreement
itself contains a waiver of appeal rights.”); United States v. Hare,
269 F.3d 859, 860 (7th Cir. 2001) (“A waiver of appeal is valid,
and must be enforced, unless the agreement in which it is
contained is annulled (for example, because involuntary).”
(citations omitted)); United States v. Wenger, 58 F.3d 280, 282
(7th Cir. 1995) (“Waivers … must stand or fall with the
agreements of which they are a part.”). We accordingly
reaffirm that a direct or collateral review waiver does not bar
a challenge regarding the validity of a plea agreement (and
necessarily the waiver it contains) on grounds of ineffective
assistance of counsel; Hurlow need not have alleged that his
counsel was ineffective in the negotiation of the waiver
provision of his plea agreement specifically.
    Our inquiry does not end here, however. Not every claim
of ineffective assistance of counsel can overcome a waiver in a
plea agreement. We have rejected broad, unsupported asser-
tions of ineffective assistance, see, e.g., Jones, 167 F.3d at
14                                                  No. 12-1374

1145–46, as well as “garden variety attacks … raise[d] in the
guise of a claim of ineffective assistance of counsel[,]” United
States v. Joiner, 183 F.3d 635, 645 (1999). We therefore must
determine whether Hurlow’s claims of ineffective assistance of
counsel are sufficient to overcome the waiver in his plea
agreement.
    Our analysis here is informed by cases in which a defendant
has pleaded guilty unconditionally, which, like a direct or
collateral review waiver, generally “forecloses any opportunity
to contest any alleged antecedent constitutional deprivations.”
Gomez v. Berge, 434 F.3d 940, 943 (7th Cir. 2006). In Tollet v.
Henderson, the Supreme Court explained the reasoning behind
this principle:
     [A] guilty plea represents a break in the chain of
     events which has preceded it in the criminal process.
     When a criminal defendant has solemnly admitted in
     open court that he is in fact guilty of the offense with
     which he is charged, he may not thereafter raise
     independent claims relating to the deprivation of
     constitutional rights that occurred prior to the entry of
     the guilty plea.
411 U.S. 258, 267 (1973). The Supreme Court recognized,
though, that a criminal defendant can bring claims “attack[ing]
the voluntary and intelligent character of the guilty plea[,]”
such as claims that the defendant “plead[ed] guilty on the
advice of counsel” that “was not ‘within the range of compe-
tence demanded of attorneys in criminal cases[.]’”Id. at 266–67
(quoting McMann v. Richardson, 397 U.S. 759, 771 (1970)). This
includes cases in which counsel has “fail[ed] to evaluate
No. 12-1374                                                      15

properly facts giving rise to a constitutional claim, or [failed to]
inform himself [properly] of facts that would have shown the
existence of a constitutional claim[.]” Id. at 266–67. The Su-
preme Court emphasized, however, that while the habeas
petitioner “must, of course, prove that some constitutional
infirmity occurred in the proceedings[,]” the “focus of federal
habeas inquiry is the nature of the advice and the voluntariness
of the plea, not the existence as such of an antecedent constitu-
tional infirmity.” Id. at 266. Nevertheless, while claims of prior
constitutional deprivations “are not themselves independent
grounds for federal collateral relief[,]” they “may play a part in
evaluating the advice rendered by counsel[.]” Id. at 267.
    The same is true for a petitioner such as Hurlow who seeks
to overcome the waiver provision in his plea agreement based
on ineffective assistance of counsel: he cannot just assert that a
constitutional violation preceded his decision to plead guilty or
that his trial counsel was ineffective for failing to raise the
constitutional claim. Rather, he must allege that he entered the
plea agreement based on advice of counsel that fell below
constitutional standards. In other words, he must allege that
the plea agreement was “the product of ineffective assistance
of counsel,” Jemison, 237 F.3d at 916 n.8, or “tainted by ineffec-
tive assistance of counsel,” United States v. Henderson, 72 F.3d
463, 465 (5th Cir. 1995). See also United States v. Teeter, 257 F.3d
14, 25 n.9 (1st Cir. 2001) (“This category [of situations in which
denying a right of appeal would work a miscarriage of justice]
is infinitely variable, but, by way of illustration, we would
include within it situations in which appellants claim … that
the plea proceedings were tainted by ineffective assistance of
counsel.” (citations omitted)); DeRoo v. United States, 223 F.3d
16                                                  No. 12-1374

919, 924 (8th Cir. 2000) (“[W]aiver of the right to seek section
2255 post-conviction relief does not waive defendant’s right to
argue, pursuant to that section, that the decision to enter into
the plea was not knowing and voluntary because it was the
result of ineffective assistance of counsel”). For example, in
United States v. Cieslowski, the defendant’s plea agreement
contained a waiver of direct and collateral review, but the
defendant claimed that his decision to enter into that plea
agreement was the product of his attorney’s ineffectiveness in
“fail[ing] to file two suppression motions[.]” 410 F.3d at 358,
360. Because this claim was the sort that, “if successful, would
result in setting aside the plea agreement as a whole,” we
considered (and ultimately rejected) the defendant’s ineffective
assistance of counsel argument on the merits. Id. at 361.
    Turning to Hurlow’s allegations in his § 2255 petition, we
similarly conclude that they are sufficient to overcome the
waiver in his plea agreement. First, he alleged that his trial
counsel was ineffective by failing to recognize that the detec-
tives who obtained the critical evidence against him did so in
violation of the Fourth Amendment: even though Hurlow
apprised him of facts that indicated that the search violated
Georgia v. Randolph, counsel refused to listen or investigate
further. See Tollet, 411 U.S. at 266–67 (“Counsel’s failure to
evaluate properly facts giving rise to a constitutional claim, or
his failure properly to inform himself of facts that would have
shown the existence of a constitutional claim, might in particu-
lar fact situations meet this standard of proof.”). Second,
Hurlow alleged that his decision to plead guilty resulted from
counsel’s ineffectiveness. According to Hurlow, counsel failed
to inform him that a challenge to the search was possible, and
No. 12-1374                                                     17

instead “persuaded” and “cajoled” him into pleading guilty by
telling him “that if [he] did not plead guilty, that [he] would
[receive] 30 years to life imprisonment.” Hurlow alleged that
had he known he could “contest the unconstitutional and
unreasonable search[,]” he “would not have entered into the
one-sided government authorized plea agreement” or “pled
guilt[.]” Thus, Hurlow is saying that he would not have agreed
to the terms of the plea agreement had his counsel informed
him of his potentially meritorious Fourth Amendment claim.
Cf. Cieslowski, 410 F.3d at 360 (“He does not say, however, that
he would have not pleaded guilty but for the erroneous
advice.”). This is sufficient to overcome the collateral review
waiver in his plea agreement.
    Seeking to avoid this result, the government argues that
Hurlow affirmed his satisfaction with counsel when he
“knowingly and voluntarily” pleaded guilty after a “thorough
Rule 11 colloquy.” But as we discuss above, a plea, even one
that complies with Rule 11, cannot be “knowing and volun-
tary” if it resulted from ineffective assistance of counsel. See
United States v. Jordan, 870 F.2d 1310, 1317 (7th Cir. 1989) (“A
guilty plea is intelligent and knowing when the defendant is
competent, aware of the charges, and advised by competent
counsel.” (citation omitted)); see also Brady v. United States, 397
U.S. 742, 748 (1970) (“Waivers of constitutional rights[,]” such
as guilty pleas, “not only must be voluntary but must be
knowing, intelligent acts done with sufficient awareness of the
relevant circumstances and likely consequences.”). It is not
surprising that Hurlow said he was satisfied with counsel;
when he told his counsel about the facts surrounding the
search, his lawyer ignored him. Thus, his statement to the
18                                                 No. 12-1374

district court was made against the backdrop of his ignorance
regarding the possibility of a successful motion to suppress.
    Moreover, aside from his dissatisfaction with counsel,
Hurlow’s allegations in his § 2255 petition are not inconsistent
with the factual basis for his plea or the statements he made
under oath during the Rule 11 colloquy. Hurlow does not
dispute that Funk gave her written consent to the search.
Rather, he claims Funk’s consent resulted from a coercive
police threat and that he objected to the search prior to Funk’s
consent. Thus, nothing we have said in any way undercuts the
fact that representations made to a court during “a plea
colloquy are presumed to be true.” United States v. Chavers, 515
F.3d 722, 724 (7th Cir. 2008).
    In reaching the conclusion that the collateral review waiver
in Hurlow’s plea agreement does not bar his claim that his
guilty plea resulted from ineffective assistance of counsel, we
offer no opinion regarding the veracity of Hurlow’s allegations
or the ultimate outcome of his collateral attack. Our inquiry
here is focused on whether Hurlow’s allegations entitle him to
an evidentiary hearing on his § 2255 motion. We conclude that
they do, and accordingly remand the case to the district court
for a hearing on Hurlow’s Sixth Amendment claim.
                     III. CONCLUSION
   For the foregoing reasons, we REVERSE the district court’s
denial of Hurlow’s petition and REMAND for further proceed-
ings consistent with this opinion.
