                      United States Court of Appeals
                           FOR THE EIGHTH CIRCUIT
                                    ___________

                                    No. 11-1547
                                    ___________

Charles Samuel Watson, Jr.,            *
                                       *
            Petitioner - Appellant,    *
                                       * Appeal from the United States
      v.                               * District Court for the
                                       * Southern District of Iowa.
United States of America,              *
                                       *
            Respondent - Appellee.     *
                                  ___________

                              Submitted: January 13, 2012
                                 Filed: June 26, 2012
                                  ___________

Before BYE, SMITH, and COLLOTON, Circuit Judges.
                            ___________

BYE, Circuit Judge.

       Pursuant to 28 U.S.C. § 2255, Charles Watson, Jr., filed a motion to vacate the
165-month sentence he received after he pleaded guilty to a drug conspiracy charge.
The district court1 summarily denied the motion because Watson waived the right to
bring a § 2255 motion in his plea agreement. We granted a certificate of appealability
on the issue of whether the waiver was enforceable to the extent Watson claimed
ineffective assistance of counsel in matters directly related to his plea agreement. We
now affirm.

      1
       The Honorable John A. Jarvey, United States District Judge for the Southern
District of Iowa.
                                          I

       On October 5, 2008, Watson delivered heroin to Joseph Vanhoe in Iowa City,
Iowa. Within a few hours, Vanhoe was found dead in his apartment. Vanhoe had a
fresh needle mark in his arm. Police found two hypodermic needles with liquid inside
them near Vanhoe's body, along with several baggie corners containing heroin
residue. An autopsy concluded Vanhoe died from ethanol and heroin poisoning.

       A federal grand jury indicted Watson with: (1) conspiring to distribute cocaine
base and heroin resulting in death in violation of 21 U.S.C. §§ 841(a)(1), (b)(1)(A),
(b)(1)(C), and 846; (2) distribution of heroin resulting in death in violation of 21
U.S.C. § 841(a)(1) and (b)(1)(C); and (3) distribution of heroin in violation of 21
U.S.C. § 841(a)(1) and (b)(1)(C). Watson pleaded guilty to the conspiracy count
pursuant to a written plea agreement. The conspiracy count carried a mandatory
minimum sentence of 240 months due to the allegation that death resulted from the
distribution of the controlled substances involved in the conspiracy. See 21 U.S.C.
§ 841(b)(1)(C) (mandating "a term of imprisonment of not less than twenty years" for
cases involving schedule I or II controlled substances "if death or serious bodily
injury results from the use of such substance").

      In the plea agreement, Watson waived the right to file a direct appeal of his
sentence. He also waived the right to collaterally attack his sentence. The relevant
provision in the plea agreement stated:

      Waiver of Right to Collateral Attack. The defendant also understands
      that he has a right to attack his conviction, and/or the sentence imposed,
      collaterally on the grounds that it was imposed in violation of the
      Constitution or laws of the United States; that the defendant received
      ineffective assistance from his attorney; that the Court was without
      proper jurisdiction; or that the conviction and/or sentence were
      otherwise subject to collateral attack. The defendant understands that

                                         -2-
      such an attack is usually brought through a motion pursuant to 28 U.S.C.
      § 2255. The defendant and the defendant's attorney have reviewed
      Section 2255, and the defendant understands applicable rights under the
      statute. The defendant's attorney has fully discussed and explained the
      defendant's right to attack the conviction and/or sentence collaterally
      with the defendant. Understanding those rights, and having thoroughly
      discussed those rights with his attorney, the defendant knowingly and
      voluntarily waives the right to collaterally attack his conviction and/or
      sentence. The defendant specifically acknowledges that the decision to
      waive the right to challenge any later claim of the ineffectiveness of his
      counsel was made by him alone notwithstanding any advice he may or
      may not have received from his attorney regarding that right.
      Regardless of any advice the defendant's attorney may have given him,
      in exchange for the concessions made by the United States in this
      Agreement, the defendant hereby knowingly and voluntarily waives the
      right to collaterally attack the conviction and/or sentence. The rights
      waived by the defendant include the right to challenge the amount of
      any fine or restitution in any collateral attack including, but not limited
      to, a motion brought under Section 2255.

Plea Agreement at ¶ 14.

      During Watson's plea hearing, the district court discussed the collateral attack
waiver with Watson. The following colloquy took place:

      THE COURT: People who get done appealing, going as far as they can
      go, ordinarily have a right for a period of one year to bring a limited
      attack on their conviction. Sometimes it is called post conviction relief,
      sometimes it is referred to by the criminal code Section 2255 that it is
      filed under usually in Federal Court. I see in Paragraph 14 of the Plea
      Agreement that you have given up that as well. In the Plea Agreement
      it says that you understand that you have that right, that you and your
      lawyer have discussed that right, and that understanding the right to
      bring that limited attack, you knowingly and voluntarily waive or give
      up the right to collaterally attack your conviction or sentence.
      Oftentimes this right is used to bring a claim that your lawyer rendered

                                         -3-
      ineffective assistance of counsel, that your lawyer just wasn't up to the
      task or left something out or did something wrong along the way. Here
      in the Plea Agreement it says, "The defendant specifically acknowledges
      that the decision to waive the right to challenge any later claim of
      ineffective assistance of his counsel was made by him alone,
      notwithstanding any advice he may or may not have received from his
      attorney regarding that right." So you don't get to bring a claim later
      that Mr. Ingram was ineffective in recommending this plea
      agreement. Do you understand that?

      THE DEFENDANT: Yes, sir.

Plea Tr. at 15-16 (emphasis added).

      The district court later sentenced Watson to 165 months of imprisonment,
departing below the 240-month mandatory minimum after granting the government's
motion for a substantial assistance departure under 18 U.S.C. § 3553(e). The other
two counts against Watson were dismissed pursuant to the plea agreement.

       Within a year after being sentenced, Watson filed a motion to vacate his
sentence under 28 U.S.C. § 2255. The motion alleged four grounds for setting aside
the conviction and sentence: (1) the sentence was illegal because it was based upon
a finding Watson was responsible for fifty grams or more of cocaine base even though
the presentence report (PSR) only attributed 1.6 grams of cocaine base directly to
Watson; (2) the sentence was illegal due to the enhancement based on Joseph
Vanhoe's death; (3) the receipt of improper advice from his attorney with regard to
entering into the cooperation agreement with the government; and (4) ineffective
assistance of counsel, including ineffective advice Watson received regarding the plea
agreement itself.

      The district court denied the section 2255 motion without an evidentiary
hearing, enforcing the collateral attack waiver in Watson's plea agreement. The

                                         -4-
district court also later denied Watson's request for a certificate of appealability.
Watson renewed his request for a certificate of appealability in our court. We granted
Watson's request in part, limiting it "to the question whether the district court
correctly enforced Watson's waiver of his right to attack his conviction and sentence
in a proceeding under 28 U.S.C. § 2255 based on ineffective assistance of counsel."
This appeal followed.

                                           II

       We review issues related to plea agreements de novo, including the
interpretation of a waiver of appellate rights or a waiver of the right to collaterally
attack a sentence and conviction. See United States v. Lovelace, 565 F.3d 1080, 1084
(8th Cir. 2009).

       Citing DeRoo v. United States, 223 F.3d 919 (8th Cir. 2000), Watson argues
the district court erred in enforcing the collateral attack waiver in his plea agreement
because he alleged in his section 2255 motion that the guilty plea itself was tainted
by ineffective assistance of counsel in violation of his Sixth Amendment rights. In
DeRoo, we stated the "[d]ismissal of a section 2255 motion on the basis of a waiver
in the plea agreement is inappropriate when the defendant's claims of ineffective
assistance relate to the negotiation of, and entry into, the plea agreement and waiver."
223 F.3d at 924. We determined a "decision to enter into a plea agreement cannot be
knowing and voluntary when the plea agreement itself is the result of advice outside
'the range of competence demanded of attorneys in criminal cases.'" Id. at 923-24
(quoting Hill v. Lockhart, 474 U.S. 52, 56 (1985)). Thus, "justice 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 924 (quoting Jones v. United States, 167 F.3d
1142, 1145 (7th Cir. 1999)).



                                          -5-
      Our court subsequently noted the tension between a broad reading of DeRoo
and the Supreme Court's long recognition of a defendant's ability to waive rights
guaranteed by the Sixth Amendment, including the right to effective assistance of
counsel. See Chesney v. United States, 367 F.3d 1055, 1058 (8th Cir. 2004) (citing
Johnson v. Zerbst, 304 U.S. 458, 468-69 (1938)). In Chesney, we explained:

      If a criminal defendant is able to negotiate substantial concessions from
      the prosecution, but only on the condition that the defendant waive a
      potential future claim of ineffective assistance of counsel, does "justice"
      really dictate that this court refuse to enforce such an agreement in all
      circumstances? If the government cannot obtain the benefit of avoiding
      collateral litigation under section 2255, then the government may not be
      willing to offer certain concessions, and a defendant may be unable to
      secure the bargain most favorable to his interests. To require that
      conclusion would seem, in Justice Frankfurter's famous words, "to
      imprison a man in his privileges and call it the Constitution." Adams v.
      United States ex rel. McCann, 317 U.S. 269, 280, 63 S.Ct. 236, 87 L.Ed.
      268 (1942).

Id. at 1058-59.

      Chesney suggested that perhaps DeRoo should be refined to stand for the
following proposition:

      [A] general waiver of the right to bring post-conviction or
      post-sentencing claims under section 2255 would not be sufficient to
      waive such a claim of ineffective assistance of counsel, but an explicit
      waiver of the Sixth Amendment right to counsel – which explained the
      concept of ineffective assistance of counsel and the basic ramifications
      of waiving a claim that ineffectiveness influenced the signing of the
      waiver – would be considered knowing and voluntary. Cf. Faretta v.
      California, 422 U.S. 806, 835-36, 95 S.Ct. 2525, 45 L.Ed.2d 562 (1975).
      Under the law of this circuit, so long as such a waiver of Sixth



                                         -6-
       Amendment rights did not result in a "miscarriage of justice," Andis,
       333 F.3d at 891-92, the waiver would be enforceable.

Id. at 1059.

        Chesney ultimately did not adopt such a refinement of DeRoo because
"Chesney's waiver did not specifically mention the Sixth Amendment or the right to
effective assistance of counsel, and the colloquy with the court at the time of
sentencing was no more specific than the general written waiver." Id. The
government nonetheless urges us to adopt Chesney's dicta as a holding in this case
because the collateral attack provision in Watson's plea agreement explicitly referred
to the right to bring a claim for ineffective assistance of counsel, and the district court
specifically discussed the waiver with Watson during the plea colloquy.

        We are not inclined to decide whether to adopt Chesney's refinement of DeRoo
in this particular case, however, because the parties failed to address an issue we find
difficult to ignore in determining whether Watson knowingly and voluntarily waived
his right to bring an ineffective assistance claim with respect to matters directly
related to the plea agreement. Ethics opinions from various states have addressed
whether a defendant's attorney labors under a conflict of interest when advising a
client to waive an ineffective assistance of counsel claim, with conflicting results.2

      2
        Compare Prof'l Ethics Comm. for the State Bar of Tex. Op. No. 571 (2006)
(concluding a defense lawyer who has "no cause for any reasonable concern as to his
effectiveness in representing the defendant" would not have a conflict of interest in
advising a client to waive an ineffective assistance claim), and Ariz. State Bar Comm.
on the Rules of Prof'l Conduct Op. 95-08 (1995) (concluding a defense lawyer may
advise a client to waive an ineffective assistance claim because "[t]here is a
significant difference between a defendant's claim that a court should revisit his
sentence because of ineffective assistance of counsel and a defendant's claim against
his lawyer [for malpractice]"), with Ala. State Bar Formal Ethics Op. RO 2011-02
(2011) (concluding "a conflict of interest exists where a lawyer must counsel his
client on whether to waive any right to pursue an ineffective assistance of counsel

                                           -7-
Watson does not claim his counsel labored under a conflict of interest when advising
him to enter the plea agreement, and the parties did not brief this issue. We therefore
believe it prudent to forego the issue of whether DeRoo should be refined by
Chesney's suggestions until this related issue on a potential conflict of interest is fully
aired by the adversarial process.

       Instead, we accept the government's invitation to determine whether the district
court should be affirmed in any event because Watson's ineffective assistance claim
fails on the merits. See United States v. Castellanos, 608 F.3d 1010, 1015 (8th Cir.
2010) (noting waiver is a prudential rather than a jurisdictional concept and does not
bar appellate review). In order to satisfy the prejudice prong of the Strickland3 test
in the guilty plea context, a defendant must establish a reasonable probability that he
would have exercised his right to a trial but for counsel's ineffectiveness. Hill, 474
U.S. at 59. On appeal, Watson never directly contends he would not have pleaded
guilty and would have insisted on going to trial but for his counsel's alleged
deficiencies. Instead, he claims he can show prejudice because his section 2255
motion challenges "the aspects of his conviction which led to his 20 year mandatory
minimum sentence – the allegations that he was involved in a conspiracy to distribute
more than 50 grams of cocaine, and that his involvement in the alleged distribution
of heroin led to the death of Joseph Vanhoe."


claim against himself"), Nev. Standing Comm. on Ethics and Prof'l Responsibility,
Formal Op. No. 48 (2011) (same), Va. State Bar Legal Ethics Op. No. 1857 (2011)
(same), and Advisory Comm. of the Sup. Ct. of Mo. Formal Op. 126 (2009) (same);
see also Bd. of Comm'rs on Grievances & Discipline of the Sup. Ct. of Ohio Op.
2001-6 (2001) (concluding a lawyer's advice to enter a plea agreement that waives an
ineffective assistance claim is an unethical attempt to limit liability for personal
malpractice); Vt. Bar Ass'n Comm. on Prof'l Responsibility, Advisory Ethics Op. 95-
04 (1995) (same).
      3
        Strickland v. Washington, 466 U.S. 668, 687-94 (1984) (setting forth the two-
part standard for evaluating claims of ineffective assistance of counsel).

                                           -8-
      Watson's contention that he faced a mandatory minimum sentence of 240
months because the conspiracy involved fifty grams or more of cocaine base is
incorrect. As we stated above, Watson faced a mandatory minimum sentence of 240
months because the conspiracy involved a death resulting from the distribution of
heroin. Thus, Watson's admission that the conspiracy involved fifty grams or more
of cocaine had no bearing on the mandatory minimum sentence he faced. As a result,
he cannot establish any prejudice due to any advice he may have received from his
counsel in that regard.

       With respect to Watson's second contention—that his counsel failed to
investigate Watson's involvement in Vanhoe's death—the record establishes "Watson
admitted he delivered heroin to Vanhoe on the day of Vanhoe's death[.]" PSR at ¶ 24.
The autopsy report indicated Vanhoe died from heroin poisoning. In addition, one
of Watson's codefendants, Reginald Penro, was shown the heroin seized from
Vanhoe's residence and "stated it appeared to be the same substance he and Watson
delivered to Vanhoe on the day of Vanhoe's death." Id. at ¶ 21. Watson fails to
address the strength of this evidence or otherwise explain how his trial counsel was
ineffective in failing to further investigate whether Watson's conduct resulted in
Vanhoe's death. We therefore conclude that Watson cannot establish he was
prejudiced by his counsel's alleged ineffective assistance, and thus the district court
did not abuse its discretion in denying the relief Watson requested without holding
an evidentiary hearing.

                                          III

      We affirm the district court.
                      ______________________________




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