Milton v. Miller

FILED
United States Court of Appeals
PUBLISH Tenth Circuit

UNITED STATES COURT OF APPEALS February 9, 2016

Elisabeth A. Shumaker
FOR THE TENTH CIRCUIT Clerk of Court
_________________________________

ANTONIO DON MILTON,

Petitioner - Appellant,

v. No. 15-6069

DAVID MILLER,

Respondent - Appellee.
_________________________________

Appeal from the United States District Court
for the Western District of Oklahoma
(D.C. No. 5:10-CV-01367-F)
_________________________________

Submitted on the briefs:*

John T. Carlson, Office of the Federal Public Defender, Denver, Colorado, for Petitioner-
Appellant.

Jay Schniederjan, Office of the Attorney General for the State of Oklahoma, Oklahoma
City, Oklahoma; Joshua L. Lockett, Office of the Attorney General for the State of
Oklahoma, Oklahoma City, Oklahoma, for Respondent-Appellee.
_________________________________

Before MATHESON, MURPHY, and PHILLIPS, Circuit Judges.
_________________________________

PHILLIPS, Circuit Judge.
_________________________________

*
After examining the briefs and appellate record, this panel has determined
unanimously that oral argument would not materially assist in the determination of
this appeal. See Fed. R. App. P. 34(a)(2); 10th Cir. R. 34.1(G). The case is therefore
ordered submitted without oral argument.
 Antonio Don Milton, an Oklahoma state prisoner, requests a certificate of

appealability (COA) to appeal the district court’s denial of his 28 U.S.C. § 2254

petition for habeas relief. Exercising jurisdiction under 28 U.S.C. §§ 1291

and 2253(a), we deny Milton’s request for a COA.

I. BACKGROUND

We have previously detailed Milton’s history in Oklahoma state courts and the

federal district court. See Milton v. Miller, 744 F.3d 660, 663–68 (10th Cir. 2014).1

Milton’s case returns to us after we reversed the district court’s denial of his habeas

petition solely regarding Milton’s ineffective-assistance-of-appellate-counsel claim

and remanded for an evidentiary hearing on a narrow factual dispute, which, once

resolved, would assist the district court in better assessing the merits of Milton’s

remaining ineffective-assistance claim. See id. at 673. With evidence from the

hearing now available to us, we have the necessary facts to assess Milton’s claim.

Because the evidentiary hearing revealed new facts not known to courts that have

previously addressed Milton’s post-conviction claims, we recount Milton’s journey

through the criminal-justice system for the sake of clarity and coherence with our

earlier opinion.

A. State Court Proceedings

In 2007, Milton was prosecuted in two separate cases pending simultaneously

before a state district court. One included a charge for Milton’s trafficking in cocaine

1
In his initial habeas appeal, we granted Milton’s request for a COA only “to
appeal the dismissal of his claim of ineffective assistance based on counsel’s alleged
failure to inform him of the plea offer.” R. vol. 1 at 959; see id. at 953–59.
2
base (crack cocaine),2 while the other case concerned his involvement in a drive-by

shooting.3 Separate attorneys represented Milton in each case: Jacob Benedict, a

public defender, represented Milton in the drug-trafficking case until Michael Arnett

took over after the preliminary hearing; Joe Reynolds, a private attorney, represented

Milton in the drive-by-shooting case. Because Milton had two earlier felony drug-

trafficking convictions, the crack-cocaine-trafficking charge mandated life without

parole upon conviction. See Okla. Stat. tit. 63, § 2-415(D)(3) (2004) (“If the person

has previously been convicted of two or more violations of this section or any

provision of the Uniform Controlled Dangerous Substances Act which constitutes a

felony, or a combination of such violations arising out of separate and distinct

transactions, [his sentence shall be a term of imprisonment of] life without parole.”).

The State extended Milton at least one plea offer that covered at least one of

Milton’s two cases. The parties have disputed the terms of the offered plea deal (or

deals) throughout Milton’s pretrial and post-conviction proceedings. But Milton

ultimately rejected the offered plea deal(s) and went to trial in the drug-trafficking

case. He was convicted of the crack-cocaine-trafficking charge and sentenced to the

2
In this case, a jury convicted Milton of: trafficking in cocaine base after two
or more previous felony convictions (mandatory life without parole); possession of a
firearm after two or more previous felony convictions (consecutive life sentence with
a possibility of parole); possession of marijuana after two or more previous felony
convictions (consecutive ten years); and possession of drug paraphernalia
(consecutive one year). We refer to this case as the “drug-trafficking case.”
3
Milton was formally charged with using a vehicle to facilitate the intentional
discharge of a firearm, but for brevity we refer to this case as the “drive-by-shooting
case.”
3
mandatory term of life without parole. After this, the State let the drive-by-shooting

case lapse, leaving the court to dismiss it for lack of prosecution.

On direct appeal, Katrina Conrad-Legler represented Milton. The Oklahoma

Court of Criminal Appeals (OCCA) affirmed all of Milton’s convictions and

sentences, including the drug-trafficking conviction with its mandatory life-without-

parole sentence. Later, Milton filed a pro se application for post-conviction relief and

requested an evidentiary hearing in Oklahoma state district court. Relevant here,

Milton argued “that his appellate counsel rendered ineffective assistance by failing to

assert on direct appeal that Milton’s trial counsel was ineffective for failing to inform

Milton of a plea-bargain offer made by the prosecution prior to the preliminary

hearing.” Milton, 744 F.3d at 664.

Milton’s ineffective-assistance claim had some basis in the record. At a

pretrial hearing in the drug-trafficking case, Judge Twyla Mason Gray mentioned

that, sometime before his preliminary hearing, Milton had rejected an offered plea

deal providing for a 23-year sentence in the drug-trafficking case.4 Upon hearing

Judge Gray say this, Milton told his counsel at the time of trial, Arnett, who then told

Judge Gray, that Milton had never heard about a 23-year offer. In response to the

confusion, the prosecutor at the pretrial hearing, Ashley Altshuler, referenced the

notes of Benjamin McGoldrick, the prosecutor who handled the case until leaving the

4
Specifically, Judge Gray said, “I cannot remember exactly what we put on
the record earlier, but the defendant had the opportunity to plead guilty and receive
23 years [in the drug-trafficking case] prior to preliminary hearing and he turned that
down.” R. vol. 2 at 215.
4
office sometime after December 2007. McGoldrick’s notes reflected that on the day

of a preliminary-hearing conference,5 he offered Milton a plea deal of 25 years’

incarceration in the drug-trafficking case, to run concurrently with 20 years’

incarceration in the drive-by-shooting case (25/20 Deal).6 Now better informed,

Judge Gray declared irrelevant any plea deals McGoldrick had offered Milton before

the preliminary hearing because those deals had expired. Given this factual

background, Milton argued that his direct-appeal counsel had ineffectively assisted

him by not raising his trial counsel’s ineffectiveness in not telling Milton about the

23-year offer Judge Gray had mentioned.

The State opposed Milton’s application for post-conviction relief, relying

principally on an affidavit Jacob Benedict (Milton’s public defender) submitted,

when the State supposedly had offered Milton the 23-year deal. In his affidavit,

Benedict recounted two plea deals the State had offered to Milton before the

preliminary hearing. The plea deals contained essentially the same terms, differing

only on the date they were communicated: Milton was offered 20-year concurrent

5
The preliminary-hearing conference, distinct from the preliminary hearing,
took place on August 2, 2007. The preliminary hearing took place on October 30,
2007.
6
Only if the prosecutor reduced Milton’s pending drug-trafficking charge
could Milton avoid the mandatory life-without-parole sentence upon conviction. See
R. vol. 2 at 126 (“Q: . . . [W]ould it be fair to conclude that on the 2nd of August you
offered Joe Reynolds a package deal on both cases: 25, possession with intent, and 20
on the drive-by? A: It would have been to reduce the trafficking to possession with
intent, give him 25 on that, 25 on all the other counts contingent on him taking 20
years to do on the drive-by shooting. . . . Q: You just have to drop the trafficking to
possession with intent? A: Yes, ma’am. Q: Okay. And that automatically takes life
without parole off the table? A: Yes, ma’am.”).
5
sentences in the drug-trafficking case and the drive-by-shooting case (20/20 Deal).

The affidavit noted that McGoldrick originally offered the 20/20 Deal sometime

before the preliminary-hearing date, and that McGoldrick also offered the same deal

just before the hearing began. According to Benedict’s affidavit, Milton rejected the

offers, and the parties proceeded with the preliminary hearing.

Based partly on this information, the state district court denied Milton’s

application for post-conviction relief on his ineffective-assistance-of-appellate-

counsel claim, concluding that “[t]here is nothing submitted in the record which

indicates that appellate counsel’s performance rendered the result unreliable or the

proceeding fundamentally unfair.” R. vol. 1 at 214. On appeal, the OCCA affirmed,

citing Strickland v. Washington, 466 U.S. 668, 687 (1984), and holding as follows:

[I]n order to prevail on his claim of ineffective assistance of
appellate counsel, [Milton] must establish counsel made errors so
serious the performance was deficient, and that the deficient
performance deprived him of an appeal whose results are reliable
and fair. The fact appellate counsel fails to recognize or raise a
claim, regardless of merit, is not sufficient alone to establish
ineffective assistance of counsel, or to preclude enforcement of a
procedural default. We [find Milton] has not established appellate
counsel’s performance was deficient, or that the result of his
appeal was not reliable and fair.

R. vol. 1 at 236–37 (citation omitted) (emphasis added). Thus, as Milton’s

application for post-conviction relief proceeded through Oklahoma courts, the courts

6
considered conflicting evidence about offers for the 20/20 Deal, the 25/20 Deal, and

a supposed 23-year deal.7

The timing, communication, and existence of each of these deals matter.

Obviously, had McGoldrick offered Milton the 20/20 Deal minutes before the

preliminary hearing, Milton could not have suffered prejudice from any earlier failure

by his counsel to communicate a less favorable 23-year offer. But had McGoldrick

offered Milton the 25/20 Deal before the preliminary hearing, Milton could have

suffered prejudice if his counsel failed to communicate a more favorable 23-year deal

before the preliminary hearing. But the state courts denied Milton relief without ever

determining whether McGoldrick had offered a 23-year deal and, if so, whether

Milton’s counsel had told Milton about it.

B. Federal Habeas Proceedings

Milton next filed a pro se habeas petition under 28 U.S.C. § 2254 in the United

States District Court for the Western District of Oklahoma. Milton alleged various

claims for relief, including the same ineffective-assistance-of-appellate-counsel claim

he had argued in the state courts:

Appellate counsel, Katrina Conrad-Legler, rendered ineffective
assistance by failing to raise in [Milton]’s direct appeal the
following sub-proposition[] of trial counsel’s deficienc[i]es: . . .
Trial attorney, Joe Reynolds, rendered ineffective assistance by
failing to inform [Milton] of a (pre-preliminary hearing) plea-
bargain offer of 23 years on all counts until the day set for trial,
and well after the plea offer had been withdrawn.

7
At this stage of the proceedings, it was unclear whether the supposed 23-year
plea offer related to the drug-trafficking case, the drive-by-shooting case, or both.
7
R. vol. 1 at 29 (capitalization omitted). The magistrate judge assigned to Milton’s

case issued a report recommending that the district court deny Milton’s habeas

petition in its entirety.

In concluding that Milton’s ineffective-assistance claim lacked merit, the

magistrate judge referenced Benedict’s affidavit, the same one that the state courts

had relied upon to deny Milton’s claim. Milton argued that the 20/20 Deal referenced

in the affidavit was a different plea deal than the one Milton had complained of in his

habeas petition (i.e., the 23-year deal). The magistrate judge interpreted Milton’s

argument as conceding the truth of the affidavit. From this, the magistrate judge

concluded that Milton could not have suffered any prejudice from not hearing about

the 23-year offer since he had already rejected the more favorable 20/20 Deal.

Accordingly, the magistrate judge recommended that the district court deny Milton’s

petition because he had failed to show any prejudice.

Milton objected to the magistrate judge’s report and recommendation. He

conceded that he had been offered a 20-year plea deal in the drive-by-shooting case

but denied receiving any offers in the drug-trafficking case—whether the purported

offer was the 25/20 Deal or the 23-year deal. He claimed that he first heard of both

the 25/20 Deal and the 23-year deal when Altshuler and Judge Gray discussed the

pre-preliminary-hearing plea offers on the eve of trial. Therefore, Milton argued that

either Benedict was lying in his affidavit about having conveyed to him the offered

20/20 Deal or that Benedict had confused the drug-trafficking case with the drive-by-

shooting case. Milton noted that “[t]he issue” was that no one had “informed [him] of

8
any pre-preliminary hearing plea offer in [the drug-trafficking case], and as a direct

result, rather than serving a twenty-five (25) year sentence with all counts running

concurrently,” he was serving a life sentence without the possibility of parole. R. vol.

1 at 894. From this, he contended that he had been “prejudiced by trial counsel’s

failure to timely inform him of the State’s pre-preliminary hearing plea offer of

twenty-five (25) years in [the drug-trafficking case].” Id. The confusion over the

offers for the 20/20 Deal, the 25/20 Deal, and the 23-year deal persisted. Was Milton

now arguing that his trial counsel had failed to communicate the 25/20 Deal and the

23-year deal he mentioned in his habeas petition? If so, the record does not show that

he expressed surprise at the pretrial hearing after Altshuler told Judge Gray about the

pre-preliminary-hearing plea offer of the 25/20 Deal.

Leaving Milton’s objections unaddressed, the district court simply adopted the

magistrate judge’s report and recommendation. The district court declined to grant a

COA, but we later granted Milton’s pro se request for a COA on his ineffective-

assistance-of-appellate-counsel claim and appointed Milton counsel to assist with his

appeal.

In Milton, we concluded that the OCCA’s ineffective-assistance analysis was

contrary to clearly established federal law and that Milton had overcome the bar that

28 U.S.C. § 2254(d)(1) imposed. Milton, 744 F.3d at 669–70. Specifically, we

concluded that the OCCA “rendered meaningless” its prejudice analysis under

Strickland “[b]y ignoring the merits of the underlying predicate claim in assessing

appellate counsel’s performance.” Id. at 670. In this regard, we held that the OCCA

9
had “deviated from the controlling federal standard.” Id. (quoting McGee v. Higgins,

568 F.3d 832, 839 (10th Cir. 2009)). With § 2254(d)(1)’s bar no longer in play, we

then reviewed de novo Milton’s Strickland claim.

Applying the two-pronged Strickland framework, we first concluded that

Milton’s appellate counsel, upon reviewing Milton’s trial transcripts, should have

seen and raised as an issue that Milton’s trial attorney had “failed to promptly and

meaningfully convey to Milton the existence of a plea offer made by the prosecution

at some point” before the preliminary hearing. Id. at 671. The trial counsel’s failure,

we concluded, would have been “inconsistent with prevailing professional norms and

[would have given] rise to a viable claim of ineffective assistance of trial counsel.”

Id. We therefore held that “[b]y failing to discover and raise the issue [of trial

counsel’s ineffectiveness] on direct appeal, Milton’s appellate counsel clearly

performed deficiently.” Id.

In addition, the Milton court considered under Strickland’s second prong

“whether Milton was prejudiced by his appellate counsel’s deficient performance.”

Id. We concluded that the state courts and the federal district court had erred by

finding, based solely on Benedict’s affidavit and in the face of conflicting evidence,

that Milton had suffered no prejudice from his appellate counsel’s ineffective

assistance. We noted that prejudice depended on whether Milton’s counsel had failed

to convey to Milton any plea offer in the drug-trafficking case: “Assuming, for

purposes of argument, that Milton is truthfully alleging that he was not informed of

any pre-preliminary-hearing plea offer, and that he would have accepted such offer

10
had he been timely informed of it, that is clearly sufficient to establish

prejudice . . . .” Id. at 672.

We concluded that Milton was entitled to a federal evidentiary hearing to

resolve this factual dispute because the appellate record did not give us sufficient

information to do so.8 The evidentiary hearing would bring forth crucial facts: either

(1) that Milton’s trial counsel had indeed failed to communicate a favorable plea

deal, which likely would satisfy Strickland’s prejudice prong, or (2) that Milton’s

trial counsel had communicated the most favorable plea deal, meaning Milton’s

ineffective assistance claim would fail to satisfy Strickland’s prejudice prong. As

explained below, the evidentiary hearing produced facts that did not fit squarely into

either category.

8
We further concluded that, in this case, 28 U.S.C. § 2254(e)(2) would not
preclude the district court from holding an evidentiary hearing. By asking for an
evidentiary hearing on the ineffective-assistance claim in the state courts, Milton
hadn’t “failed to develop the factual basis” of his claim. 28 U.S.C. § 2254(e)(2); see
Williams v. Taylor, 529 U.S. 420, 432 (2000) (“Under the opening clause of
§ 2254(e)(2), a failure to develop the factual basis of a claim is not established unless
there is lack of diligence, or some greater fault, attributable to the prisoner or the
prisoner’s counsel.”); Stouffer v. Trammell, 738 F.3d 1205, 1219 (10th Cir. 2013)
(“[The prisoner’s] counsel asked the trial court for a hearing . . . . As the State
concedes, he raised the issue in his state application for post-conviction relief . . . .
This is sufficient to satisfy § 2254(e)’s diligence requirement.”).
11
C. The Evidentiary Hearing

On remand, the district court held an evidentiary hearing to resolve the factual

dispute regarding the nature of Milton’s plea offers. We recount the testimony

relevant to this appeal.9

1. McGoldrick’s Testimony

The testimony of Benjamin McGoldrick, the prosecutor assigned to both of

Milton’s cases until McGoldrick left the office sometime after December 2007,

produced three important facts.

First, McGoldrick testified that he never communicated a 23-year plea deal to

either Benedict or Reynolds, notwithstanding his case-file notes referencing a

possible plea offer for a 23-year sentence in the drug-trafficking case and a

concurrent 23-year sentence in the drive-by-shooting case (23/23 Deal).10

Importantly, these notes about the possible 23/23 Deal are dated December 18,

2007—well after the October 30, 2007 preliminary hearing. McGoldrick testified that

he wrote the notes about the possible 23/23 Deal as a potential recommendation if

Milton’s attorneys agreed to resolve the case without trial at a pretrial conference

scheduled for the following day, December 19, 2007. But critically, McGoldrick

9
The attorney who represented Milton in the drive-by-shooting case, Joe
Reynolds, died before the evidentiary hearing. He therefore could not testify about
his recollection of the events in Milton’s case.
10
The note in McGoldrick’s file for the drug-trafficking case read: “Rec: 23 to
do; amend Count 2 to [possession with intent].” R. vol. 2 at 140–41. His note in his
file for the drive-by-shooting case: “rec: 23 to do c/c with [the drug-trafficking
case].” Id.
12
testified that he in fact never communicated an offer for the 23/23 Deal to either of

Milton’s attorneys. McGoldrick also testified that he was uncertain how Judge Gray

knew anything about his notes for the 23/23 Deal at the pretrial conference where she

mentioned it.

Second, McGoldrick testified that on August 2, 2007, with Milton present, he

communicated the 25/20 Deal at least to Reynolds, Milton’s counsel in the drive-by-

shooting case. McGoldrick’s file notes for each case substantiate the existence and

communication of the 25/20 Deal. That offer remained pending before the

preliminary hearing on October 30, 2007. And McGoldrick also testified that he

made Milton a better offer in the courtroom immediately before the preliminary

hearing began: the 20/20 Deal. McGoldrick did not write a case-file note about

having offered the 20/20 Deal.

Third, McGoldrick testified that on August 17, 2007, he told Reynolds,

without Milton present, that if Milton succeeded in getting the drive-by-shooting case

dismissed, McGoldrick would “probably” pursue the life-without-parole sentence in

the drug-trafficking case.11 R. vol. 2 at 137. This effectively meant McGoldrick

“probably” wouldn’t make any plea offer that reduced Milton’s pending drug-

11
Specifically, McGoldrick said:

I told Reynolds that the offer on both cases would go away if this
case, being the drive-by case, got dismissed. I would probably
proceed with the recommendation of life without parole if the
case got dismissed. Mr. Reynolds said he wanted to talk to the
defendant and his family about it.

R. vol. 2 at 137.
13
trafficking charge—the only way Milton could escape Oklahoma’s mandatory life-

without-parole sentence applying to that charge. In other words, the 25/20 Deal—the

sole offer pending on August 17, 2007—was a package deal, and McGoldrick would

continue to insist on guilty pleas in both cases.12 McGoldrick testified that he never

discussed this approach to prosecuting the cases with Benedict, Milton’s counsel in

the drug-trafficking case.

2. Altshuler’s Testimony

At the evidentiary hearing, the court also heard from Ashley Altshuler, the

prosecutor who took over the drug-trafficking and drive-by-shooting cases after

McGoldrick left the district attorney’s office. Most importantly, Altshuler explained

how Judge Gray had heard of a 23-year deal: “I believe we had a conversation and I

just had the files in front of me and I believe she [Judge Gray]—there may have been

a discussion of what the offer was before the prelim.” R. vol. 2 at 215–16. Simply

put, Judge Gray knew about a 23-year deal because Altshuler had conversed with

Judge Gray while undoubtedly referencing what turned out to be McGoldrick’s

written musings about possibly offering the 23/23 Deal—as stated, a possible offer in

fact never made.

12
McGoldrick insisted on Milton’s serving a substantial sentence. In
Oklahoma, the drive-by-shooting charge was an “85 percent crime,” one conditioning
parole eligibility on service of 85% of the sentence imposed. R. vol. 2 at 67. Thus,
had Milton accepted offers for the 25/20 or 20/20 Deal, he likely would have served
about 17 years concurrently on both offenses. Accordingly, Milton’s prison time
might well have been the same whether Milton pleaded to the 25/20 Deal or the
20/20 Deal. He would have been eligible for parole in the drug-trafficking case long
before he was eligible for parole in the drive-by-shooting case.
14
 Understandably, after reading McGoldrick’s notes, Altshuler thought that

McGoldrick had offered Milton the 23/23 Deal. But Altshuler already knew that

McGoldrick had dated his notes about the 23/23 Deal December 18, 2007, nearly two

months after the preliminary hearing. Accordingly, Altshuler told Judge Gray that the

pre-preliminary hearing offer had been “25 on possession with intent with all other

counts to run concurrent and then also to run concurrent with the 20 in [the drive-by-

shooting case]. It was before prelim.” R. vol. 2 at 216.

Amid the multiple plea offers and dates, Judge Gray made an honest mistake.

Contrary to Judge Gray’s misunderstanding, McGoldrick had not even contemplated

offering the 23/23 Deal Judge Gray had heard about in her conversation with

Altshuler until after the preliminary hearing, not before it. The 25/20 Deal was the

sole offer pending before the preliminary hearing, just as Altshuler had told Judge

Gray based on McGoldrick’s notes. A relative newcomer to the case, Altshuler had

no way to know about McGoldrick’s offering the 20/20 Deal to Milton in the

courtroom immediately before the preliminary hearing began—as mentioned,

McGoldrick did not write a note in the file about the offer or Milton’s refusal of it.

Altshuler also could not have known from McGoldrick’s notes whether McGoldrick

ever offered Milton the 23/23 Deal, whether on December 18, 2007, or after.

3. Benedict’s Testimony

Jacob Benedict, the public defender who represented Milton in the drug-

trafficking case, also testified at the evidentiary hearing. Benedict’s case notes and

testimony revealed two important facts.

15
 First, Benedict’s case notes indicated that McGoldrick had offered the 25/20

Deal sometime before the preliminary-hearing date.13 Benedict also testified that he

recalled, even without any notes, that McGoldrick offered the 20/20 Deal in the

courtroom before the preliminary hearing began. Benedict also admitted that he may

have erred in the portion of his affidavit where he stated that the pending offer before

the preliminary-hearing date was the 20/20 Deal. Instead, after viewing McGoldrick’s

case files, Benedict conceded that it probably had been the 25/20 Deal. In addition,

Benedict still recalled McGoldrick’s having offered the 20/20 Deal in the courtroom

before the preliminary hearing began, consistent with his earlier statement in a

different portion of his affidavit.

Second, Benedict corroborated McGoldrick’s earlier testimony: McGoldrick

had communicated to Reynolds, but not to Benedict, that McGoldrick would continue

to pursue the drug-trafficking case as already charged—resulting in a mandatory life-

without-parole sentence in the drug-trafficking case—if the court ultimately

dismissed the drive-by-shooting case.14 Despite McGoldrick’s failure to communicate

this prosecution position to both of Milton’s attorneys, Benedict recalled that

13
Benedict had written a note in his file for the drug-trafficking case saying:
“reduce Count 2 to 25 and possession with intent.” R. vol. 2 at 245. This note was
located directly below a notation memorializing a 20-year offer in the drive-by-
shooting case and above a note indicating the “offer is open until prelim.” R. vol. 1 at
1037. Benedict testified at the evidentiary hearing that, based on these notes, the
25/20 Deal had been conveyed to him.
14
Benedict also corroborated McGoldrick’s testimony that McGoldrick never
offered the 23/23 Deal.
16
Reynolds discussed every other detail relevant to Milton’s plea offers at the

preliminary hearing, when Milton and both of his attorneys were present:

Q: [W]as it ever discussed that a plea might be in Mr.
Milton’s best interest?

A: Well, absolutely. And that would have been the October
30th meeting where—which essentially Joe Reynolds
was on point talking with Mr. Milton about the fact that
what the offer was, which would have been the 20-year
offer on the drive-by case, but that he needed to take
care of both of them because they weren’t parsing them
out or splitting them up for us.

* * *

[On October 30, 2007, at the preliminary hearing,] I
remember it vividly that Mr. Reynolds was essentially
telling Mr. Milton that he needed to take the offer from
the state. And what I remember vividly was Mr. Milton
with his head down shaking his head referencing the
drive-by case, that he just—that seemed to be what
drove him in his decision-making.

[Court]: So are you telling the Court that Mr. Reynolds was
fairly unequivocal in his recommendation that Mr.
Milton take the then pending deal in the drive-by case?

[A]: Yes.

[Court]: And that was for [] what sentence?

17
 [A]: That was for a 20-year sentence, which he would have
had to serve 85 percent of that sentence. And I recall it
as a 20 on possession with intent, but notes within the
documents here indicate that it was a 25-year sentence
on possession with intent, all running together,
concurrent, at the same time.

R. vol. 2 at 273–76.15

4. Milton’s Testimony

Milton also testified at the evidentiary hearing. Relevant to this appeal, Milton

admitted receiving a 20-year plea offer for the drive-by-shooting case on the day of

the preliminary hearing, but he testified that he never received any plea offer in the

drug-trafficking case. Milton also testified that no one ever told him that any plea

offer in one of his two pending cases was contingent on his accepting an offer in the

other case. Finally, Milton testified that Reynolds never told him that the State would

probably continue to pursue its pending drug-trafficking charge (carrying a

mandatory sentence of life without parole) if Milton somehow obtained a dismissal in

the drive-by-shooting case.

15
Benedict recounted his vivid recollection of the meeting between him,
Milton, and Reynolds later in his testimony, perhaps more succinctly:

Mr. Reynolds drove it. I think Mr. Milton had a lot more respect
for Mr. Reynolds, just because he’s a private attorney, and
seemed to listen to him. Mr. Reynolds seemed to control the
conversation. And he just discussed the case, discussed the fact
that both cases were contingent upon a plea in each case, and that
that was probably in his best interest, even though—despite him,
Mr. Milton, maintaining his innocence in the [drive-by-shooting]
case.

R. vol. 2 at 280.
18
D. Petition Denied

The district court directed Milton’s habeas counsel and the State to submit

proposed findings of fact and conclusions of law after the evidentiary hearing.

Ultimately, the district court denied Milton’s petition for habeas relief. In doing so,

the district court first reviewed the question we posed on remand: “whether petitioner

received constitutionally ineffective assistance of appellate counsel as a result of

counsel’s failure to pursue, during appellate proceedings, a possible claim of

ineffective assistance of trial counsel for failure to communicate a 23-year plea offer”

before the October 30, 2007 preliminary hearing. R. vol. 1 at 1155. For clarity, we

will refer to this particular habeas claim as Milton’s “Original Claim.”

The district court denied Milton’s Original Claim because, as the evidentiary

hearing revealed, McGoldrick considered offering Milton the 23/23 Deal, but

McGoldrick never did. In view of this, the district court concluded that Milton’s

ineffective-assistance-of-appellate-counsel claim failed for lack of prejudice.

Although that ordinarily would have ended the matter, the district court further

addressed two brand-new habeas claims Milton fashioned from testimony at the

evidentiary hearing. First, the district court turned to what we will term Milton’s

“New Claim”: Reynolds was ineffective for “blatantly fail[ing] to communicate the

complete terms of the State’s offer.” Id. at 1167. More specifically, Milton argued

that Reynolds had failed to communicate McGoldrick’s “warning” that McGoldrick

would continue to pursue the pending drug-trafficking charge (again, carrying a

mandatory sentence of life without parole) if Milton somehow obtained a dismissal in

19
the drive-by-shooting case. Second, the district court defined what we will term

Milton’s “Other New Claim”: After the preliminary hearing but before trial, Michael

Arnett, Milton’s new public defender in the drug-trafficking case, “failed to attempt

any negotiation on Mr. Milton’s behalf,” “[denying Milton] the opportunity to

resolve his exposure to punishment for terms of years significantly less than” life

without parole. Id.

At the outset, the district court held as a matter of law that Milton had failed to

exhaust his new claims in the state court. The district court noted that this procedural

basis alone was sufficient to dismiss Milton’s new claims. But the district court also

addressed the merits of both new claims, ultimately concluding that each lacked

merit. The district court denied Milton’s petition for habeas relief and later declined

to grant a COA.

Milton now petitions this court for a COA. We address all of Milton’s claims

below, both old and new.

II. DISCUSSION

Before Milton can appeal to this court, we must grant him a COA. 28 U.S.C.

§ 2253(c)(1)(A). We may grant a COA only if the petitioner makes a “substantial

showing of the denial of a constitutional right.” Id. § 2253(c)(2). This requires a

“showing that reasonable jurists could debate whether (or, for that matter, agree that)

the petition should have been resolved in a different manner or that the issues

presented were adequate to deserve encouragement to proceed further.” Slack v.

McDaniel, 529 U.S. 473, 484 (2000) (quotation marks omitted). To obtain a COA

20
after a district court has rejected a petitioner’s constitutional claims on the merits, the

“petitioner must demonstrate that reasonable jurists would find the district court’s

assessment of the [petitioner’s] constitutional claims debatable or wrong” to obtain a

COA. Id.

In requesting a COA, Milton has not reasserted his true Original Claim as

such. The evidence defeated his claim that his trial counsel had failed to convey a 23-

year offer (because no such offer was ever made). Instead, Milton now tries to stretch

the canopy of his Original Claim to cover one of his new claims. Even though Milton

has abandoned his true Original Claim, we still find it prudent to address the Original

Claim to show that Milton is wrong that his new claims are mere amplifications of

his Original Claim.

A. The Original Claim

We do not grant Milton a COA with respect to his Original Claim because

Milton does not ask for one. Instead, Milton has wisely abandoned this claim in his

current request.

The evidentiary hearing served its purpose. The testimony at the hearing made

sense of the conflicting evidence noted in Milton. The hearing established, and

Milton does not contest, that McGoldrick never communicated the 23/23 Deal to

either Reynolds or Benedict because the 23/23 Deal existed only in Benedict’s mind

and notes. Obviously, trial counsel could not be ineffective for failing to convey to

Milton an offer that the prosecutor never made. In turn, Milton suffered no Strickland

prejudice for his appellate counsel’s failure to raise what turned out to be a losing

21
issue. Our de novo review of Milton’s original ineffective-assistance-of-appellate-

counsel claim, which began with Milton, is now complete.

B. The New Claims

Despite fulfilling the goal of our remand, we must address what the district

court termed Milton’s “new claims” to the extent Milton pursues them in his current

request for a COA.16

1. Amplification or Alteration?

Milton argues that his request for a COA does not abandon his Original Claim

but includes evidence that merely “clarif[ies] or amplif[ies] the claim he made in his

original petition for relief.”17 Pet’r’s Request at 30. Milton essentially attempts to

recast his Original Claim in broad language that would encompass both his Original

Claim and New Claim. Instead of referencing the narrow language of his habeas

petition, for example, which explicitly references Reynolds’s failure to communicate

a 23-year deal, Milton argues in his request that “[h]is theory remains unchanged:

16
We note that the district court concluded that Milton had actually crafted
two new claims from evidence at the hearing. We do not address the Other New
Claim, however, because Milton has abandoned this claim in his current request for a
COA. In his request, Milton did not even reference the factual predicate for the Other
New Claim—that Arnett was ineffective for failing to negotiate a plea deal after the
preliminary hearing. We note, though, that the Other New Claim is distinct from his
Original Claim, which primarily concerned the pre-preliminary-hearing conduct of
Milton’s counsel. Although both claims involve counsel’s ineffectiveness, that hardly
makes them the same claim.
17
Milton argues that we must construe his pro se habeas petition liberally and
that his original petition reflected what Milton knew at the time. We agree that
Milton’s pro se petition should be construed liberally, but “we will not rewrite a
petition to include claims that were never presented.” Parker v. Champion, 148 F.3d
1219, 1222 (10th Cir. 1998).
22
because of information withheld by his lawyer, Milton forwent a favorable plea offer.

That’s what he alleged in his original petition and that’s what he alleges here.” Id. at

31. We reject Milton’s attempt to cast his habeas petition in a more favorable light.

Although Milton cites authority one would normally cite to amend a habeas

petition, Milton simultaneously argues that his claim remains unchanged (i.e.,

unamended). Id. at 29–30 (citing Fed. R. Civ. P. 15(c)(2); Mayle v. Felix, 545 U.S.

644, 650 (2005)). He argues that he has always claimed that “one of his trial lawyers

failed to inform him of a plea offer made by the prosecutor before the October 30

preliminary hearing.” Id. at 30. We disagree that that is what he has always claimed,

noting that the New Claim has a dramatically different factual predicate: that

Reynolds failed to communicate McGoldrick’s “warning” to continue prosecuting the

pending drug-trafficking charge if Milton somehow obtained a dismissal in the drive-

by-shooting case. Although this claim and the Original Claim both allege ineffective

assistance of counsel, they are separate claims. Milton cannot allege an ineffective-

assistance claim and then usher in anything fitting under that broad category as the

same claim. Counsel can perform ineffectively in myriad ways. See Hammon v.

Ward, 466 F.3d 919, 926 n.8 (10th Cir. 2006) (considering one ineffective-

assistance-of-appellate-counsel claim but refusing to consider another such claim

because the petitioner “did not raise [the latter] claim in his § 2254 habeas petition,

and we therefore will not consider it on appeal”). Further, we note that Milton’s COA

request has abandoned his original argument that his appellate counsel was

ineffective. Instead, he now argues that Reynolds, his trial counsel, was ineffective.

23
We fail to see how a claim based on trial counsel’s ineffectiveness merely amplifies a

claim based on appellate counsel’s ineffectiveness. To the extent Milton is asking us

to consider his habeas petition as amended, we note that Milton has never sought to

amend his habeas petition, even after the evidentiary hearing, and we cannot allow

him to do so now.18 Milton’s New Claim is indeed new.

2. Presentation and Exhaustion

Generally, Milton must have presented his New Claim in his written habeas

petition for federal courts to consider it. See Rules Governing Section 2254 Cases,

Rule 2(c), 28 U.S.C. foll. § 2254; Adams v. Armontrout, 897 F.2d 332, 334 (8th Cir.

1990) (“We hold that in order to substantially comply with the Section 2254 Rule

2(c), a petitioner must state specific, particularized facts which entitle him or her to

habeas corpus relief for each ground specified. These facts must consist of sufficient

detail to enable the court to determine, from the face of the petition alone, whether

the petition merits further habeas corpus review.”). Milton must also have exhausted

his New Claim in state court for federal courts to consider it on the merits. Cullen v.

Pinholster, 563 U.S. 170, 181 (2011) (“Sections 2254(b) and (c) provide that a

federal court may not grant [a habeas] application[] unless, with certain exceptions,

the applicant has exhausted state remedies.”). Milton’s New Claim meets neither

18
In his request, Milton goes so far as to argue the following: “Now that
Milton has [new pieces of evidence], he has inserted them and their meaning into the
record and into his petition, as he is authorized by Rule 15(c), to clarify or amplify
what has always been his position . . . .” Pet’r’s Request at 33 (emphasis added).
24
requirement. Milton’s New Claim appears nowhere in his habeas petition and he

never presented the New Claim to state courts for review.

Ordinarily in this situation, the habeas section of the Antiterrorism and

Effective Death Penalty Act of 1996 (AEDPA), 28 U.S.C. § 2254, dictates that we

decline Milton’s request for a COA on his New Claim for failure to exhaust but leave

open the possibility that Milton might be able to return to the Oklahoma state courts

to try to present his New Claim. AEDPA’s structure and policy favors states having

the first opportunity to resolve claims their prisoners make. See O’Sullivan v.

Boerckel, 526 U.S. 838, 845 (1999) (“[T]he exhaustion doctrine is designed to give

the state courts a full and fair opportunity to resolve federal constitutional claims

before those claims are presented to the federal courts . . . .”). But Milton’s case is

procedurally unusual for two reasons, both of which justify treating his New Claim

differently.

First, despite the New Claim not appearing in Milton’s habeas petition, the

district court still chose to reject the New Claim on its merits. The district court did

not reject Milton’s New Claim based solely on exhaustion or the claim’s failure to

appear on the face of the petition. Second, Milton bases his New Claim on evidence

newly revealed at the evidentiary hearing, although outside our narrow remand. With

this procedural background, we choose to address the merits of the unexhausted New

Claim in determining whether to grant Milton’s request for a COA. In doing so, we

stress that new claims arising from this unusual procedural setting are not excused

from Rule 2(c)’s petition requirements or the exhaustion requirement.

25
 Ordinarily, to present his new claims on the merits, Milton would have to

amend his habeas petition to add his new claims, 28 U.S.C. § 2242, or file a second

or successive habeas application in accordance with § 2244, see Carter v. Bigelow,

787 F.3d 1269, 1277–81 (10th Cir. 2015) (concluding that a habeas petitioner adding

new claims rather than adding evidence in support of the “precise” claims in his

habeas petition must follow the procedures in § 2244). But sending his New Claim

back to the district court after the district court already addressed the New Claim on

the merits would only unnecessarily belabor these proceedings.

Similarly, we address Milton’s New Claim despite its being unexhausted

because § 2254(b)(2) allows the district court to do so if the New Claim lacks merit.

“An application for a writ of habeas corpus may be denied on the merits,

notwithstanding the failure of the applicant to exhaust the remedies available in the

courts of the State.” 28 U.S.C. § 2254(b)(2); see Moore v. Schoeman, 288 F.3d 1231,

1235 (10th Cir. 2002) (“[Under § 2254(b)(2),] a district court faced with a habeas

petition containing unexhausted claims may either (1) dismiss the entire petition

without prejudice in order to permit exhaustion of state remedies, or (2) deny the

entire petition on the merits.”). In the interest of judicial economy, our court has

often considered habeas claims on the merits despite a petitioner’s failure to exhaust.

See Allen v. Mullin, 368 F.3d 1220, 1235 (10th Cir. 2004) (reviewing de novo an

unexhausted claim and citing § 2254(b)(2)); Romero v. Furlong, 215 F.3d 1107, 1111

(10th Cir. 2000) (“Before addressing Appellant’s ineffective assistance arguments,

we note that this case presents a number of complex issues concerning the

26
applicability of Colorado’s procedural bar to these claims. We need not and do not

address these issues, however, because the case may be more easily and succinctly

affirmed on the merits.”).

We also note that we may address Milton’s New Claim because, “as the

Supreme Court has pointed out, the doctrine[] of exhaustion . . . raise[s] only federal-

state comity concerns and [is] not a jurisdiction[al] limitation of the power of the

court.” Cain v. Redman, 947 F.2d 817, 820 (6th Cir. 1991) (pre-AEDPA) (citing

Granberry v. Greer, 481 U.S. 129, 131–36 (1987)); Strickland v. Thaler, 701 F.3d

171, 174 (5th Cir. 2012) (post-AEDPA) (“While a district court should dismiss an

entire federal habeas application if the petitioner’s state remedies have not been

exhausted as to all claims raised in the federal petition, because exhaustion is based

on comity rather than jurisdiction, there is no absolute bar to federal consideration of

unexhausted habeas applications.” (quotation marks and citation omitted)).

3. Substantive Analysis

We note once more that because the district court denied Milton’s New Claim

on the merits, we should only grant a COA for the New Claim if “reasonable jurists

would find the district court’s assessment of the [petitioner’s] constitutional claims

debatable or wrong.” Slack, 529 U.S. at 484.

To succeed on the merits of his New Claim under Strickland, Milton must

show that: (1) appellate counsel “unreasonably failed to discover [a] nonfrivolous

issue[] and to file a merits brief raising [it]”; and (2) prejudice. Smith v. Robbins, 528

U.S. 259, 285 (2000); see Strickland, 466 U.S. at 694. In the context of a claim of

27
appellate-counsel ineffectiveness, a defendant can prove prejudice by showing “a

reasonable probability that, but for his counsel’s unreasonable failure to” raise the

nonfrivolous issue, “he would have prevailed on his appeal.” Robbins, 528 U.S. at

285. Because we do not believe reasonable jurists would find the district court’s

assessment of Milton’s New Claim debatable or wrong, we deny Milton’s request for

a COA.

Supporting his New Claim, Milton argues that the district court misunderstood

the value of Milton’s knowing the prosecutor’s planned approach to plea bargaining

in the drug-trafficking and drive-by-shooting cases. Specifically, Milton argues that,

on the day of the preliminary hearing when the State offered the 20/20 Deal, “he was

unaware of a vital fact: if the drive-by were indeed dismissed there would be no plea

bargaining forthcoming on the drug case. But this Milton didn’t know, precisely

because of his lawyer’s failure to communicate the full terms of the offer he was then

pondering.” Pet’r’s Request at 39 (emphases in original). The district court found that

this claim lacked merit on three grounds, but we address only one ground because it

resolves Milton’s New Claim.

Initially, we take issue with Milton’s argument because of its

mischaracterization of the “threatening warning” McGoldrick communicated to

Reynolds. Id. at 35. McGoldrick simply noted that he would “probably” refuse to

reduce the drug-trafficking charge (leaving intact its mandatory life-without-parole

sentence) if the drive-by-shooting case were dismissed. R. vol. 2 at 137. But Milton

characterizes this “warning” in more fatalistic, certain terms: “if the drive-by were

28
indeed dismissed there would be no plea bargaining forthcoming on the drug case.”

Pet’r’s Request at 39 (second emphasis added). McGoldrick’s position was not so

certain, given McGoldrick’s still mulling a possible deal (the 23/23 Deal) long after

the preliminary hearing.

Moreover, the district court noted that even if Reynolds had communicated

McGoldrick’s warning, “the evidence presented at the hearing thoroughly

undermines any suggestion that petitioner would have gone for” any of the offered

plea deals. R. vol. 1 at 1169. The district court further explained its reasoning:

Without the warning, petitioner knew that he could take a 20-
year, 85% deal on the drug case or stand trial and subject himself
to the virtual certainty of a sentence of life without parole. With
the warning, petitioner would have known, while he pondered a
20-year, 85% deal in the drug case, that if the drive-by case were
to be dismissed, he would still face a virtually certain sentence of
life without parole in the drug case.

Id. (emphases in original). We agree with the district court’s assessment.19

Milton argues that the district court should have added a third alternative:

Without the warning, Milton believed he could “reject the offers and defeat the drive-

by at the preliminary hearing, thereby reducing the charges he faced from two to

one . . . .” Pet’r’s Request at 38. Under this scenario, Milton argues that he “would

[have] be[en] free of the drive-by case, and he could then negotiate a discrete and

19
Milton correctly states that the district court appears to have mistaken the
drug-trafficking case for the drive-by-shooting case by referring to the drug-
trafficking charge as an 85% crime. But this mistake does not defeat the district
court’s sound logic in rejecting Milton’s New Claim.
29
singular plea bargain on the drug case.” Id. Milton couched this argument in the

appropriate legal standard:

In the absence of complete information, Milton took his chances.
He rejected the package plea hoping to drive a wedge between
two cases linked by fiat of the prosecutor, believing he could
defeat one on the evidence and negotiate a settlement of the
other. He lost his gamble. The drive-by survived the preliminary
hearing. The question, though, is this: would he have taken that
chance with full information before the hearing? The answer is
probably not. To be faithful to the formal legal standard, it is
more accurate to say there is a reasonable probability Milton
would have eschewed the gamble and instead accepted the 20/20
plea bargain, if only he had full information.

Id. at 39 (emphasis in original). But what Milton fails to argue is why he would

reasonably believe that the State would reduce his drug-trafficking charge to one not

carrying a mandatory life-without-parole sentence because Milton somehow obtained

dismissal in the drive-by-shooting case. That defies common sense. In addition,

Milton fails to explain why he would have changed his course had he heard of the

“warning” about continuing to prosecute the pending drug-trafficking charge (with its

mandatory sentence of life without parole) when he had already rejected the 25/20

Deal or the 20/20 Deal.20

20
The district court made no explicit finding of fact regarding which deal
McGoldrick ultimately offered Milton at the preliminary hearing. Rather, the court
noted the conflicting testimony we outlined above and concluded:

It does not appear that the question of whether the offer in the
drug case was a 20-year offer or a 25-year offer is of any
moment, because the only deal that would have ever been made
would have been a package deal including a 20-year sentence in
the drive-by case, which would have been an 85% sentence.
Thus, the difference being considered for parole in the drug case,
30
 Reynolds told Milton that the existing plea deal was a package offer—he

would receive no stand-alone offer in either case. See R. vol. 2 at 280 (“Mr. Reynolds

seemed to control the conversation. And he just discussed the case, discussed the fact

that both cases were contingent upon a plea in each case, and that that was probably

in his best interest, even though—despite him, Mr. Milton, maintaining his innocence

in the [drive-by-shooting] case.”). To any reasonable jurist, Milton’s poor “gamble”

was the cause of his current predicament, not the lack of any additional “warning”

from Reynolds. Milton knew, based on his conversation with Reynolds on the day of

the preliminary hearing, that any existing offer would expire if Milton proceeded

with the imminent preliminary hearing, let alone if Milton continued to seek

dismissal of the drive-by-shooting case. Even so, Milton rejected the offer and opted

for a preliminary hearing on a pending charge that provided for and ultimately

resulted in his life-without-parole sentence.

Even after Reynolds told Milton that any existing deal would expire if he

chose to proceed with a preliminary hearing, Milton apparently hoped against all

odds that McGoldrick would inexplicably reduce Milton’s pending drug-trafficking

charge if Milton succeeded in getting his drive-by-shooting case dismissed. But

after serving one third of a 20-year sentence or one third of a 25-
year sentence is of no consequence because petitioner would, in
any event, have been required to serve 85% of a 20-year sentence
in the drive-by case.

R. vol. 1 at 1161 n.2. Milton abandons his position that he never heard about the
25/20 Deal or the 20/20 Deal in his request for a COA.
31
Milton knew that McGoldrick was not obliged to make any offer and was not

inclined to make an offer on just one of Milton’s cases.

Because we do not believe reasonable jurists could debate that Milton’s New

Claim lacks merit based on Milton’s argument above, we deny Milton’s related

request for a COA.

III. CONCLUSION

New evidence discovered at the federal evidentiary hearing has assisted our de

novo review of Milton’s ineffective-assistance claims, and we conclude that all of

them lack merit. Accordingly, we deny Milton’s request for a COA on all bases

presented.

32