United States v. Nelson

UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF COLUMBIA

______________________________
)
UNITED STATES OF AMERICA )
)
v. ) Criminal Action No. 11-59 (RWR)
)
GREGORY SCOTT NELSON, )
)
Defendant. )
______________________________)

MEMORANDUM OPINION AND ORDER

Gregory Nelson pled guilty to traveling from Virginia to

Washington, D.C. to engage in illicit sexual conduct, in

violation of 18 U.S.C. § 2423(b), and was sentenced to 25 months

of imprisonment. Nelson’s later 28 U.S.C. § 2255 motion to

vacate his sentence was granted on the ground that Nelson’s

guilty plea was involuntary since the government violated its

duty to disclose material exculpatory evidence to Nelson. The

government now moves for reconsideration of the Memorandum

Opinion and Order (“Opinion”) granting Nelson’s motion. Because

the government has failed to demonstrate a clear legal error,

the government’s motion will be denied.

BACKGROUND

The facts are more extensively described in the earlier

Opinion. United States v. Nelson, No. 11-59 (RWR), 2013 WL

5778318 (D.D.C. Oct. 25, 2013).
 -2-

Briefly, Nelson pled guilty to traveling from Virginia to

Washington, D.C. to engage in illicit sexual conduct and was

sentenced to a 25-month term of imprisonment. A year after he

was sentenced, Nelson filed a motion under 28 U.S.C. § 2255,

alleging that his guilty plea was “induced through the

government’s violation of its constitutional obligation to

produce exculpatory evidence under Brady v. Maryland” because

the government failed to disclose an e-mail (“1:44 p.m. e-mail”)

and that Nelson “did not receive the effective assistance of

counsel.” Petitioner Gregory Nelson’s Mot. to Vacate, Set Aside

or Correct Sentence Under 28 U.S.C. § 2255 (“Nelson’s § 2255

Mot.”) at 1. Nelson’s Brady v. Maryland claims were fully

briefed before the Opinion was issued, although briefing on his

ineffective assistance of counsel claims had not concluded.

Nelson’s motion to vacate his conviction and permitting him

to withdraw his guilty plea was granted in the Opinion issued on

October 25, 2013. Nelson, 2013 WL 5778318. The Opinion

concluded that “[b]ecause the prosecution suppressed exculpatory

evidence before Nelson pled guilty, Nelson’s due process rights

were violated to his prejudice and his guilty plea was not

voluntary and knowing.” Nelson, 2013 WL 5778318 at *9. The

Opinion suspended briefing on the ineffective assistance of

counsel claim. Id.
 -3-

The government now moves for reconsideration of the

Opinion, arguing that (1) “the Order reflects an overly narrow

reading of United States v. Ruiz, 536 U.S. 622 (2002), and draws

a distinction between impeachment material and other exculpatory

evidence which the text of that opinion does not support”; (2)

“the Order inappropriately relieves defendant of the

ramifications of his actual possession of the e-mail he claims

the government withheld from him”; and (3) “the Order bypasses

the well-recognized principles of Brady v. United States, 397

U.S. 742 (1970), and its progeny, which articulate the standard

for assessing the voluntariness of a plea.” Govt.’s Mot. to

Reconsider This Court’s Order Granting Def.’s 28 U.S.C. § 2255

Mot. (“Govt.’s Mot.”) at 2-3. The government asserts that “the

court misunderstood the government’s arguments and misconstrued

the holding in United States v. Ruiz, with the result that the

Court’s ruling reflects a clear error of law.” Govt.’s Reply to

Nelson’s Opp’n to the Govt.’s Mot. to Reconsider This Court’s

Order Allowing Def. to Withdraw His Guilty Plea (“Reply”) at 3

n.2. Nelson opposes. Nelson’s Opp’n to the Govt.’s Mot. to

Reconsider This Court’s Order Granting Def.’s 28 U.S.C. § 2255

Mot. (“Opp’n”).

DISCUSSION

The government did not identify a rule under which it is

moving for reconsideration. However, the government “does not
 -4-

take issue with the [defendant’s] suggestion that the proper

avenue for a motion to reconsider should be found in the civil

rules of procedure, rather than in this Court’s criminal

jurisprudence.” Reply at 2. Accordingly, the government’s

motion will be assessed under Federal Rule of Civil Procedure

59(e). Id. at 3 (acknowledging that the “motion to reconsider

is properly filed under Rule 59(e) or Rule 60(b)” (citing

Ackerland v. United States, 633 F.3d 698, 701 (8th Cir. 2011));

see also Owen-Williams v. BB & T Inv. Servs., Inc., 797 F. Supp.

2d 118, 121-22 (D.D.C. 2011) (“As a general matter, courts treat

a motion for reconsideration as originating under Rule 59(e) if

it is filed within 28 days of the entry of the order at issue

and as originating under Rule 60(b) if filed thereafter.”

(footnote omitted)).

Under Federal Rule of Civil Procedure 59(e), a party may

request that a court reconsider its earlier judgment. “While

the court has considerable discretion in ruling on a Rule 59(e)

motion, the reconsideration and amendment of a previous order is

an unusual measure.” City of Moundridge v. Exxon Mobil Corp.,

244 F.R.D. 10, 12 (D.D.C. 2007) (internal quotation marks

omitted). “A motion to alter the judgment need not be granted

unless there is an intervening change of controlling law, new

evidence becomes available, or there is a need to correct a
 -5-

clear error or prevent manifest injustice.” Id. (citing Messina

v. Krakower, 439 F.3d 755, 758 (D.C. Cir. 2006)).

“[A] losing party may not use a Rule 59 motion to raise new

issues that could have been raised previously.” Kattan by

Thomas v. District of Columbia, 995 F.2d 274, 276 (D.C. Cir.

1993); see also Fed. Deposit Ins. Corp. v. Meyer, 781 F.2d 1260,

1268 (7th Cir. 1986) (“[Motions to alter or amend a judgment]

cannot be used to raise arguments which could, and should, have

been made before the judgment issued.”). Rather, “‘where

litigants have once battled for the court’s decision, they

should neither be required, nor without good reason permitted,

to battle for it again.’” Hoffman v. District of Columbia, 681

F. Supp. 2d 86, 90 (D.D.C. 2010) (quoting Singh v. George Wash.

Univ., 383 F. Supp. 2d 99, 101–02 (D.D.C. 2005)); Singh, 383 F.

Supp. 2d at 101-02 (denying motion for reconsideration because

“the Court considered the cases that the [defendant] now cites”

and the “attempt to re-litigate this issue will not be

countenanced”). A Rule 59 motion is also “not simply an

opportunity to reargue facts and theories upon which a court has

already ruled.” New York v. United States, 880 F. Supp. 37, 38

(D.D.C. 1995); see also Miss. Ass’n of Coops. v. Farmers Home

Admin., 139 F.R.D. 542, 546 (D.D.C. 1991) (“[A] motion for

reconsideration must address new evidence or errors of law or
 -6-

fact and cannot merely reargue previous factual and legal

assertions.”).

I. RUIZ

The government argues that permitting Nelson to withdraw

his guilty plea on the basis of a Brady v. Maryland violation is

“both inconsistent with the Supreme Court’s analysis in Ruiz . .

. and unsupported by the law” since the Court in Ruiz “declined

to impose on the government a pre-plea obligation under Brady v.

Maryland” and the “balance of circuit precedent post-Ruiz weighs

against an extension of Brady v. Maryland doctrine to the plea

context.” Govt.’s Mot. at 6 (internal quotation marks omitted).

The government’s arguments -- that Ruiz should be read

broadly to say that the government has few, if any, pre-plea

Brady v. Maryland obligations, and that, post-Ruiz, other courts

have refused to extend the Brady v. Maryland obligation to pre-

plea situations -- were both raised and rejected previously.

See Govt.’s Response to “Brady” Claim in Def.’s Mot. to Vacate,

Set Aside or Correct Sentence Under 28 U.S.C. § 2255 (“Govt.’s

Brady Opp’n”) at 15-16 (arguing that Ruiz makes it “unclear that

[a] valid Brady[ v. Maryland] claim justifies withdrawing [a]

guilty plea”); id. (“Since Ruiz, a number of Courts have

rejected defendant’s argument [that he can withdraw his plea

based on Brady[ v. Maryland] violations].”); Govt.’s

Supplemental Mem. on Def.’s “Brady” Allegation, Following Oral
 -7-

Argument (“Govt.’s Supp. Brady Mem.”) at 15 (arguing that the

Supreme Court in Ruiz “concluded that the Constitution does not

require the government to disclose Brady[ v. Maryland]

impeachment evidence before entering a plea agreement with a

criminal defendant”); Nelson, 2013 WL 5778318, at *3-5 (finding

that Ruiz did not decide whether the government has a pre-plea

obligation to disclose Brady v. Maryland materials, and that the

“the balance of circuit court precedent and the purpose of Brady

[v. Maryland]” supported the finding that Nelson could assert

his claim). While the government did not provide extensive

analysis of this argument in its original briefing, a motion for

reconsideration is not the appropriate time to “reargue facts

and theories upon which a court has already ruled,” New York,

880 F. Supp. at 38, to “raise new issues that could have been

raised previously,” Kattan, 995 F.2d at 276, or to otherwise

“re-litigate th[e] issue,” Singh, 383 F. Supp. 2d at 101–102.

In any event, the government’s arguments are unavailing.

The Opinion explicitly analyzed Ruiz and concluded that Ruiz

“did not decide whether a defendant is entitled to exculpatory

evidence at the guilty plea stage.” Nelson, 2013 WL 5778318, at

*3; see also Ruiz, 536 U.S. at 625 (“In this case we primarily

consider whether the Fifth and Sixth Amendment require federal

prosecutors, before entering into a binding plea agreement with

a criminal defendant, to disclose ‘impeachment information
 -8-

relating to any informants or other witnesses.’”); id. at 628

(“The constitutional question concerns a federal criminal

defendant’s waiver of the right to receive from prosecutors

exculpatory impeachment material[.]”). The government contends

that pre-Ruiz cases “are of no assistance in interpreting Ruiz

because the authors of those opinions had no access to the

Supreme Court’s reasoning,” Govt.’s Mot. at 13-14, and that “the

Court’s reliance on the cases it cited was faulty, because of a

flawed understanding of the facts of those cases and of their

precedential value post-Ruiz,” Reply at 11. However, Ruiz did

not abrogate or overrule the pre-Ruiz cases that were considered

in the Opinion. Any reliance on the reasoning of those cases

was appropriate and not a clear legal error. Nelson, 2013 WL

5778318, at *4-5. Further, the government’s argument that “it

is not entirely clear that the rationale of these cases supports

application of Brady v. Maryland with full force in the plea

context,” Govt.’s Mot. at 14, fails to point out any intervening

change of controlling law, new evidence unavailable during the

first disposition, or a clear error or manifest injustice, and

provides no reason to reconsider the Opinion. The government

appears merely to disagree with the analysis of the cases, which

is insufficient to trigger reconsideration. E.g., Singh, 383 F.

Supp. 2d at 102 (finding reconsideration inappropriate because

the party’s argument that the court has misconstrued case law
 -9-

“has accused the court of an error of reasoning, not of

apprehension”).

The government also argues that the Opinion’s conclusion

that “Ruiz drew a significant distinction between impeachment

and exculpatory evidence,” see Nelson, 2013 WL 5778318, at *3,

is flawed. Govt.’s Mot. at 7-8, 10. Again, the government

disagrees with the reasoning of the Opinion, but does not point

out a clear legal error. The Court in Ruiz specifically

discussed impeachment material 1 and its particular value and

relationship to a fair trial; the Ruiz Court did not broadly

1
Indeed, the Court narrowed its holding even further,
stating that “in the context of this agreement, the need for
this information is more closely related to the fairness of a
trial than the voluntariness of the plea.” Ruiz, 536 U.S. at
633 (first emphasis added). If anything, this suggests that,
rather than announcing a categorical rule that the government is
not required to disclose any information pre-plea, an analysis
of the surrounding facts and circumstances, as well as the value
of the information, is required to determine if the failure to
disclose affects the voluntariness of the plea.
This implication is supported by Justice Thomas’
concurrence: “The Court, however, suggests that the
constitutional analysis turns in some part on the ‘degree of
help’ such information would provide to the defendant at the
plea stage, a distinction that is neither necessary nor
accurate.” Ruiz, 536 U.S. at 633 (Thomas, J., concurring in
judgment) (citation omitted). Justice Thomas explicitly stated
that Brady v. Maryland’s purpose was “avoidance of an unfair
trial to the accused” which was “not implicated at the plea
stage” but his opinion was not joined by a single other justice.
Id. (internal quotation marks omitted). The Court’s opinion,
therefore, may suggest that due process requires disclosure of
even affirmative defense information before a guilty plea,
depending on the context of the plea agreement. At the very
least, the Court’s opinion in Ruiz shies away from directly
holding that Brady v. Maryland never applies at the plea stage.
 -10-

discuss exculpatory information. Ruiz, 536 U.S. at 628-30; see

also United States v. Moussaoui, 591 F.3d 263, 286 (4th Cir.

2010) (“To date, the Supreme Court has not addressed the

question of whether the Brady[ v. Maryland] right to exculpatory

information, in contrast to impeachment information, might be

extended to the guilty plea context.”). The Court in Ruiz also

discussed the defendant’s waiver of her right to receive

information pertinent to an affirmative defense. Ruiz, 536 U.S.

at 633. Yet, again, the Court did not broadly state that the

government was not required to disclose any exculpatory

information, opting instead to find that Ruiz’s fast track plea

agreement, which carved out specific types of exculpatory

evidence that would not be disclosed to the defendant, did not

violate due process. Id. (“We do not believe the Constitution

here requires provision of this information to the defendant

prior to plea bargaining[,] for most (though not all) of the

reasons previously stated.” (emphasis added)).

The government further contends that the Supreme Court has

previously rejected any distinctions between impeachment

evidence and exculpatory evidence. Govt.’s Mot. at 10. For

example, the government argues that the Supreme Court in United

States v. Bagley “not[ed] that in the context of the

government’s disclosure obligations, [the] Supreme Court ‘has

rejected any . . . distinction between impeachment evidence and
 -11-

exculpatory evidence.’” Id. (quoting United States v. Bagley,

473 U.S. 667, 676 (1985)). However, the government’s quotation

omits a critical word from the Court’s opinion in Bagley: the

Court “rejected any such distinction between impeachment

evidence and exculpatory evidence.” Bagley, 473 U.S. at 676

(emphasis added). The “any such distinction” referred to the

lower court’s conclusion that omission of impeachment

information mandated an automatic reversal, whereas omission of

exculpatory information did not require automatic reversal. Id.

at 675-77. The Court in Bagley did not categorically reject all

distinctions between exculpatory and impeachment evidence. See

id. And the Court in Ruiz used the terms “exculpatory” and

“impeachment” separately, rather than as identical terms. Ruiz,

536 U.S. at 631 (discussing the “trial-related rights to

exculpatory and impeachment information in Brady[ v. Maryland]

and Giglio”). The Court has not treated exculpatory evidence

and impeachment information as indistinguishable, and Ruiz does

not foreclose a Brady v. Maryland violation from being the basis

of a claim that a guilty plea is involuntary. 2 Because Ruiz does

2
Additionally, the concerns that animated the Court’s
decision in Ruiz are not applicable here, and due process favors
allowing Nelson to assert his claim. The harm that could result
from the government disclosing the 1:44 p.m. e-mail does not
rise to the level of harm that the Supreme Court found in Ruiz.
See Ruiz, 536 U.S. at 631-32. The 1:44 p.m. e-mail does not
expose any witnesses to harm, nor would it disrupt any
investigations. In fact, the government largely made the
 -12-

disclosures that Nelson wanted in this case, but omitted the
1:44 p.m. e-mail. That the government in fact already disclosed
the e-mail chain -- albeit, incompletely -- cuts against its
argument that this ruling could have a “particularly onerous”
burden on the government, as does the government’s
mischaracterization of the completeness of the discovery packet.
Moreover, the government should be obligated to speak correctly
when affirmatively stating what evidence it does and does not
have, or what evidence does or does not exist.
Further, due process considerations favor permitting using
this particular Brady v. Maryland claim as the foundation of an
attack on the voluntariness of Nelson’s guilty plea. While the
Court in Ruiz found that a “right” to general disclosure of
material impeachment information had “limited” value, the same
cannot be said of the omitted exculpatory information at issue
here. See id. at 629-30. The government did not merely fail to
disclose Brady v. Maryland materials, but in fact concealed by
its affirmative misrepresentation, Brady v. Maryland materials.
The value of this additional safeguard to protect defendants
from affirmative misrepresentations before a plea is entered was
discussed in the Opinion, see Nelson, 2013 WL 5778318, at *5
(“[P]recluding a defendant from raising such a Brady[ v.
Maryland] claim after a guilty plea could create a risk too
costly to the integrity of the system of justice to
countenance.”), and as is discussed above, there are few adverse
impacts to permitting Nelson to advance his claim.

However important plea bargaining may be in the
administration of criminal justice, our opinions have
established that a guilty plea is a serious and
sobering occasion inasmuch as it constitutes a waiver
of the fundamental rights to a jury trial, to confront
one’s accusers, to present witnesses in one’s defense,
to remain silent, and to be convicted beyond all
reasonable doubt. Since Kercheval v. United States,
274 U.S. 220 (1927), this Court has recognized that
“unfairly obtained” guilty pleas in the federal courts
ought to be vacated.

Santobello v. New York, 404 U.S. 257, 264 (1971) (Douglas, J.,
concurring) (citations omitted). This affirmative
misrepresentation frustrated due process, undermined the
voluntariness of Nelson’s guilty plea, and led to a guilty plea
that was “unfairly obtained.” See id.
Moreover, even if the Court in Ruiz distinguished between
evidence about the defendant’s factual innocence and other
 -13-

not bar a Brady v. Maryland violation from being the premise of

Nelson’s claim, there is no clear legal error that merits

reconsideration.

II. SUPPRESSED EVIDENCE

The government revives its original argument that Nelson

“actually possessed the non-disclosed information” and thus it

could not suppress the evidence. Govt.’s Mot. at 21-22

(emphasis omitted). The Opinion rejected this argument, and

concluded that “[t]he government cannot claim its Brady[ v.

Maryland] obligation had been discharged since Nelson did not

know that the government had the 1:44 p.m. e-mail” and that

“[t]he government nonetheless was obligated to disclose the e-

mail because Brady[ v. Maryland] requires disclosure of all

exculpatory material.” Nelson, 2013 WL 5778318, at *7. “A

court may properly exercise its discretion by denying a motion

for reconsideration that ‘raise[s] . . . arguments for

reconsideration that the court ha[s] . . . already rejected on

the merits.” McLaughlin v. Holder, 864 F. Supp. 2d 134, 141

exculpatory information, such as information relevant to an
affirmative defense, that makes no difference here. The
1:44 p.m. e-mail is not merely impeachment material or proof of
an affirmative defense, but goes to directly to Nelson’s intent,
which is an element of the crime of which he was convicted.
While not dispositive, such information “demonstrate[s] actual
factual innocence of the offense of conviction; i.e., that
petitioner did not commit the crime of which he was convicted.”
United States v. Mikalajunas, 186 F.3d 490, 494 (4th Cir. 1999).
 -14-

(D.D.C. 2012) (quoting Capitol Sprinkler Inspection, Inc. v.

Guest Servs., Inc., 630 F.3d 217, 227 (D.C. Cir. 2011)).

As is discussed in the Opinion, to establish a Brady v.

Maryland claim, the defendant must initially show that the

government possessed material favorable to the defense that the

government did not disclose. United States v. Price, 566 F.3d

900, 910 (9th Cir. 2009). Nelson indisputably established that

the government possessed the 1:44 p.m. e-mail, and the

government concedes that it did not disclose that evidence.

Once the defendant has met this burden, then the government must

show that “the prosecutor satisfied his duty to disclose all

favorable evidence known to him.” Id. The government does not

disclaim knowledge that it possessed the 1:44 p.m. e-mail.

Therefore, as a Brady v. Maryland disclosure matter, the

government was required to disclose the e-mail unless it can

show that Nelson knew “of the specific exculpatory information.”

United States v. Clarke, 767 F. Supp. 2d 12, 52 (D.D.C. 2011);

United States v. Derr, 990 F.2d 1330, 1335 (D.C. Cir. 1993)

(“Brady[ v. Maryland] only requires disclosure of information

unknown to the defendant . . . .”). This is where the

government failed. The record showed that Nelson’s former

defense counsel was unaware of the 1:44 p.m. e-mail, that

“Nelson did not recall the specific e-mail, or, more

importantly, know that it was missing from the discovery packet
 -15-

that the government disclosed to his counsel,” and that the

government affirmatively represented that it had disclosed all

electronic communications between Nelson and Palchak. 3 See

Nelson, 2013 WL 5778318, at *7. The government’s argument that

it discharged its duty to disclose Brady v. Maryland materials

because Nelson possessed the 1:44 p.m. e-mail -- despite the

government’s misrepresentation that it had disclosed the entire

e-mail chain -- was explicitly rejected. See Nelson, 2013 WL

5778318, at *7 (citing United States v. Johnson, 592 F.3d 164,

171-72 (D.C. Cir. 2010); Clarke, 767 F. Supp. 2d at 52). This

was not a case in which a defendant with “knowledge of the

government’s possession of possibly exculpatory information

. . . sit[s] on [his] hands until after a guilty verdict is

returned[,]” Derr, 990 F.2d at 1335, but rather a case in which

the government, even if inadvertently, falsely represented that

it was disclosing all of the electronic communications between

the defendant and an officer. Nelson, 2013 WL 5778318, at *6-7.

The government’s attempt to shift the burden of bearing the

consequences of its misrepresentation to the defendant was

squarely rejected, and the Opinion concluded that Nelson’s

3
The government argues that the reasonableness of counsel’s
reliance on the government’s misrepresentation requires an
evidentiary hearing. Govt.’s Mot. at 23-24. However, the
reasonableness of counsel’s reliance was not dispositive when
the Opinion issued and is not dispositive now, and does not
require a hearing.
 -16-

guilty plea did not immunize the government from the

ramifications of that false representation. See id. Rather,

the Opinion found that the government could not escape its

obligation to disclose Brady v. Maryland materials by furnishing

an incomplete discovery packet when it specifically represented

the packet as complete. See id. Thus, as is discussed below,

even if the government does not always have an obligation to

disclose Brady v. Maryland materials, the facts of this case

compel the conclusion that the government’s misrepresentation

improperly suppressed exculpatory materials, and such an act

under any fair test cannot support the voluntariness of a guilty

plea.

Whether the government’s affirmative misrepresentation is

also relevant to Nelson’s ineffective assistance of counsel

claim has no bearing on the government’s obligation to disclose

under Brady v. Maryland. The government’s motion for

reconsideration does not offer any intervening case law calling

this conclusion into question, nor does it point to any binding

case law that was not considered. Thus, there is no clear legal

error, and the government’s motion provides no reason to

reconsider this aspect of the Opinion. 4

4
The government also argues that “the Court erred in the
application of” the Brady v. Maryland standard. Govt.’s Mot. at
32. As this argument reiterates the government’s prejudice
arguments raised in its original briefing, see id. at 33-35
 -17-

III. PREJUDICE

Despite analyzing Nelson’s claim under Brady v. Maryland in

its original briefings, the government now argues that the

proper standard to use to assess prejudice is Brady v. United

States, which governs the voluntariness of guilty pleas, rather

than Brady v. Maryland, which governs claims involving the

government’s non-disclosure of favorable and material evidence. 5

The government appears to be arguing that the Brady v.

United States framework should be used in lieu of the prejudice

inquiry under Brady v. Maryland. See Govt.’s Mot. at 3, 27-28.

(reiterating points that the government had “pointed out in its
Supplemental Memorandum”), the government’s motion on this
ground will be denied. See McLaughlin, 864 F. Supp. 2d at 141.
5
In Brady v. Maryland, the Court held that “the suppression
by the prosecution of evidence favorable to an accused upon
request violates due process where the evidence is material
either to guilt or to punishment, irrespective of the good faith
or bad faith of the prosecution.” 373 U.S. at 97. To establish
a Brady v. Maryland violation, the defendant must show that
there was (1) favorable evidence (2) that was suppressed by the
State and (3) prejudice ensued. See id.; Strickler v. Greene,
527 U.S. 263, 281-82 (1999).
On the other hand, in Brady v. United States, the Court
found that “[w]aivers of constitutional rights not only must be
voluntary but must be knowing, intelligent acts done with
sufficient awareness of the relevant circumstances and likely
consequences.” 397 U.S. at 748. For a guilty plea to be
constitutionally valid under Brady v. United States, the guilty
plea must be “‘a voluntary and intelligent choice among the
alternative courses of action open to the defendant.’” United
States v. McCoy, 215 F.3d 102, 107 (D.C. Cir. 2000) (quoting
Hill v. Lockhart, 474 U.S. 52, 56 (1985)). A plea cannot be
voluntary “‘if it is induced by threats or misrepresentation.’”
United States v. Mathis, 963 F.2d 399, 410 (D.C. Cir. 1992)
(quoting United States v. Russell, 686 F.2d 35, 38 (D.C. Cir.
1982)).
 -18-

It is not clear why the Brady v. United States inquiry should

replace the prejudice inquiry under Brady v. Maryland. The

government does not offer any binding case law holding that when

a defendant seeks to withdraw his plea based on a Brady v.

Maryland violation, the court must assess the claim under Brady

v. United States either in place of Brady v. Maryland’s

prejudice inquiry or in addition to it. The government offers

only a discussion of the differences between the two standards

and a citation to a First Circuit case. See Govt.’s Mot. at 28-

30 (citing Ferrara v. United States, 456 F.3d 278 (1st Cir.

2006)). However, in Ferrara, the First Circuit did not decide

which framework to use in deciding whether the defendant could

withdraw his guilty plea. See id. at 290. Instead, the First

Circuit found that it was unnecessary to resolve the Brady v.

Maryland question because there was a clear due process

violation under Brady v. United States. Id.

The Supreme Court has not assessed all requests to withdraw

guilty pleas under the Brady v. United States framework. For

example, when faced with an ineffective assistance of counsel

claim, the Court has used the framework articulated in

Strickland v. Washington, 466 U.S. 668 (1984), rather than using

Brady v. United States. E.g., Hill v. Lockhart, 474 U.S. 52

(1985). The government offers no reason to proceed under the

general Brady v. United States framework rather than under the
 -19-

specific framework that governs the constitutional violation

Nelson complains of, nor does the government offer case law

requiring that the court consider the factors identified by the

government as relevant to the Brady v. United States inquiry.

Govt.’s Mot. at 17. The government also provides no reason to

combine the two inquiries. Thus, there is no clear legal error

here in assessing Nelson’s claim using the Brady v. Maryland

framework as opposed to the Brady v. United States framework. 6

Importantly, the government acknowledges that it “did not

offer the Brady v. United States analysis in its initial

pleading or at oral argument.” Reply at 18. The government

instead argues that its “choice not to emphasize earlier the

significance of [Brady v. United States] does not negate the

importance of that decision to the issues before the Court.”

Reply at 18 n.16. However, “a losing party may not use a Rule

59 motion to raise new issues that could have been raised

previously.” Kattan, 995 F.2d at 276. “Rule 59(e) motions are

aimed at reconsideration, not initial consideration.” GSS Grp.

Ltd. v. Nat’l Port Auth., 680 F.3d 805, 812 (D.C. Cir. 2012)

(internal quotation marks omitted); see also Kattan, 995 F.2d at

6
At best, a court should determine if there was a Brady v.
Maryland violation -- an inquiry that would include the
prejudice analysis -- then proceed to the separate inquiry under
Brady v. United States to determine if the plea was nonetheless
voluntary. As is discussed below, a subsequent Brady v. United
States inquiry results in the same outcome here.
 -20-

276 (affirming the district court’s finding of waiver because

the party did not raise the argument before judgment). The

government in its opening brief offered only a short paragraph

in its “Governing Legal Principles” section stating that a

defendant may not withdraw a plea unless he can “‘show that the

plea proceeding was tainted by a fundamental defect which

inherently results in a complete miscarriage of justice or an

omission inconsistent with the rudimentary demands of fair

procedure.’” Govt.’s Brady Opp’n at 8 (quoting United States v.

Farley, 72 F.3d 158, 162 (D.C. Cir. 1995)). The government did

not analyze the facts under that standard, or even mention the

guilty plea standard in its “Argument” section. See id. at 11-

16; see also Govt.’s Supp. Brady Mem. (omitting a discussion of

the Brady v. United States standard). Accordingly, the

government has waived its argument that Nelson’s claim should be

assessed under Brady v. United States rather than Brady v.

Maryland. E.g., Kattan, 995 F.2d at 276; cf. Wash. Legal Clinic

for the Homeless v. Barry, 107 F.3d 32, 39 (D.C. Cir. 1997)

(declining to resolve an issue raised by the party in “a cursory

fashion” with “only bare-bones arguments”).

In any case, the analysis under Brady v. United States

would result here in the same conclusion. 7 Certainly, the

7
The government argues that “consideration of the complete
range of factors relevant to the determination of whether
 -21-

Nelson’s plea was voluntary . . . compels the conclusion that
Nelson’s plea was voluntary, and should be reinstated.” Reply
at 19. The government argues that “[t]his Court bypassed
consideration of these factors and linked its materiality
determination only to an assessment of how much ‘probative
force’ the 1:44 p.m. e-mail would have added to a potential
methamphetamine addict defense.” Govt.’s Mot. at 30. The
government did not provide any legal authority requiring courts
in the D.C. Circuit to assess any particular factors in
determining whether a guilty plea is voluntary. Nor has the
First Circuit said that the factors identified by the government
are mandatory. Ferrara, 456 F.3d at 294 (recognizing that
“[w]hile this checklist is useful, experience teaches that each
defendant’s decision as to whether or not to enter a guilty plea
is personal, and thus, unique. Consequently, the compendium of
relevant factors and the comparative weight given to each will
vary from case to case. The ultimate aim, common to every case,
is to ascertain whether the totality of the circumstances
discloses a reasonable probability that the defendant would not
have pleaded guilty absent the misconduct.”). Nelson’s early
admission of guilt and acceptance of responsibility weighs in
favor of finding that his plea of guilty was voluntary.
Nevertheless, if such a consideration were dispositive,
defendants might never be permitted to withdraw their guilty
pleas. Thus, even though some of the factors, such as Nelson’s
plea of guilty and the fact that he was subject to a higher
penalty had he not pled, might weigh in favor of concluding that
his guilty plea was voluntary, the relevant circumstances --
such as the government’s misrepresentation, the weight and value
of the undisclosed evidence and its impact on the factual basis
for the plea, and Nelson’s early and repeated assertion that he
was meeting Palchak only to acquire methamphetamines, see
Nelson’s § 2255 Mot., Nelson Decl. at ¶¶ 17-18, 20 (discussing
Nelson’s conversations with his counsel about his reasons for
meeting Palchak in D.C.) -- sufficiently “undermine[] confidence
in the voluntariness of Nelson’s plea[,]” Nelson, 2013 WL
5778318, at *8 n.9 (internal quotation marks omitted), to
conclude that Nelson would not have pled guilty but for the
government’s misconduct. See also Miller v. Angliker, 848 F.2d
1312, 1322 (explaining that though the test is an objective one,
“even where counsel would likely adhere to his recommendation of
a plea of guilty or not guilty . . . , if there is a reasonable
probability that but for the withholding of the information the
accused would not have entered the recommended plea but would
have insisted on going to a full trial, the withheld information
 -22-

government is correct that Nelson’s guilty plea is not invalid

merely because it was motivated by his desire to accept the

probability of a lesser penalty. See Brady v. United States,

397 U.S. at 747. A plea, however, can be rendered legally

involuntary by government misrepresentation. See id. at 755-56;

United States v. Pollard, 959 F.2d 1011, 1021 (D.C. Cir. 1992)

(“Only physical harm, threats of harassment, misrepresentation,

or promises that are by their nature improper as having no

proper relationship to the prosecutor’s business (e.g., bribes)

render a guilty plea legally involuntary.” (internal quotation

marks omitted)).

Here, the government concedes that it misrepresented the

completeness of the discovery packet. Nelson, 2013 WL 5778318,

at *7. The government, however, argues that there must be

intentional or knowing “egregiously impermissible conduct” to

support a claim that the defendant’s guilty plea is involuntary.

See Govt.’s Mot. at 28; Reply at 15-16 n.14. Yet, the

government provides no legal authority supporting this

distinction, or defining “egregiously impermissible conduct” as

intentional or bad faith conduct. Rather, as the First Circuit

explained in Correale v. United States, where the defendant

is material within the meaning of the Brady v. Maryland line of
cases”).
 -23-

argued that his plea was involuntary because the prosecution

promised to make a recommendation of an illegal sentence:

Nor are the obligations to avoid misrepresentations or
improper promises limited to good faith efforts.
Prosecutorial duties affecting the fairness of trials
have never been so restricted. The same is true of
the government’s role in plea bargaining. In Von
Moltke v. Gillies, 332 U.S. 708 (1948), a majority of
the Court agreed that the guilty plea there would be
void if “a member of the prosecution, gave her,
however honestly, clearly erroneous legal advice.” In
Santobello, [404 U.S. 257 (1971)], the Court
reaffirmed that view: “That the breach of agreement
was inadvertent does not lessen its impact.”
Prosecutorial misrepresentations, though made in good
faith, even to obtain a just . . . end, are not
acceptable.

479 F.2d 944, 947 (1st Cir. 1973) (footnote and citations

omitted); Briscoe v. United States, 391 F.2d 984 (D.C. Cir.

1968) (“We assume that there was no lack of bona fides on

anyone’s part. This bona fides does not alone negative the

possibility that appellant’s guilty plea may not be fairly

retained.”). The government has offered no legal authority to

the contrary. Thus, the “inadvertence” of the government’s

nondisclosure, and more importantly, of its misrepresentation,

does not change the involuntariness of Nelson’s plea. See

Nelson, 2013 WL 5778318, at *8 (concluding that there was a

“reasonable probability that had the government disclosed the

1:44 p.m. e-mail, Nelson would have taken his chances at

trial[.]”).
 -24-

Ultimately, even if Nelson was not generally entitled to

Brady v. Maryland materials before entering his guilty plea,

once the government represented that it had given Nelson a

complete copy of the e-mail exchange between Nelson and Palchak,

the government was obligated to do so. Cf. United States v.

Russell, 686 F.2d 35, 39 (D.C. Cir. 1982) (“Although it may be

permissible for prosecutors to discuss deportation consequences

with defendants when their understanding of the law is accurate,

the practice cannot be tolerated when the prosecution’s advice

is erroneous, no matter how well intended. The government may

not be required to inform defendants of collateral plea

consequences such as deportation, but it does have an obligation

not to mislead them.” (emphasis added) (citation omitted)),

abrogated on other grounds by Padilla v. Kentucky, 559 U.S. 356

(2010). By failing to disclose all of the materials that the

government represented it did disclose, the government

effectively concealed the omitted material. Cf. Banks v.

Dretke, 540 U.S. 668, 696, 698 (2004) (“A rule thus declaring

‘prosecutor may hide, defendant must seek,’ is not tenable in a

system constitutionally bound to accord defendants due process.

. . . [The defendant] was entitled to treat the prosecutor’s

submissions as truthful.”). The government may not have had the

obligation to speak, but “because the prosecution chose to

speak, and spoke incorrectly[,]” Russell, 686 F.2d at 41, to
 -25-

Nelson’s prejudice, Nelson’s plea cannot be considered

voluntary. See Nelson, 2013 WL 5778318, at *7; see also Banks,

540 U.S. at 698 (“Prosecutors’ dishonest conduct or unwarranted

concealment should attract no judicial approbation.”). Thus,

the government’s affirmative misrepresentation to the defense

warrants allowing Nelson to withdraw his guilty plea.

CONCLUSION AND ORDER

The government has not demonstrated that it is entitled to

relief under Rule 59(e). It has not shown that there was a

clear legal error in the October 25, 2013 Opinion, it waived the

argument that Brady v. United States should govern the analysis,

and, even under Brady v. United States, Nelson’s plea was

involuntary. Accordingly, it is hereby

ORDERED that the government’s motion [60] for

reconsideration be, and hereby is, DENIED. The Clerk is

directed to notify the Court of Appeals promptly of this

disposition.

SIGNED this 11th day of February, 2014.

/s/
RICHARD W. ROBERTS
Chief Judge