United States v. Segarra-Rivera

United States Court of Appeals
For the First Circuit

No. 05-1582

UNITED STATES OF AMERICA,

Appellee,

v.

JUAN SEGARRA-RIVERA,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF PUERTO RICO

[Hon. Salvador E. Casellas, U.S. District Judge]

Before

Selya, Circuit Judge,
Stahl, Senior Circuit Judge,
and Howard, Circuit Judge.

Ignacio Fernández de Lahongrais, by appointment of the court,
for appellant.
Nelson Pérez-Sosa, Assistant United States Attorney (Chief,
Appellate Division), with whom Rosa Emilia Rodríguez-Vélez, United
States Attorney, was on brief, for appellee.

January 11, 2007
 SELYA, Circuit Judge. Defendant-appellant Juan Segarra-

Rivera (Segarra) asks that we remand for an evidentiary hearing on

his asserted right to withdraw his guilty plea. Segarra premises

this entreaty on the ground that he was entitled, under the Sixth

Amendment, to be represented at his plea-withdrawal hearing by

conflict-free counsel. For all practical purposes, that rule is

ironclad; the question here is whether the district court, when

faced with a colorable claim of an actual conflict of interest,

should have invoked that rule. Concluding, as we do, that the

court acted in derogation of Segarra's Sixth Amendment rights by

proceeding as it did, we remand for further factfinding consistent

with this opinion.

We rehearse here only those facts necessary to place this

appeal into perspective. On August 28, 2003, a federal grand jury,

in a superseding indictment, charged Segarra with conspiracy to

distribute multi-kilograms of controlled substances. See 21 U.S.C.

§§ 841(a)(1), 846. The thrust of that count was that Segarra

managed and supervised a booming business in the sale of drugs at

a housing project in Juncos, Puerto Rico. The superseding

indictment also contained a second (derivative) count seeking

criminal forfeiture.

After some preliminary skirmishing, not relevant here,

Segarra pleaded guilty to both counts of the indictment pursuant to

a written plea agreement (the Agreement). See Fed. R. Crim. P.

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11(c)(1)(A)-(B). The instant appeal concerns the circumstances

surrounding Segarra's decision to plead guilty and his subsequent

endeavors to withdraw his guilty plea.

During the relevant time frame, Attorney Rafael Anglada-

López (Anglada) represented Segarra by appointment of the district

court.1 On August 17, 2004, Anglada visited Segarra in prison and

secured his signature on the Agreement. A change-of-plea hearing,

held the next day, proceeded without incident. In pertinent part,

Segarra, through an interpreter, confirmed that he understood both

the nature of the charges and the consequences of confessing guilt

to them. He stated that he had entered into the Agreement of his

own accord and without pressure from anyone; that he had discussed

the terms of the Agreement with his attorney before signing it; and

that he was satisfied with Anglada's representation.

On December 8, 2004, Segarra initiated a series of pro se

motions aimed at vitiating his plea. He claimed that he had not

been fully informed of the consequences of pleading guilty and that

his entry into the Agreement was neither knowing nor voluntary; to

the contrary, he signed the Agreement and responded on cue during

1
Anglada was Segarra's second court-appointed lawyer. He was
appointed on June 15, 2004, after Segarra's original attorney,
Francisco M. Dolz-Sánchez, was permitted to withdraw. In
connection with that switch, Segarra had alleged that Dolz-Sánchez
"wants me to sign an agreement, which in my opinion is unfair,
because I haven't seen the evidence."

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the change-of-plea colloquy only because Anglada had coerced and

manipulated him.

With respect to this last-mentioned claim, Segarra

offered a number of particulars. He asserted, for example, that

Anglada took advantage of his lack of education, his inability to

speak English, and his debilitated physical and mental condition.

He also asserted that, during Anglada's prison visit, the lawyer

had insisted that he would not leave empty-handed but "had to come

away with the [A]greement signed." In order to ensure Segarra's

acquiescence, Anglada ambushed him with a surprise visit from his

wife, Yolanda Vega, whom Segarra had not seen in three months.

Vega, convalescing in a wheelchair, allegedly implored Segarra

through a veil of tears to follow Anglada's lead. Segarra further

noted that Anglada had not performed the rudimentary preparatory

work needed to try the case and, thus, was adamantly unreceptive to

Segarra's insistence on a jury trial. Finally, Segarra charged

that Anglada had concealed exculpatory evidence from the court. As

a result of these foibles, Segarra stated, he signed the Agreement

and went through the change-of-plea colloquy in a state of

confusion.

In response to Segarra's allegations, Anglada filed a

motion requesting an evidentiary hearing on the plea-withdrawal

request. In that motion, Anglada admitted that, after entering the

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plea, Segarra repeatedly beseeched him (Anglada) to move to set it

aside. Anglada had not, however, heeded his client's wishes.

The district court considered Segarra's serial motions on

January 28, 2005 (without convening an evidentiary hearing). At

that time, Segarra submitted a signed statement that a fellow

inmate had helped him draft. That statement reiterated much of

what he had disclosed in his pro se motions, including his claims

that Anglada had concealed exculpatory evidence and manipulated him

into signing the Agreement. In its peroration, Segarra's statement

declared:

I have never accepted the agreement that
counsel Anglada[] made me sign. Counsel
Anglada[] never brought me the evidence in the
case and I always insisted to counsel
Anglada[] on my desire to go to trial.
Counsel Anglada[] merely limited himself to
put "undue pressure" so that I would sign, so
much so that he brought my wife, Yolanda Vega,
in the conditions that I have already reported
. . . .

Segarra also requested that the district court appoint new counsel

to represent him at the plea-withdrawal hearing and thereafter

throughout the case.

Faced with this statement and request, the district court

solicited comments from both the prosecutor and Anglada. The

prosecutor argued that the attempted plea withdrawal constituted no

more than second-guessing sparked by what seemed likely to be a

stiff sentence. For his part, Anglada insisted that he had

explained the Agreement fully to Segarra in Spanish and that

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Segarra had understood him. He maintained that his sole contact

with Vega had been the receipt of desperate telephone calls from

her. He also suggested that video cameras at the prison would bear

out the absurdity of the charge of coercion. While he conceded

that he had been unresponsive to Segarra's persistent instructions

that he seek to vitiate the plea, he explained that he had hoped to

persuade his client not to pursue such a course.

Anglada proceeded to disparage Segarra's stated basis for

retraction of the plea, indicating to the court that Segarra had

understood the nature and consequences of his actions. He even

pointed out that Segarra, in his pro se motions, had failed to

assert his innocence. He then stated cryptically that he wished he

could call Vega and Segarra's brothers as witnesses because they

would "know whether [Segarra] is guilty or not."

In a written rescript, the district court denied

Segarra's motions to withdraw his guilty plea and for new counsel.

See United States v. Segarra-Rivera, Crim. No. 03-188 (D.P.R. Mar.

4, 2005) (unpublished). Following the imposition of a 135-month

incarcerative sentence, Segarra — represented by new counsel —

prosecuted this timely appeal.

The lower court's rescript focused on whether Segarra

should be allowed to withdraw his guilty plea. In our view, this

focus puts the cart before the horse. There is a logically

antecedent question: was Segarra entitled to representation by

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counsel other than Anglada at the plea-withdrawal hearing? If he

was, then his request for the appointment of new counsel should

have been honored — and the failure to honor it would cast doubt

upon the validity of the record on which the district court ruled.

Consequently, we start with this antecedent question.

The Sixth Amendment guarantees that, in all felony cases,

an accused has a right to the assistance of counsel. U.S. Const.

amend. VI. Unless knowingly and intelligently waived, this right

attaches at every critical stage of the criminal process. Iowa v.

Tovar, 541 U.S. 77, 80-81 (2004). The entry of a guilty plea is

one such critical stage, see id. at 81, and a plea-withdrawal

hearing is another, see United States v. Sanchez-Barreto, 93 F.3d

17, 20 (1st Cir. 1996).

Here, Segarra's Sixth Amendment challenge, as presented

to the district court, had two related but conceptually distinct

aspects. One aspect rested upon an argument that counsel performed

ineffectively or incompetently. See, e.g., Strickland v.

Washington, 466 U.S. 668, 687-88 (1984). That aspect is not

pursued on this appeal and, in all events, is not properly before

us. Claims of ineffective assistance of counsel simpliciter,

including claims of substandard performance, are routinely

adjudicated in collateral post-conviction proceedings. See United

States v. Torres-Rosario, 447 F.3d 61, 64 (1st Cir. 2006); see also

28 U.S.C. § 2255. While there are exceptions to this praxis, see,

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e.g., United States v. Theodore, 354 F.3d 1, 3 (1st Cir. 2003);

United States v. Natanel, 938 F.2d 302, 309 (1st Cir. 1991),

Segarra makes no developed argument supporting the applicability of

any such exception here.

The remaining aspect of Segarra's Sixth Amendment

challenge is of a different genre. In mounting this attack,

Segarra does not rely upon allegations of attorney ineffectiveness

or incompetence per se; rather, he maintains that Anglada concealed

exculpatory evidence and manipulated him into signing the Agreement

in order to avoid a trial for which he (the lawyer) had neglected

to prepare. If Segarra's allegations are true — a matter on which

we take no view — then Anglada would have had a very real

incentive, at the plea-withdrawal stage, to cover up his

misconduct. This would mean that Anglada was laboring under an

actual conflict of interest in undertaking to represent Segarra.

See United States v. Burgos-Chaparro, 309 F.3d 50, 52 (1st Cir.

2002) (distinguishing ineffectiveness and conflict of interest

claims). That type of claim, unlike an ineffectiveness claim, is

not routinely relegated to collateral review.2

2
Apart from justiciability concerns, there is another
important distinction between the two types of claims. When a
defendant's claim rests solely on allegations that counsel
performed ineffectively or incompetently, the defendant must also
show prejudice. See Strickland, 466 U.S. at 692-93; Scarpa v.
DuBois, 38 F.3d 1, 8-9 (1st Cir. 1994). When, however, a defendant
makes a timely and colorable showing that his counsel labored under
an actual conflict of interest, he may be entitled to relief
without regard to proof of prejudice. See Cuyler v. Sullivan, 446

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 We add a caveat. Not every bare allegation of a

disagreement between lawyer and client is enough to trigger a right

to new counsel. See, e.g., United States v. Mota-Santana, 391 F.3d

42, 47 (1st Cir. 2004); United States v. Myers, 294 F.3d 203, 206-

08 (1st Cir. 2002). An even smaller subset of such disagreements

will (even arguably) amount to an actual conflict of interest.

Lawyers ordinarily aspire to do their best for clients. Thus, an

"actual conflict," for Sixth Amendment purposes, entails a conflict

of interest sufficient to displace that presumption — one "that

adversely affects counsel's performance." Mickens v. Taylor, 535

U.S. 162, 172 n.5 (2002).3

Here, more than a mere disagreement is at issue.

Segarra's conflict of interest claim was seasonably raised below.

The charge is one of improper and unethical conduct, not merely

professional negligence. And, finally, the record provides enough

indicia of an actual conflict of interest to make the claim

colorable. Hence, the claim warrants review on direct appeal. Cf.

United States v. Colón-Torres, 382 F.3d 76, 84-85 (1st Cir. 2004)

U.S. 335, 349-50 (1980); Torres-Rosario, 447 F.3d at 64.
3
Mickens — a habeas case — narrowed the precedential orbit of
Cuyler v. Sullivan, 446 U.S. 335 (1980), upon which this court,
like many courts of appeals, had relied in resolving conflict of
interest cases. See Mickens, 535 U.S. at 174-75. While this
opinion draws upon principles extracted from pre-Mickens case law,
neither Mickens nor Sullivan is directly applicable.

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(discussing, under the rubric of ineffectiveness, the

appropriateness of direct review of conflict of interest claim).

This brings us to why we believe that Segarra made a

sufficient showing of an actual conflict to render his claim

colorable and justify further inquiry by the district court. He

alleged, with specificity, that Anglada used improper means — for

example, concealing exculpatory evidence from the court,

brainwashing Segarra's ailing wife and bringing her to prison

without any forewarning, and refusing to leave without Segarra's

signature on a pre-prepared agreement — to secure his acquiescence

in a plea he did not want. Segarra describes a motive for the

misconduct — the attorney's eschewal of any semblance of meaningful

trial preparation — that is not implausible on its face. The

indirect evidence, such as the fact that Segarra made his retraction

request soon after the change-of-plea hearing, lends some credence

to the charges. While it may well be that Segarra's accusations

will melt away in the crucible of adversarial testing, we think that

he offered enough to warrant a hearing. Cf. Mota-Santana, 391 F.3d

at 45, 47 (declining to grant relief sought — there, reversal for

district court's refusal to appoint new counsel — upon undeveloped

and purely conclusory accusation that attorney "deceived"

defendant).

The non-evidentiary hearing held by the district court

did not suffice. Segarra's charges, if founded, embody conduct

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different in both kind and degree from a defense attorney's

customary encouragement to his client — even strong encouragement

— to avoid a trial by entering into a negotiated arrangement with

the government. The charges impute to Anglada conduct that is both

improper and unethical.4 An attorney who has committed such

misconduct — and we again emphasize that the alleged misconduct

remains to be proven — would have a very powerful incentive to sweep

it under the rug.

In such a situation, an inevitable tension arises between

advancing the client's interests and preserving the attorney's

reputation (and, perhaps, his livelihood). See Colón-Torres, 382

F.3d at 90; Sanchez-Barreto, 93 F.3d at 21. That tension is enough

to sow the seeds for an actual conflict of interest. See Sanchez-

Barreto, 93 F.3d at 20 (recognizing actual conflict of interest when

"pursuit of a client's interests would lead to evidence of an

attorney's malpractice").

The way in which Anglada responded to Segarra's charges

reinforces our intuition that Anglada could not appropriately

represent Segarra at the plea-withdrawal hearing. Although Anglada

admitted that Segarra had clamored, over and over, to withdraw his

plea, beginning soon after it was entered, he made no effort to

carry out his client's wishes until a frustrated Segarra forced his

4
This, among other things, distinguishes this case from
Torres-Rosario, in which the defendant alleged that the prosecutor
had been guilty of improper conduct. See 447 F.3d at 64-65.

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hand by filing the first of a series of pro se motions with the

district court. Then, at the hearing itself, Anglada opposed

retraction of the plea; attempted to undermine the factual basis on

which the plea-withdrawal request rested; dodged Segarra's charges

of coercion; and went so far as to proffer evidence contradicting

Segarra's version of the relevant events.5 With Anglada so busily

engaged in defending his own integrity and the bona fides of the

plea that he had orchestrated, his interests and Segarra's were

clearly at odds.

The government suggests that the statements made by

Segarra during the change-of-plea hearing undercut his Sixth

Amendment challenge. This suggestion is not frivolous: from time

to time, we have looked to such statements as a basis for denying

plea withdrawals. See, e.g., United States v. Alegria, 192 F.3d

179, 186 (1st Cir. 1999) (explaining that, ordinarily, "a defendant

who asserts a fact in answer to a judge's question during a change-

of-plea proceeding ought to be bound by that answer"). That

principle, however, does not apply in "exceptional circumstances."

Id.

5
We fully appreciate that Anglada may have felt it necessary
to take these steps in order both to defend his own reputation and
to fulfill what he sincerely believed to be his obligations as an
officer of the court. But that is precisely the point: if either
or both of these concerns were paramount, Anglada could hardly be
expected to represent Segarra's interests. A lawyer burdened with
conflicting allegiances to two masters serves neither well.

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 This case potentially fits within that exception. On

Segarra's theory of what transpired, clearly articulated in the

court below, the statements that he made at the change-of-plea

hearing were the product of Anglada's manipulative conduct rather

than proof of the absence of improper manipulation. Given Segarra's

preliminary showing, he was entitled to have that theory advanced

by conflict-free counsel and evaluated by the district court.

The short of it is that the Sixth Amendment entitled

Segarra to the assistance of counsel at his plea-withdrawal hearing.

He did not receive that assistance. Despite having made a timely

request for new counsel and a colorable showing that his then-

attorney was hampered by an actual conflict of interest, Segarra was

left to fend for himself at this critical stage in the proceedings.

That was constitutionally impermissible. See Colón-Torres, 382 F.3d

at 90; Sanchez-Barreto, 93 F.3d at 22. This shortcoming taints the

district court's determination that Segarra failed to adduce

sufficient evidence of manipulation or coercion.

That leaves uncertain the nature of the remedy. In this

instance we choose, in the exercise of our discretion, to leave the

sentence intact and remand to the district court for the appointment

of conflict-free counsel so that the court can hold a full hearing

on Segarra's plea-withdrawal motion.6 If Segarra prevails in that

6
We suggest that the district court may wish to consider
asking Segarra's appellate counsel, who has ably represented him in
this court, to accept that appointment.

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proceeding, the district court should then vacate his sentence,

annul his guilty plea, and conduct such further proceedings as may

be necessary. If, however, the government prevails, the district

court, if requested to do so by Segarra, shall vacate the existing

sentence pro forma and immediately reimpose the same sentence,

thereby giving Segarra an opportunity to appeal the court's denial

of his plea-withdrawal motion.

We need go no further. For the reasons elucidated above,

we remand this matter for further proceedings consistent with this

opinion. We express no opinion as to the outcome of the anticipated

plea-withdrawal hearing.

So Ordered.

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