Toribio Rojas-Medina v. United States of America

United States Court of Appeals
For the First Circuit
No. 18-1150
TORIBIO ROJAS-MEDINA,
Petitioner, Appellant,
v.
UNITED STATES OF AMERICA,
Respondent, Appellee.
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. Francisco A. Besosa, U.S. District Judge]
[Hon. Bruce J. McGiverin, U.S. Magistrate Judge]
Before
Torruella, Selya, and Lynch,
Circuit Judges.
Franco L. Pérez-Redondo, Research & Writing Attorney, with
whom Eric A. Vos, Federal Public Defender, and Vivianne M. Marrero-
Torres, Assistant Federal Public Defender, Supervisor, Appeals
Section, were on brief, for petitioner.
Antonio L. Pérez-Alonso, Assistant United States Attorney,
with whom Rosa Emilia Rodríguez-Vélez, United States Attorney, and
Mariana E. Bauzá-Almonte, Assistant United States Attorney, Chief,
Appellate Division, were on brief, for respondent.
May 16, 2019

-- 1 of 19 --

- 2 -
SELYA, Circuit Judge. In Roe v. Flores-Ortega, 528 U.S.
470 (2000), the Supreme Court held that, as a matter of
constitutional law, a defense attorney has a duty to consult with
a client about an appeal either when a particular defendant
reasonably demonstrated to the attorney that he was interested in
appealing or when the circumstances are such that a rational
defendant would want to appeal. See id. at 480. The Court went
on to hold that when an attorney violates this duty, a presumption
of prejudice arises. See id. at 483. The appeal at hand requires
us, for the first time, to apply the Flores-Ortega presumption of
prejudice in circumstances in which the defendant has previously
executed a plea agreement containing a waiver-of-appeal provision.
Mindful of the teachings of both Flores-Ortega and Garza v. Idaho,
139 S. Ct. 738 (2019), we reverse the district court's dismissal
of petitioner-appellant Toribio Rojas-Medina's petition for post-
conviction relief and direct the district court, on remand, to
afford him an appropriate opportunity to file a timely notice of
appeal.
I. BACKGROUND
The petitioner is a monolingual Spanish speaker who is
a native and citizen of the Dominican Republic. On November 23,
2015, a federal grand jury sitting in the District of Puerto Rico
returned a three-count indictment charging him with unlawfully
transporting noncitizens (count 1), unlawful reentry into the

-- 2 of 19 --

- 3 -
United States by a deported noncitizen (count 2), and failure to
heave to a vessel (count 3). See 8 U.S.C. §§ 1324(a)(1)(A)(i),
1326(b)(1); 18 U.S.C. § 2237(a)(1). Roughly three months later,
the petitioner entered into a plea agreement (the Agreement),
wherein he agreed to plead guilty to count 2 (unlawful reentry
into the United States by a deported noncitizen). In exchange,
the government agreed to dismiss the other two counts. The
Agreement memorialized, inter alia, the parties' stipulation to a
total offense level (TOL) of 21, but contained no stipulation as
to the petitioner's criminal history category (CHC).
In a section of the Agreement entitled "SENTENCING
RECOMMENDATION," the parties agreed that they would "recommend a
sentence at the lower end of the applicable Guideline Sentencing
Range." The parties further agreed that the petitioner "may
request that [his] sentence run concurrently with any pending state
sentence or state revocation sentence that may be imposed as a
result of the current criminal conduct," and "may also argue for
a downward departure" on the basis "that his [CHC] substantially
overrepresent[ed] the seriousness of [his] criminal conduct or the
likelihood that [he] will commit other crimes." Of particular
pertinence for present purposes, the Agreement contained a waiver-
of-appeal provision under which the petitioner surrendered the
right to appeal his conviction and sentence, "provided that [he
was] sentenced in accordance with the terms and conditions set

-- 3 of 19 --

- 4 -
forth in the Sentence Recommendation provisions of [the
Agreement]."
A probation officer prepared the presentence
investigation report (PSI Report). Consistent with the Agreement,
the probation officer recommended a TOL of 21. She assessed the
petitioner eight criminal history points, placing him in CHC IV.
The recommended guideline sentencing range (GSR) was 57 to 71
months.
Neither party objected to the guideline calculations
limned in the PSI Report. The petitioner's then-counsel (whom we
shall call "trial counsel") filed a sentencing memorandum in which
he urged the district court to vary downward and sentence the
petitioner based on a CHC of III. Specifically, trial counsel
sought a sentence of 46 months, which fell at the bottom of the
GSR for a TOL of 21 and a CHC of III. Trial counsel also requested
that the sentence "run concurrently with any pending state
sentence." 1
Prior to sentencing, a different probation officer
approached trial counsel, told him that the PSI Report had
miscalculated the petitioner's CHC, and said that two additional
1 The petitioner committed the current offense while on post-
release supervision in New York. Thus, he was concerned that he
might be subject to additional state prison time if the New York
authorities moved to revoke his supervision due to his federal
offense.

-- 4 of 19 --

- 5 -
criminal history points would be added. These additional points
served to elevate the petitioner from CHC IV to CHC V.
The district court convened the disposition hearing on
May 13, 2016. The court asked trial counsel whether he needed
additional time to prepare, given the change in the probation
officer's CHC calculation. Trial counsel said that he did not
need extra time, reasoning that "by adding two additional points,
it would only strengthen my position as to the overrepresentation
of [the petitioner's] criminal history." He added that he would
still be able to pursue his request for a downward departure. 2 He
then presented his argument for a 46-month sentence. The
government made clear that it was "not objecting or arguing
against" such a sentence, which was "discussed as part of the plea
negotiations." Rather, the government was "standing by the
[Agreement]" and "recommending a sentence at the lower end of the
applicable guideline range based on a [TOL] of 21, according to
the [CHC] that the Court accepts."
2 It is evident that trial counsel was using the term
"departure" colloquially to include both downward departures and
downward variances. Cf. United States v. Santini-Santiago, 846
F.3d 487, 489-90 (1st Cir. 2017) (explaining that departures may
only be "justified by reference to specified characteristics of
the offense or the offender, or to an early disposition program,"
whereas variances may be justified by a much broader swath of
rationales, "such as 'deterrence,' inducing 'respect for the law,'
and effective 'correctional treatment'" (quoting 18 U.S.C.
§ 3553(a))). The word "departure" appears to have been given this
same broad meaning in the Agreement.

-- 5 of 19 --

- 6 -
When all was said and done, the district court adopted
the probation officer's revised recommendation, assessed ten
criminal history points, and placed the petitioner in CHC V. Using
the agreed TOL of 21, the court set the GSR at 70 to 87 months.
It proceeded to impose a 70-month term of immurement to run
consecutively vis-á-vis any state sentence that might be imposed.
Trial counsel immediately objected.
Upon completion of the sentencing proceeding, trial
counsel had a two-minute conversation with the petitioner at the
courthouse cellblock. After this brief chat, the two never spoke
again. Judgment entered on May 13, 2016 — the same day that trial
counsel filed a so-called "Motion to Reconsider Sentence." The
motion papers contended that the 70-month sentence was "extremely
harsh" and "greater than necessary to fulfill the purposes of
sentencing under [18 U.S.C. §] 3553(a)." Three days later, the
district court summarily denied the motion. Trial counsel did not
file a notice of appeal, and the fourteen-day appeal period expired
on May 27, 2016. At that time, the petitioner was not aware that
trial counsel had filed a motion for reconsideration, nor was he
aware that it had been denied.
The petitioner was shuttled among several different
correctional facilities following the imposition of sentence.
After arriving at his destination in mid-July, he wrote to the
district court requesting a copy of his docket sheet. The

-- 6 of 19 --

- 7 -
petitioner stated that he was "in the process of a[n] appeal" and
needed "certain information." The court granted his request on
August 2, 2016. Upon receiving the docket sheet, the petitioner
realized for the first time that a notice of appeal had not been
filed on his behalf. With the help of another inmate, he filed a
pro se petition to vacate his sentence pursuant to 28 U.S.C.
§ 2255, claiming that trial counsel was ineffective for failing to
file a notice of appeal.
The district court referred the section 2255 petition to
a magistrate judge. See 28 U.S.C. § 636(b)(1)(B); Fed. R. Civ. P.
72(b)(1). After appointing post-conviction counsel, the
magistrate judge held an evidentiary hearing. Both the petitioner
and trial counsel testified about the details of their two-minute
cellblock conversation. According to the petitioner, he "asked
the attorney why they had given me so much time" and made it plain
that all along, he had "wanted to appeal because the sentence was
too high." The petitioner testified that trial counsel replied
that the sentence "could not be appealed." When the petitioner
insisted that "there had to be a way," trial counsel advised him
to file a section 2255 petition.
Trial counsel offered a somewhat different version. He
recalled "discussing . . . the changes to the [PSI Report] and why
[the court] finally made the determination that it did." He
thought that he had "mentioned" filing a motion for

-- 7 of 19 --

- 8 -
reconsideration, but he did not "think [he and the petitioner]
ever agreed to it." Importantly, trial counsel claimed to have
told the petitioner that although "there was a waiver of appeal,
. . . if [the petitioner] thought that there was anything that
could be appealed, that he had fourteen days and had to inform me
so that I could file something."
The magistrate judge reserved decision and subsequently
issued a report and recommendation, recommending that the
petitioner's ineffective assistance claim should be granted and
that he should be allowed an appropriate opportunity to perfect a
delayed appeal. The magistrate judge found that although the
petitioner had not explicitly instructed trial counsel to file a
notice of appeal, 3 he had manifestly demonstrated an interest in
appealing sufficient to trigger trial counsel's constitutional
duty to consult. The magistrate judge then concluded that, "[e]ven
fully crediting [trial counsel's] testimony, his discussion with
[the petitioner at the cellblock] still did not meet the Supreme
Court's requirement for a consult." Building on this foundation,
the magistrate judge ruled that the Flores-Ortega presumption of
prejudice, see 528 U.S. at 483, applied even though the petitioner
had signed an appeal waiver. Thus, what remained was "to determine
3 In his appellate briefs, the petitioner does not argue that
he explicitly instructed trial counsel to file a notice of appeal.
Consequently, we deem any such argument waived. See United States
v. Zannino, 895 F.2d 1, 17 (1st Cir. 1990).

-- 8 of 19 --

- 9 -
whether [the petitioner] showed . . . a reasonable probability
that he would have timely appealed." The magistrate judge then
resolved this issue in the petitioner's favor and recommended
granting the section 2255 petition.
The government objected, see Fed. R. Crim. P. 59(b)(2),
and the district court, exercising de novo review, see Fed. R.
Crim. P. 59(b)(3), and without holding a further evidentiary
hearing, rejected the magistrate judge's recommendation. The
court did not take issue with any of the magistrate judge's
findings of fact but, rather, held that Flores-Ortega's
presumption of prejudice was inapposite because the petitioner had
executed an appeal waiver. In the absence of such a presumption,
the petitioner could not (in the district court's view) show any
prejudice flowing from trial counsel's failure to file a timely
notice of appeal. The court acknowledged, though, that if Flores-
Ortega applied notwithstanding the appeal waiver, the petitioner
might be able to demonstrate that he had expressed an interest in
appealing to trial counsel and that trial counsel's failure to
consult with him may have deprived him of an appeal he would
otherwise have taken.
The district court issued a certificate of
appealability, see 28 U.S.C. § 2253(c), and this timely appeal
ensued.

-- 9 of 19 --

- 10 -
II. ANALYSIS
When a habeas petitioner appeals from the district
court's denial of a section 2255 petition for post-conviction
relief following an evidentiary hearing, our review of the court's
factual findings is for clear error. See Casiano-Jiménez v. United
States, 817 F.3d 816, 820 (1st Cir. 2016). Questions of law, of
course, engender de novo review. See id. Here, the magistrate
judge made factual findings after an evidentiary hearing. The
district court — which did not have the benefit of hearing live
testimony — did not take issue with the magistrate judge's factual
findings, nor did it make any explicit factual findings of its
own. Thus, we treat the district court as "adopt[ing] (albeit
implicitly) the well-considered factual findings made by the
Magistrate Judge." United States v. J.C.D., 861 F.3d 1, 5 (1st
Cir. 2017).
Our starting point is the constitutional guarantee of
"the right to the effective assistance of counsel." Strickland v.
Washington, 466 U.S. 668, 686 (1984) (quoting McMann v. Richardson,
397 U.S. 759, 771 n.14 (1970)); see U.S. Const. amend. VI. In
order to succeed on an ineffective assistance claim, a "defendant
must show both that counsel's performance was deficient and that
it prejudiced his defense." Janosky v. St. Amand, 594 F.3d 39, 45
(1st Cir. 2010) (citing Strickland, 466 U.S. at 687). In Flores-
Ortega, the Supreme Court held that Strickland "applies to claims

-- 10 of 19 --

- 11 -
. . . that counsel was constitutionally ineffective for failing to
file a notice of appeal." 528 U.S. at 477.
With respect to the first element of the Strickland
inquiry, the Flores-Ortega Court concluded that a defense
attorney's representation is constitutionally deficient if the
attorney either "disregards specific instructions from the
defendant to file a notice of appeal" or fails (under certain
circumstances) to consult with the defendant about an appeal. Id.
at 480. Specifically, the Court held that "counsel has a
constitutionally imposed duty to consult with the defendant about
an appeal when there is reason to think either (1) that a rational
defendant would want to appeal (for example, because there are
nonfrivolous grounds for appeal), or (2) that this particular
defendant reasonably demonstrated to counsel that he was
interested in appealing." Id. By "consult," the Court clarified
that it meant "advising the defendant about the advantages and
disadvantages of taking an appeal, and making a reasonable effort
to discover the defendant's wishes." Id. at 478.
With respect to the second element of the Strickland
inquiry, the Flores-Ortega Court concluded that a defendant whose
attorney fails to carry out a duty to consult with him about an
appeal is entitled to a presumption of prejudice. See id. at 483.
A defendant is not required to show that an appeal is likely to be
successful in order to be entitled to file an appeal out-of-time

-- 11 of 19 --

- 12 -
based on ineffective assistance of counsel; he need only
demonstrate that "counsel's constitutionally deficient performance
deprive[d] [him] of an appeal that he otherwise would have taken."
Id. at 484.
Until very recently, federal courts were divided as to
whether the Flores-Ortega presumption of prejudice applies when a
defendant has executed an appeal waiver. Compare, e.g., Witthar
v. United States, 793 F.3d 920, 923 (8th Cir. 2015) (holding
Flores-Ortega applicable notwithstanding signed appeal waiver);
Campusano v. United States, 442 F.3d 770, 776-77 (2d Cir. 2006)
(same); Gomez-Diaz v. United States, 433 F.3d 788, 794 (11th Cir.
2005) (same); United States v. Sandoval-Lopez, 409 F.3d 1193, 1198
(9th Cir. 2005) (same), with Nunez v. United States, 546 F.3d 450,
455 (7th Cir. 2008) (holding Flores-Ortega inapplicable because
defendant had signed appeal waiver); United States v. Mabry, 536
F.3d 231, 241 (3d Cir. 2008) (same). But this question, previously
the subject of a circuit split, has now been settled. In Garza,
the Court held four-square that "the presumption of prejudice
recognized in Flores-Ortega applies regardless of whether a
defendant has signed an appeal waiver." 139 S. Ct. at 749. The
Garza Court explained that "while signing an appeal waiver means
giving up some, many, or even most appellate claims, some claims
nevertheless remain." Id. at 745; see United States v. Teeter,
257 F.3d 14, 24-26 (1st Cir. 2001) (explaining that appeal waiver

-- 12 of 19 --

- 13 -
does not apply when waiver's scope was not clearly delineated,
when plea was not knowing and voluntary, or when enforcing waiver
"would work a miscarriage of justice"). The Court stressed that
filing a notice of appeal is "a purely ministerial task that
imposes no great burden on counsel." Garza, 139 S. Ct. at 745
(quoting Flores-Ortega, 528 U.S. at 474).
Although the defendant in Garza — unlike the petitioner
— explicitly instructed his attorney to appeal, we see no reason
why this distinction would affect Garza's holding that the Flores-
Ortega presumption of prejudice "applies regardless of whether a
defendant has signed an appeal waiver." Id. at 749. After all,
Flores-Ortega involved a defendant who had not expressly asked his
attorney to file an appeal. See 528 U.S. at 477. We hold that
Garza applies and, thus, we proceed to analyze the petitioner's
claim under the Flores-Ortega framework.
The first question is whether trial counsel had a duty
to consult with the petitioner. As we already have explained, the
duty to consult is triggered either when "a rational defendant
would want to appeal" or when a "particular defendant reasonably
demonstrated to counsel that he was interested in appealing." Id.
at 480. In this instance, the record makes manifest that the
petitioner expressed to trial counsel an interest in appealing
sufficient to activate trial counsel's duty to consult.

-- 13 of 19 --

- 14 -
We have yet to consider what qualifies as "reasonably
demonstrat[ing]" an interest in appealing. We agree with the
weight of authority, though, that a defendant must have done more
than merely express his displeasure at sentencing. See United
States v. Cong Van Pham, 722 F.3d 320, 325 (5th Cir. 2013); Jackson
v. Att'y Gen. of Nev., 268 F. App'x 615, 620 (9th Cir. 2008).
Instead, the defendant must have "said something to his counsel
indicating that he had an interest in appealing." Cong Van Pham,
722 F.3d at 325 (emphasis in original) (quoting United States v.
Cooper, 617 F.3d 307, 313 (4th Cir. 2010)). A duty to consult
arises, for example, "when . . . a defendant who received
consecutive sentences asked 'about having time run together,'" id.
(quoting Frazer v. South Carolina, 430 F.3d 696, 702, 712 (4th
Cir. 2005)), or "when a defendant asked after sentencing 'what's
next? What can we do now?,'" id. (quoting Palacios v. United
States, 453 F. App'x 887, 889 (11th Cir. 2011) (per curiam)).
Here, the magistrate judge credited the petitioner's
testimony that he asked trial counsel why he had gotten "so much
time." In addition, it is undisputed that the petitioner and trial
counsel discussed the possibility of filing a motion for
reconsideration. The government argues that a motion for
reconsideration and an appeal are materially different. This
argument is unavailing.

-- 14 of 19 --

- 15 -
To begin, "[t]here is simply no such thing as a 'motion
to reconsider' an otherwise final sentence." United States v.
Ortiz, 741 F.3d 288, 292 n.2 (1st Cir. 2014). In other words, the
only vehicle for post-conviction relief that trial counsel
discussed with the petitioner did not actually exist — yet the
petitioner had no way of knowing that. Unsurprisingly, then — as
the district court noted — the petitioner's testimony at the
evidentiary hearing "exhibited confusion" and "conflate[d] a
notice of appeal with a motion for reconsideration." Rojas-Medina
v. United States, 290 F. Supp. 3d 145, 156-57 (D.P.R. 2018). A
defendant — especially a defendant who is not an English speaker
— should not be required to use magic words in order to trigger
his counsel's duty to advise him about his right to appeal. See
Cong Van Pham, 722 F.3d at 325. What counts is the substance and
thrust of what the defendant says to counsel.
In the case at hand, the petitioner made it luminously
clear that he was dissatisfied with the sentence imposed and
interested in whatever relief might be available. No more was
exigible to ground the conclusion that the petitioner reasonably
demonstrated to his lawyer his interest in appealing, thus
triggering the lawyer's duty to consult with him about the
advantages and disadvantages of taking an appeal.
A question remains as to whether trial counsel fulfilled
his duty to consult. We think not. Trial counsel's two-minute

-- 15 of 19 --

- 16 -
chat with the petitioner, without more, was insufficient to
discharge this duty. At a minimum, trial counsel was required to
advise his client about the pros and cons of taking an appeal, and
then to make a reasonable effort to ascertain his client's wishes.
See Flores-Ortega, 528 U.S. at 478. Even if we were to credit
trial counsel's testimony that he told the petitioner that "if he
thought . . . there was anything that could be appealed . . . he
had fourteen days" within which to inform trial counsel that he
wanted to appeal — a matter on which we take no view — that
statement did not shed any glimmer of light on the advantages or
disadvantages of taking an appeal.
In an attempt to sidestep this hurdle, the government
points to conversations between the petitioner and trial counsel
prior to sentencing, in which trial counsel "advised [the
petitioner] about the consequences of his appellate waiver." The
government asserts that, examining the totality of the
circumstances (including these pre-sentencing conversations),
"[trial counsel] did more than enough to effectively 'consult'
with [the petitioner] about an appeal."
This assertion defies reason. Even if we were disposed
to consider the pre-sentencing conversations, it appears that
trial counsel did no more than inform the petitioner that his
appeal waiver would prevent him from filing an appeal. That may
or may not have been true. See Teeter, 257 F.3d at 24-26

-- 16 of 19 --

- 17 -
(cataloguing exceptions to appeal waiver's preclusive effect). In
all events, we agree with the Fifth Circuit that "[c]ounsel's duty
to [consult] requires more than simply notice that an appeal is
available or advice that an appeal may be unavailing." White v.
Johnson, 180 F.3d 648, 652 (5th Cir. 1999).
Our inquiry does not end with the conclusion that trial
counsel did not properly discharge his duty to consult. It remains
for us to determine whether counsel's constitutionally deficient
performance prejudiced the petitioner by "depriv[ing] [him] of an
appeal that he otherwise would have taken." Flores-Ortega, 528
U.S. at 484. The Supreme Court has cautioned that although this
question ultimately "will turn on the facts of the particular
case[,] . . . evidence that there were nonfrivolous grounds for
appeal or that the defendant promptly expressed a desire to appeal
will often be highly relevant in making this determination." Id.
at 472.
Here, the petitioner promptly expressed a desire to
appeal. At his first possible opportunity to speak with counsel
after sentencing, he expressed dissatisfaction with his sentence
and an interest in pursuing post-conviction relief. He then
requested his docket sheet from the district court soon after
arriving at his designated custodial facility. Upon realizing
that no appeal had been taken, he promptly sought assistance and
perfected a section 2255 petition. Cf. Frazer, 430 F.3d at 712

-- 17 of 19 --

- 18 -
(noting that petitioner's "tenacity in pursuing habeas relief
. . . bolsters th[e] conclusion" that he would have appealed).
To cinch the matter, we find that the petitioner has at
least one nonfrivolous ground for appealing, notwithstanding his
appeal waiver. He has made it pellucid that he wishes to
challenge, inter alia, the district court's determination that his
sentence should run consecutive to, not concurrent with, any state
sentence. In United States v. Maldonado-Escarfullery, we held
that an appeal of a consecutive sentence fell beyond the reach of
an appeal waiver when "the plea agreement did not make any
recommendation as to whether the sentence should run concurrently
or consecutively." 689 F.3d 94, 97 n.2 (1st Cir. 2012). Several
years later, we reached the same conclusion in United States v.
Santiago-Burgos, 750 F.3d 19, 23 (1st Cir. 2014).
The petitioner has a plausible argument that the same is
true here. The SENTENCING RECOMMENDATION provision in his case
did not specify whether his sentence should run concurrently or
consecutively, yet the district court chose the latter. It follows
that the petitioner's proposed challenge to the district court's
refusal to run his sentence concurrently with any state sentence
that might be imposed constitutes a nonfrivolous ground of appeal.
After all, an argument need only be colorable to qualify as
nonfrivolous, see United States v. Aguilera, 179 F.3d 604, 607
(8th Cir. 1999); it does not have to be a sure winner.

-- 18 of 19 --

- 19 -
To say more would be superogatory. We hold that trial
counsel's failure to consult deprived the petitioner of an appeal
that he otherwise would have taken.
III. CONCLUSION
We need go no further. For the reasons elucidated above,
we reverse the judgment of the district court and remand with
instructions to vacate the judgment in the underlying criminal
case and reenter it so that the petitioner may enjoy a fair
opportunity to file a timely notice of appeal. For these purposes,
the district court shall follow the procedural roadmap charted by
this court in United States v. Torres-Otero, 232 F.3d 24, 31-32
(1st Cir. 2000). Mandate shall issue forthwith; without prejudice,
however, to the right of either party to file, within customary
time limits, petitions for rehearing or rehearing en banc.

-- 19 of 19 --