United States v. Diaz-Rosado

United States Court of Appeals
For the First Circuit

No. 16-1551

UNITED STATES OF AMERICA,

Appellee,

v.

JOSÉ R. DÍAZ-ROSADO,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO

[Hon. Francisco A. Besosa, U.S. District Judge]

Before

Torruella, Lipez, and Barron,
Circuit Judges.

Richard C. Klugh on brief for appellant.
John A. Mathews II, Assistant United States Attorney, Rosa
Emilia Rodríguez-Vélez, United States Attorney, and Mariana E.
Bauzá-Almonte, Assistant United States Attorney, Chief, Appellate
Division, on brief for appellee.

May 16, 2017
 BARRON, Circuit Judge. On August 15, 2013, José Díaz-

Rosado ("Díaz") was indicted in the United States District Court

for the Southern District of Florida for his role in planning and

organizing a maritime smuggling operation involving over 1,000

kilograms of cocaine. Five days later, Díaz was indicted

again -- this time, in the United States District Court for the

District of Puerto Rico -- for his role in planning and organizing

a maritime smuggling operation involving over 1,000 kilograms of

cocaine. Díaz contends that the Double Jeopardy Clause of the

United States Constitution bars his prosecution on the Puerto Rico

charges because the Florida charges already encompass the conduct

for which he was indicted in Puerto Rico. For the reasons set

forth below, we reject this challenge and affirm the decision of

the District Court to deny Díaz's motion to dismiss the Puerto

Rico indictment on double jeopardy grounds.

I.

Because Díaz's double jeopardy challenge to the Puerto

Rico indictment hinges in part on the procedural history of the

Florida case, we first need to describe the two indictments and

their subsequent travel in some detail. We will then be well

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positioned to explain why we are unpersuaded that the Puerto Rico

indictment must be dismissed on double jeopardy grounds.

A.

On August 6, 2012, federal agents intercepted a vessel

carrying approximately 1,032 kilograms of cocaine off the coast of

Guayama, Puerto Rico.1 The vessel was registered to Díaz, who had

rented a dock for it in Fajardo, Puerto Rico. The government later

determined that Díaz also hired the vessel's two-man crew: Jorge

Suárez-Albelo and Joel Perpiña-Quiles. Although Díaz was not on

board at the time of its seizure, he and another individual were

responsible for following behind the vessel in a separate boat.

Roughly five months later, on December 30, 2012, federal

authorities intercepted a second vessel off the coast of St. Croix,

United States Virgin Islands -- this one carrying approximately

1,157 kilograms of cocaine. This vessel had a different two-man

crew: José De León and Wilson Concepción. Díaz had purchased this

second vessel. He also had directed an associate -- who later

became a confidential source of the Broward County, Florida,

Sherriff's Office -- to purchase two outboard motors for it.

The December seizure formed the basis for a one-count

indictment filed against Díaz in the United States District Court

1 We recite these uncontested facts as laid out in the
Magistrate Judge's report and recommendation, the pre-sentence
report accompanying Díaz's Florida guilty plea, and the
prosecutor's statements at Díaz's change-of-plea hearing.

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for the Southern District of Florida on August 15, 2013. Díaz was

charged with one count of conspiracy to possess with intent to

distribute five kilograms or more of cocaine, in violation of 21

U.S.C. §§ 846 and 841(b)(1)(A)(ii). Díaz pleaded guilty several

months later.

During sentencing, the Florida district court relied on

both the August and December seizures as evidence that Díaz was

responsible for trafficking 2,189 kilograms of cocaine. The

Florida district court also applied a four-level sentencing

enhancement under § 3B1.1(a) of the United States Sentencing

Guidelines for acting as the organizer or leader of a criminal

activity involving five or more participants, and a two-level

sentencing enhancement under § 3C1.1 of the Guidelines for

obstruction of justice for encouraging the confidential source to

lie to government investigators. Díaz was initially sentenced to

life in prison.

Five days after Díaz was indicted in Florida, the

government filed a two-count indictment against him in the United

States District Court for the District of Puerto Rico. Based on

the August seizure, the Puerto Rico indictment charged Díaz with

one count of conspiracy to import more than five kilograms of

cocaine into the United States, in violation of 21 U.S.C. §§ 952,

960, and 963, and one count of conspiracy to possess with intent

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to distribute five kilograms or more of cocaine, in violation of

21 U.S.C. §§ 846 and 841(b)(1)(A)(ii).

Díaz moved to dismiss the Puerto Rico indictment the

same day he entered his plea of guilty in the Florida case. Díaz

contended that the conduct charged in the Puerto Rico indictment

-- in particular, Díaz's participation in the events leading up to

the August seizure -- had already been charged in the Florida case

and thus that dismissal of the Puerto Rico indictment was required

by the Fifth Amendment's Double Jeopardy Clause.

The District Court did not rule on that motion right

away. Instead, the District Court held that motion in abeyance

pending the resolution of the Florida proceedings.

With the Puerto Rico case on hold, Díaz pursued an appeal

of his sentence in the Florida proceedings to the Eleventh Circuit.

In that appeal, he contended, among other things, that the Florida

district court erred in applying the four-level leadership

enhancement, and in failing to apply a two-level downward

adjustment for acceptance of responsibility, pursuant to § 3E1.1

of the Guidelines. United States v. Díaz-Rosado, 615 Fed. Appx.

569, 572 (11th Cir. 2015).

On June 25, 2015, the Eleventh Circuit vacated and

remanded the sentence. Id. at 569. That court concluded, first,

that "no evidence was provided to support [Díaz's] leadership role

with respect to the four crewmen" -- Suárez, Perpiña, De León, and

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Concepción -- and second, that the confidential source could not

be "considered a participant." Id. at 579. On this basis, the

Eleventh Circuit then remanded the case to the Florida district

court for reconsideration of its decision to apply the leadership

enhancement, directing the district court also to reconsider its

decision not to apply the downward adjustment for acceptance of

responsibility. Id. at 581. Upon remand, Díaz was sentenced on

February 18, 2016 to 240 months of imprisonment.2

B.

Several days later, the proceedings in the federal

district court in Puerto Rico resumed. The District Court referred

the motion to dismiss the indictment to a magistrate judge. The

Magistrate Judge issued a report and recommendation recommending

2 The Eleventh Circuit upheld the Florida district court in
two other respects. First, Díaz-Rosado held that the District
Court did not plainly err in finding that there was a factual basis
for the plea. 615 Fed. Appx. at 573-74. Second, Díaz-Rosado held
that the Florida district court adequately explained the charges
against Díaz and thus did not plainly err during the plea colloquy.
Id. at 574-75. On remand, the parties agreed that Díaz was
eligible for a two-level downward adjustment pursuant to the so-
called "safety-valve" provisions laid out in 18 U.S.C. § 3553(f),
and §§ 2D1.1(b)(17) and 5C1.2 of the Guidelines. In sentencing
Díaz a second time, the Florida district court did not apply the
four-level leadership enhancement, nor did it apply the two-level
downward adjustment for acceptance of responsibility.

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that the District Court deny Díaz's motion to dismiss on April 5,

2016.

The Magistrate Judge found as follows. With respect to

Count One of the Puerto Rico indictment, the Magistrate Judge first

noted that the offense charged therein was not an offense charged

in the Florida case. Accordingly, citing United States v. Ortiz-

Alarcon, 917 F.2d 651, 652 (1st Cir. 1990), the Magistrate Judge

denied Díaz's motion to dismiss Count One. The Magistrate Judge

explained that the elements of the statute Díaz was charged with

violating in that count, 18 U.S.C. § 952, are different from the

elements of the statute Díaz was charged with violating in the

one-count Florida case and therefore his prosecution on Count One

in the Puerto Rico case presented no double jeopardy problem.

With respect to Count Two of the Puerto Rico indictment,

the Magistrate Judge held that the conspiracy for which Díaz was

charged in the Puerto Rico indictment was a separate one from the

conspiracy for which he was charged in the Florida district court.

Applying the five-factor test we laid out in United States v.

Laguna-Estela, 394 F.3d 54, 56 (1st Cir. 2005), the Magistrate

Judge concluded that three of the Laguna-Estela factors -- the

time of the activities, the persons involved, and the evidence

that would be adduced at trial -- favored the government.

First, as to timing, the Magistrate Judge noted that the

conspiracy charged in Puerto Rico "ended in September 2012," and

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therefore "covers a different time period than the conspiracy

alleged in the Florida indictment, which began in October 2012."

Second, as to personnel, the Magistrate Judge emphasized that the

August conspiracy -- the one charged in Puerto Rico -- involved

Suárez and Perpiña, whereas the December conspiracy -- the one

charged in Florida -- involved De León and Concepción. Finally,

as to evidence, the Magistrate Judge noted that there "were two

different drug shipments, involving different time periods and

persons," which "supports a finding that distinct evidence would

have to be adduced in order to establish each of the two

conspiracies." "What is more," the Magistrate Judge held, "because

none of the individuals in the December 2012 conspiracy (apart

from Díaz) were involved in the alleged August 2012 conspiracy,

the government may prove an agreement –– the essential component

of a conspiracy –– between Díaz and the individuals in the August

2012 voyage without resorting to proof of an agreement between

Díaz and the individuals involved in the December 2012 voyage."

The Magistrate Judge, however, held that the remaining

two Laguna-Estela factors -- the places involved and the fact that

the two statutory provisions under which Díaz was charged were the

same -- did weigh in favor of Díaz. The Magistrate Judge noted

that "either the 'Dominican Republic or Puerto Rico' were the

'final destination' for the shipments" charged in both

indictments. (citation omitted). And, the Magistrate Judge also

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noted that Count Two of the Puerto Rico indictment and the one

count of the Florida indictment both "alleged violations of the

same statutory provisions," thus tipping the fifth Laguna-Estela

factor in Díaz's direction. But, after weighing these five

factors, the Magistrate Judge ultimately concluded that the

conspiracies charged in the two indictments were separate ones

insofar as the conduct charged in the two indictments involved

distinct time periods, personnel, and evidence, and recommended

that the District Court deny Díaz's motion to dismiss Count Two of

the Puerto Rico indictment on double jeopardy grounds.

The Magistrate Judge's report and recommendation

informed Díaz that he had fourteen days to file objections. The

report and recommendation also notified Díaz that "[f]ailure to

file timely and specific objections . . . [would constitute] a

waiver of the right to appellate review." Díaz, however, did not

file any objections to the report and recommendation. Accordingly,

on April 26, 2016, the District Court adopted the Magistrate

Judge's report and recommendation that Díaz's motion to dismiss be

denied and directed that the parties proceed with trial

preparation.

Díaz then filed this timely interlocutory appeal. We

agree with the parties that we have jurisdiction to hear the appeal

pursuant to the Supreme Court's decision in Abney v. United States,

431 U.S. 651, 661-62 (1977), which made clear that a "double

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jeopardy challenge to [an] indictment must be reviewable" before

the defendant is to stand trial on that indictment. United States

v. Toribio-Lugo, 376 F.3d 33, 37 (1st Cir. 2004) (noting that,

while ordinarily a "defendant cannot pursue an immediate appeal

from an interlocutory order in a criminal case," defendants may

nevertheless "immediate[ly] appeal[] from denials of a motion to

dismiss" if the appeal is "premised on colorable double jeopardy

grounds").

II.

As this case comes to us, it appears that Díaz waived

his right to bring the challenge he now advances by failing to

file objections to the Magistrate Judge's report and

recommendation. See United States v. Lugo Guerrero, 524 F.3d 5,

14 (1st Cir. 2008) (holding that the defendant "waived his right

to . . . appeal because he failed to object to the recommendation

of the magistrate's report"); see also Thomas v. Arn, 474 U.S.

140, 142 (1985) ("The question presented is whether a court of

appeals may exercise its supervisory powers to establish a rule

that the failure to file objections to the magistrate's report

waives the right to appeal the district court's judgment. We hold

that it may."); Davet v. Maccarone, 973 F.2d 22, 31 (1st Cir. 1992)

("Failure to raise objections to the Report and Recommendation

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waives the party's right to review in the district court and those

claims not preserved by such objection are precluded on appeal.").

Díaz contends that his double jeopardy claim is exempt

from the ordinary application of these waiver rules because his

guilty plea in the Florida case does not now foreclose him from

bringing this double jeopardy challenge. It is by no means clear,

however, that, under United States v. Broce, 488 U.S. 563, 571

(1989), Díaz's failure to object to the Magistrate Judge's report

and recommendation did not thereby waive his right to bring this

challenge. See id. (holding that "when [the defendants] pleaded

guilty to two charges of conspiracy on the explicit premise of two

agreements which started at different times and embraced separate

objectives, they conceded guilt to two separate offenses," and

therefore could not subsequently "challenge the theory of the

indictments and . . . attempt to show the existence of only one

conspiracy"); see also United States v. Stefanidakis, 678 F.3d 99-

100 (1st Cir. 2012). Nevertheless, even assuming that Díaz has

not waived his right to bring this challenge, we conclude, as we

now explain, that this interlocutory appeal fails on the merits.

A.

Díaz purports to challenge both counts of the Puerto

Rico indictment on double jeopardy grounds. But, as Díaz does not

dispute the District Court's conclusion that Count One of the

Puerto Rico indictment did not present a double jeopardy problem

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because it charged an offense that was not charged in the Florida

case, we affirm and proceed to consider his challenge regarding

Count Two of the Puerto Rico indictment.3

The government contends that we review the District

Court's ruling under Laguna-Estela for abuse of discretion. See

Toribio-Lugo, 375 F.3d at 38 ("The baseline standard of review

applicable to a denial of a motion to dismiss on double jeopardy

grounds following the declaration of a mistrial is abuse of

discretion."). Laguna-Estela itself, however, seems to have

applied a clear-error standard of review, 394 F.3d at 57. That

case notwithstanding, we held in United States v. Fornia-Castillo,

408 F.3d 52, 68 (1st Cir. 2005) -- decided several months

afterwards -- that "[t]he availability of double jeopardy

protection is a constitutional question reviewable de novo." Here,

because our conclusion holds irrespective of the standard of

review, rather than choose among the various standards, we apply

the more defendant-friendly standard of de novo review that Díaz

contends is applicable. For even on de novo review, we disagree

with Díaz that the District Court's denial of Díaz's motion to

dismiss must be reversed under Laguna-Estela.

3 Because the District Court adopted the unobjected-to
Magistrate Judge's report and recommendation, our references to
the District Court's reasoning and conclusions encompass the
Magistrate Judge's report and recommendation.

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 Díaz first contends that there is a substantial overlap

between the evidence at issue in the Florida case and the evidence

that would be adduced at trial here, given the "obvious relatedness

of the conduct." For that reason, he argues, the fourth Laguna-

Estela factor -- whether "the same evidence [would] be used to

prove the two conspiracies," 394 F.3d at 57 -- favors him, rather

than the government, as the District Court concluded. But, Díaz

points to no specific facts in the record before the District Court

that suggest that the District Court incorrectly applied or weighed

this fourth Laguna-Estela factor. And while Díaz also argues that

unidentified "principal players" in the two seizures at issue were

the same -- and thus that the second, personnel-based Laguna-

Estela factor also favors him -- that assertion, without more, is

insufficient to meet his burden of "presenting evidence to

establish a prima facie nonfrivolous double jeopardy claim,"

Laguna-Estela, 394 F.3d at 56 (quoting United States v. Booth, 673

F.2d 27, 30-31 (1st Cir. 1982)), even if we assume that Díaz

preserved this argument below.4 Accordingly, Díaz provides no

4 Below, Díaz stated the following: "The facts of the Puerto
Rico case occur right in the middle of the time frame of the
conspiracy of the Southern District case, refer to the same alleged
conduct . . . and occurred in Puerto Rico. The facts coincide in
place, time, geographic area and factual description." He thus
made no reference to any high-level individuals common to both
conspiracies.

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basis on which the District Court's ruling may be reversed under

the framework we established in Laguna-Estela.

B.

Díaz does make a number of other arguments in support of

his contention that the District Court erroneously denied his

motion to dismiss. None have merit.

Díaz argues that, during the sentencing phase of the

Florida proceedings, the government itself relied on evidence from

the August seizure (the one charged in the Puerto Rico indictment)

to demonstrate his responsibility for the December seizure (the

one charged in the Florida case), thus making clear that Díaz

participated in only one "overarching conspiracy." But, assuming

favorably to Díaz that our review is de novo, we disagree.

The Supreme Court has explicitly rejected the argument

"that double jeopardy principles bar a later prosecution or

punishment for criminal activity where that activity has been

considered at sentencing for a separate crime." Witte v. United

States, 515 U.S. 389, 398 (1995). Thus, the fact that the

government presented evidence to the Florida district court

concerning the seizure for which Díaz was charged in this case

does not suffice to show that the crimes charged in the two cases

are the same for double jeopardy purposes.

Díaz also contends that the motion to dismiss must be

granted based on two aspects of the record that he identifies for

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the first time on appeal. Specifically, he contends that: (1) the

Florida and Puerto Rico indictments were coordinated, and

therefore represented the culmination of a "joint investigation"

between law enforcement authorities in Florida and Puerto Rico and

(2) the government opposed Díaz's request that his defense in the

Florida case be handled by a former federal prosecutor in Puerto

Rico because the Puerto Rico case and the Florida case were

"essentially the same." But, Díaz made no reference to these facts

in his motion to dismiss before the Magistrate Judge, and he did

not object before the District Court to the Magistrate Judge's

report and recommendation. Thus, our review is, at best, for plain

error. See United States v. Catalán-Roman, 585 F.3d 453, 472 (1st

Cir. 2009), as amended (Dec. 23, 2009) (holding that a double

jeopardy claim not raised below is subject to plain error review).

Díaz must therefore show that "(1) that an error occurred (2) which

was clear or obvious and which not only (3) affected the

defendant's substantial rights, but also (4) seriously impaired

the fairness, integrity, or public reputation of judicial

proceedings." Stefanidakis, 678 F.3d at 99 (quoting United States

v. Duarte, 246 F.3d 56, 60 (1st Cir. 2001)).

We are, however, hard pressed to see how, taking Díaz's

characterization of the record as true, the fact that the two

prosecutions were similar enough to be handled by the same team of

prosecutors in and of itself shows that the two conspiracies at

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issue here are, in fact, one conspiracy under the Double Jeopardy

Clause. And Díaz offers no basis on which to conclude that the

District Court's contrary ruling, notwithstanding these facts, was

an error, let alone a clear or obvious one. Thus, we reject this

challenge, too.

Finally, Díaz points to the Eleventh Circuit's decision

vacating and remanding his sentence in the Florida case as one

that requires us to dismiss the indictment on double jeopardy

grounds. But the Eleventh Circuit was plainly not, in so ruling,

passing on whether the Puerto Rico and Florida cases involved the

same conspiracy or different ones. As we have already noted, the

Eleventh Circuit merely overruled the Florida district court's

decision to apply a four-level leadership enhancement to Díaz for

the conspiracy charged in that case (whatever its scope), and

instructed the lower court to reconsider its decision not to apply

a two-level downward adjustment for acceptance of responsibility.

Díaz-Rosado, 615 Fed. Appx. at 571 (finding "no merit in [Díaz's]

challenge to his conviction," and "revers[ing] his sentence and

remand[ing] for resentencing"). For this reason, Díaz's final

challenge must also be rejected.

III.

We affirm the judgment of the District Court.

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