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United States v. Reyes-Santiago

United States Court of Appeals, First Circuit

September 23, 2015

JORGE REYES-SANTIAGO, Defendant, Appellee.


Vivianne M. Marrero-Torres, Assistant Federal Public Defender, with whom Hector E. Guzman-Silva, Federal Public Defender, and Hector L. Ramos-Vega, Assistant Federal Public Defender, Supervisor, Appeals Section, were on brief, for appellant.

Luke Cass, Assistant United States Attorney, with whom Rosa Emilia Rodriguez-Velez, United States Attorney, and Nelson Perez-Sosa, Assistant United States Attorney, Chief, Appellate Division, were on brief, for appellee.

Before Torruella, Lipez, and Barron, Circuit Judges.

LIPEZ, Circuit Judge.

Appellant Jorge Reyes-Santiago ("Reyes") was among 110 defendants charged in a two-count indictment with drug and firearms offenses arising from a massive drug ring operating in public housing projects in Bayamon, Puerto Rico. Most of the high-level members of the conspiracy, Reyes among them, pled guilty pursuant to plea agreements. Other than for Reyes, the sentences imposed on Count One, the drug count, ranged from 78 months to 324 months, [1] the latter imposed on the chieftain of the enterprise. Reyes received the stiffest Count One sentence: 360 months. In this appeal, he seeks resentencing on Count One on three grounds: the government's alleged breach of his plea agreement, the sentencing court's alleged inappropriate conduct in demanding witness testimony, and the disparity between his sentence and those of similarly situated co-defendants. Reyes also claims the district court erred in ordering a 24-month consecutive sentence for his violation of supervised release conditions imposed in an earlier case.

We find merit in the disparity argument. Ultimately, [2] in sentencing the lead conspirators, the district court refused to accept stipulated drug amounts only for Reyes, listed as Defendant #9 in the indictment, and for the conspiracy's kingpin, Defendant #1. Although sentencing courts have the discretion to reject recommendations made in plea agreements, and need not uniformly accept or reject such stipulations for co-defendants, they nonetheless must impose sentences along a spectrum that makes sense, given the co-defendants' criminal conduct and other individual circumstances. In this case, after reviewing Presentence Investigation Reports ("PSRs") and sentencing transcripts for the leaders in the conspiracy, we conclude that the rationale offered by the district court for the substantial disparity between Reyes's sentence and the sentences of others above him in the conspiracy's hierarchy is unsupported by the record. We therefore must remand this case to the district court for reconsideration of Reyes's sentence.

Given that resentencing must occur, we need not decide whether the government breached Reyes's plea agreement in the prior sentencing proceedings. However, we discuss certain aspects of the government's performance to provide guidance for the proceedings on remand. Finally, as explained below, resentencing also is necessary for Reyes's violation of his. conditions of supervised release.


Before delving into the substance of this case, we address the government's motion to dismiss the appeal on the ground that it was not timely filed.[3] Under Federal Rule of Appellate Procedure 4(b), with exceptions inapplicable here, a notice of appeal in a' criminal case must be filed within fourteen days of the entry of judgment. In United States v. Gonzalez-Rodriguez, 777 F.3d 37 (1st Cir. 2015), we explained that the filing of a motion seeking reconsideration of a criminal sentence does not extend Rule 4(b)'s filing period. Id. at 41. Reyes properly recognizes that his appeal is untimely under Gonzalez-Rodriguez, as he filed his notice of appeal more than five months after judgment entered.[4] He argues, however, that the government both waived and forfeited its untimeliness challenge. As explained below, we agree that the time limit set by Rule 4(b) may be waived and that the government did so in this case.

A. The Consequence of Untimely Filing

Although we previously have described the time limits in Rule 4(b) as "mandatory and jurisdictional, " United States v. Rapoport, 159 F.3d 1, 3 (1st Cir. 1998) (internal quotation marks omitted); see also Gonzalez-Rodriguez, 777 F.3d at 40 n.4, more recent Supreme Court cases have pointed out the difference between "'a rule governing subject-matter jurisdiction and an inflexible claim-processing rule, '" Eberhart v. United States, 546 U.S. 12, 13 (2005) (per curiam) (quoting Kontrick v. Ryan, 540 U.S. 443, 456 (2004)) . In the latter instance, a failure to adhere to prescribed time limits does not foreclose jurisdiction, but may bar the tardy litigant from securing the relief sought if the opposing party properly objects. See Kontrick, 540 U.S. at 456 (noting that "a claim-processing rule, . . . even if unalterable on a party's application, can nonetheless be forfeited if the party asserting the rule waits too long to raise the point"); see also Eberhart, 546 U.S. at 19.[5]

We have not had occasion to revisit our earlier precedent describing Rule 4(b) as jurisdictional, but every circuit to decide the issue since Kontrick and Eberhart has concluded that Rule 4(b) is a claims-processing rule and, hence, may be waived or forfeited. See United States v. Gavtan-Garza, 652 F.3d 680, 681 (6th Cir. 2011) (per curiam) (citing cases) . As the other circuits have interpreted the Supreme Court's cases, the distinction rests on whether the time-bar at issue originated in a statute. Id. We see merit in that view, which draws support from the Court's comparison in Bowles v. Russell, 551 U.S. 205 (2007), between the "longstanding treatment of statutory time limits for taking an appeal as jurisdictional, " and the conclusion in Kontrick that the limitations period at issue was a claims-processing rule.- Bowles, 551 U.S. at 210-11. In Bowles, the Court observed that critical to the Kontrick holding was "the fact that ' [n] o statute specifies a time limit for filing a complaint objecting to the debtor's discharge.'" (quoting Kontrick, 540 U.S. at 448) (alteration and omission in original)). Id. at 211; see also id. at 211-12 (referring to "the jurisdictional distinction between court-promulgated rules and limits enacted by Congress").

Rule 4(b) does not arise from a statutorily imposed time constraint, [6] and we see no rationale for crossing the line the Supreme Court seemingly has drawn between statute-based time limits and those without legislative origin.[7] Hence, we hold that Rule 4(b)'s time limits are not "mandatory and jurisdictional" in the absence of a timely objection from the government. We thus must consider whether the government waived or forfeited its challenge to appellant's tardiness.

B. Waiver or Forfeiture

The government's motion to dismiss reflected a belief that it may object to a late filing under Rule 4(b) at any time, and, once it does, the court is obliged to enforce the rule. It therefore asserted that its motion -- filed three months after this case was submitted for decision following oral argument -- required us to dismiss Reyes's appeal. In so arguing, the government relied on the statement in Gonzalez-Rodriguez that the time limits in Rule 4(b), "even if not jurisdictional, are mandatory when raised by the government." 777 F.3d at 40 n.4. In Gonzalez-Rodriguez, however, the government had contended in its original response brief that the court had no jurisdiction to consider the defendant's sentencing appeal. Here, by contrast, the government suggested in a footnote in its original brief that Reyes's appeal was timely because the fourteen-day clock for filing a notice of appeal did not begin to run until after the district court denied Reyes's motion for reconsideration. In pertinent part, the footnote states:

"[T]he Supreme Court has held that the timely filing of such a motion [for reconsideration] in a criminal action tolls the time for filing a notice of appeal and the time begins to run anew following disposition of the motion." United States v. Vicaria, 963 F.2d 1412, 1413-14 (11th' Cir. 1992 [)] (citing United States v. Dieter, 429 U.S. 6, 8-9 (1976[)]; see also United States v. Ortiz, No. 12-2190, 2014 WL 278510, at *5, n. 2 (1st Cir. Jan. 27, 2014) ("motions for reconsideration in criminal cases are not specifically authorized either by statute or by rule"); United States v. Healv, 376 U.S. 75, 84 (1964[)]. "Amotion for reconsideration in a criminal case must be filed within the period of time allotted for filing a notice of appeal in order to extend the time for filing the notice of appeal." See United States v. Russo, 760 F.2d 1229, 1230 (11th Cir. 1985) .

Gov't Br. at 3 n.2.

The government attempted to characterize the footnote as something other than a concession of timely filing and appellate jurisdiction. Although the passage may not be an explicit concession, it is nearly so. The government sought to justify its acquiescence with the fact that Gonzalez-Rodriguez was decided after its brief was filed, insinuating that the prosecutors did not have reason before then to raise a timeliness objection. But the brief in Gonzalez-Rodriguez raising the jurisdictional argument was filed by the same United States Attorney's Office responsible for this case more than two months before it submitted the response brief that contains the footnote. The government did not explain why it could not have made the same time-bar argument here. Moreover, the panel's opinion in Gonzalez-Rodriguez simply pulled together pre-existing authorities. See, e.g.. United States v. Dotz, 455 F.3d 644, 648 (6th Cir. 2006) ("In the sentencing context, there is simply no such thing as a 'motion to reconsider' an otherwise final sentence . . . ." (quoted in United States v. Ortiz, 741 F.3d 288, 292 n.2 (1st Cir. 2014)). Plainly, as its argument in Gonzalez-Rodriguez demonstrates, the government had ample basis to challenge the jurisdiction for this appeal in its original response brief. Thus, we have here a situation that is fairly characterized as a waiver.

Moreover, even absent the jurisdictional footnote, the government's request for dismissal would have confronted the maxim that any issue not raised in a party's opening brief is forfeited. See, e.g., United States v. Turn, 707 F.3d 68, 72 n.2 (1st Cir. 2013) . The government cited no case in which a court has found adequate the government's request for dismissal of an appeal, based on Rule 4(b)., when the objection was raised for the first time after the government had filed its response brief. The forfeiture discussion in other cases has focused on whether the government needed to raise the issue before filing its brief. See, e.g., Sadler, 480 F.3d at 941 (agreeing with other circuits that "raising the untimeliness argument in briefing, as opposed to in a motion to dismiss, was sufficient to invoke Rule 4's protections"); see also United States v. Garduno, 506 F.3d 1287, 1292 n.7 (10th Cir. 2007) (advising the government to consider filing a motion for dismissal under Fed. R. App. P. 27 and the applicable Tenth Circuit rule "when the government recognizes a violation of Rule 4(b)(1)(A), " but stating that failure to do so "does not constitute a forfeiture where, as here, the appellee seeks dismissal for failure to timely appeal in its response brief"); cf. Huerta v. Gonzales, 443 F.3d 753, 757 (10th Cir. 2006) (finding that the government had forfeited objection to a claim-processing rule because it responded on the merits to petitioner's late-filed appeal).[8]

Applying ordinary forfeiture principles in this context is consistent with the Supreme Court's assertion in Eberhart that "[t]hese claim-processing rules . . . assure relief to a party properly raising them." 546 U.S. at 19 (emphasis added). Further, in Kontrick, the Court endorsed the notion that "[t]ime bars . . . generally must be raised in an answer or responsive pleading." 540 U.S. at 458. Although the Court's reference was to trial court proceedings, the obligation to "timely assert[] the untimeliness" of a litigation adversary's conduct is equally applicable on appeal. Id. Hence, even if the government had not waived the timeliness issue, we would hold that the claim was forfeited because it was not raised in its opening brief.


In assessing Reyes's challenge to his sentence in the conspiracy case, we draw the facts from his and his co-defendants' change-of-plea and sentencing hearings, PSRs, and plea agreements. See United States v. Rivera-Gonzalez, 776 F.3d 45, 47 (1st Cir. 2015).[9]

A. Sentencing Overview

Count One of the indictment against Reyes and his numerous co-defendants alleged possession with the intent to distribute substantial quantities of various drugs -- including heroin, crack cocaine, and cocaine -- in a conspiracy that operated at four public housing projects in Bayamon at least from 2005 to 2010. See 21 U.S.C. §§' 841(a), 846, 860. Count Two charged the defendants with aiding and abetting their co-conspirators in using and carrying firearms in connection with the drug trafficking enterprise identified in Count One, in violation of 18 U.S.C. §§ 924(c)(1)(A) and 2.

The indictment divided the defendants into multiple groups: the Leaders (defendants ##1-5), Managers/Drug Owners (defendants ##6-14), Supplier (defendant #15), Enforcers (defendants ##16-17), Runners (defendants ##18-34), Sellers (defendants ##35-84), Lookouts (defendants ##85-106), and Facilitators (defendants ##107-110). Reyes, #9, was in the second tier and designated a Manager/Drug Owner.[10] The PSRs for the top defendants stated that, during the enterprise's five-year span, it was responsible for distributing approximately the following amounts of drugs: 210 kilograms of heroin, 485 kilograms of crack cocaine, 505 kilograms of cocaine, 2, 000 kilograms of marijuana, and undetermined amounts of Percocet and Xanax pills.

Most of the high-level defendants pled guilty pursuant to non-binding plea agreements and were sentenced by the district court judge here. The plea agreements contained recommended sentences or sentencing ranges based in part on stipulated amounts of cocaine, [11] with some recommendations contingent on the defendant's not-yet-determined Criminal History Category ("CHC"). Most of the agreements also included stipulations on whether a role-in-the-offense enhancement should be added to the Base Offense Level ("BOL"), and the extent of any such increase. The stipulated drug amounts, the sentences or sentencing ranges recommended by the government, and the sentences actually imposed for nine of the top ten defendants, including Reyes, are as follows:[12]


Stipulated Drug Amt.

Recommended Term

Count One Sentence

#1 Jose Colon de Jesus
5-15 kilos
180 months
324 months

#2 Angel Colon de Jesus

3.5-5 kilos

168 months

135 months

#3 Jimenez-Echevarria

2-3.5 kilos

108 months

108 months

#4 Sevilla-Oyola
2-3.5 kilos
240 months[13]

#6 Adalberto Rivera Bermudez

3.5-5 kilos

135 months

151 months

#7 Rafael Nazario-Pedroza

2-3.5 kilos

78 months

78 months

#8 Sadid Medina-Rivera

5-15 kilos[14]

151 months

121 months

#9 Appellant

2-3.5 kilos

100 months

360 months

#10 Luis Ramos-Oyola
2-3.5 kilos
78 months
78 months

Thus, as the chart reveals, Reyes's 360-month sentence is the longest of any of the defendants, including both the conspiracy's leader and a career offender, and his term exceeds most of the other sentences by wide margins. Also pertinent to this appeal are two facts applicable only to Reyes, Sevilla-Oyola and Jose Colon de Jesus -- i.e., the three co-defendants with the longest sentences. First, the district court heard witness testimony at sentencing only for those three, relying in the remaining cases on the PSRs, the plea agreements, and the parties' arguments. Second, those three defendants were implicated in notorious killings: the so-called "Pitufo Murder" and the "Pajaros Massacre." Reyes and Colon de Jesus were acquitted in state court on charges stemming from the latter, in which a drug dealer, his two-year-old daughter, and another individual were killed in a barrage of shots in Toa Alta, Puerto Rico, in 2009. Sevilla-Oyola was identified by a cooperating witness as the shooter in the Pitufo incident, in which another co-conspirator under federal supervision (Jose Manuel Torres-Morales, known as "Pitufo") was murdered in front of the federal courthouse in Hato Rey, Puerto Rico, in 2007. See United States v. Sevilla-Ovola, 770 F.3d 1, 5 (1st Cir. 2014).

B. Reyes's Sentencing

1. Plea Agreement and PSR

As reflected in the chart above, Reyes's plea agreement stipulated that he was accountable for at least 2 but less than 3.5 kilograms of cocaine, which produced a BOL of 28. With a two-level enhancement because the drug trafficking occurred in a protected location, see U.S.S.G. § 2D1.2(a)(1), and a three-level reduction for acceptance of responsibility, see U.S.S.G. § 3E1.1, his proposed total offense level was 27. The government agreed to recommend a sentence of 87 months if Reyes's CHC was III or below, and if the CHC was higher, the government would recommend a sentence at the low end of the applicable guidelines range. No role enhancement was proposed. Because Reyes's CHC turned out to be IV, the Guidelines range consistent with the plea agreement was 100 to 125 months.

Reyes's PSR, however, calculated a substantially longer Guidelines sentence. Although the PSRs for most of the defendants listed in the chart above used the cocaine amounts stipulated in the plea agreements for their BOL calculations, the PSRs for Reyes and the conspiracy's head, Jose Colon de Jesus, used the higher quantities alleged by law enforcement authorities. Based on roughly 241, 000 kilograms of marijuana, [15] Reyes's BOL was 38. The PSR added both the two-level enhancement for protected location proposed in the plea agreement and three levels for Reyes's role in the offense. With the three-level reduction for acceptance of responsibility, the total offense level was 40. The PSR calculated Reyes's CHC to be IV, producing a Guidelines range of 360 months to life. The PSR also included information about the Pajaros Massacre as criminal conduct that might warrant a departure or variance from the Guidelines range.

In a February 2012 order applicable to both Reyes and Colon de Jesus, prior to their sentencing hearings, the district court directed the government to produce evidence on the amount of drugs trafficked during the conspiracy and to secure testimony from three sources: (1) a "cooperating witness" to the Pitufo Murder, (2) "the principal witness" to the Pajaros Massacre, and (3) witnesses familiar with "the facts behind the extensive criminal activity that ended up dismissed in state court throughout the years." The court advised the two defendants that it had obtained the full transcript of the Pajaros trial and that it was available for examination by the parties. The court also made available to those two defendants, along with Sevilla-Oyola, police and FBI reports about the Pitufo Murder that it had obtained from the United States Marshal. Subsequently, however, after an informal status conference with counsel for Colon de Jesus, the district court notified both defendants that it would not take the Pitufo Murder or Pajaros Massacre into account for their sentencings. The court stated that it would hear testimony only on "drug amount, dismissed criminal prosecutions and nature of the drug trafficking charge in referen[ce] to firearms and violence."

2. The Hearing and Aftermath

At the outset of Reyes's sentencing hearing, held in May 2012, the district court noted that it was not bound by the plea agreement and .observed that "the amount of drugs in this case is so huge, so huge that it makes it up to a certain point unacceptable to adopt the stipulation." In response, defense counsel pointed out that the same judge had accepted the drug stipulations during prior sentencings of Defendants #2 (Angel Colon de Jesus), #3 (Jimenez-Echevarria), #6 (Rivera Bermudez), and #7 (Nazario-Pedroza). The court responded by noting that the conspiracy's leader had "relied a lot" on Reyes and that "he was also like a Lieutenant to number one." The court further explained that he was "not happy . . . with the stipulation in this case regarding narcotics, because there is an issue as to whether he was something larger, bigger in the organization than what he pled to, " and noted its understanding that Reyes "was the owner of th[e] Boston Red Sox marijuana [marijuana sold for $6/bag], and he was like an assistant to number one." The court directed the government to present its witness to clarify "the issue of role and the issue of drugs."

Before the witness took the stand, however, the parties and the court discussed defense counsel's contention that the government's examination of the witness would be a breach of the plea agreement. After the objection was addressed, [16] and before the witness testified, counsel again raised the differential treatment among defendants, prompting the following exchange:

COUNSEL: But then my question, Your Honor, that we have with these people that are numbers higher in the ranking of this Indictment --
COURT: It doesn't matter. The cases are different.
COUNSEL: The cases are the same, Your Honor.
COURT: Presentence Reports are different. Criminal records are different.
COUNSEL: Exactly, but then I go back, why is it, why is it that the Presentence Report for my client is different than probably the other ones? I wonder if the other ones received the same calculations as to the whole amount of the drugs, and not -- than Mr. Reyes did? And I can only say, I can only understand or figure out that it might be because he was acquitted of the P[a]jaros massacre.
We can always say that we are not considering this, we are not considering that; but it's still there, because no one wants to be --
COURT: Absolutely, it's still there. Yes.
COUNSEL: It's still there. So that's why I wanted to place the Court in a position to understand that my client was the only one that presented an alibi defense [in the Pajaros case], and that alibi defense was not shady. It was good.
And then because that probably we --the Court and the Probation Office and the Government might have a different eye to my client, instead, and probably he would get there like the other ones that were already sentenced.

Defense counsel sought to provide the court with evidence substantiating Reyes's Pajaros alibi, but the court said it was "not going to go anymore into the P[a]jaros massacre, " noting that the crime "is a dead case for me." The court then directed the government to call its witness, Carlos Burgos Rodriguez ("Burgos"), to elicit testimony on Reyes's "involvement with this particular brand of marijuana that we've been talking about" and "his involvement with number one in the context of role."

Burgos, a cooperating co-defendant who was a runner at the Virgilio Davila Public Housing Project, [17] testified that Reyes's "position there was to find the workers, to assign the shifts, to organize the runners, and to look out for the stash that was kept there, the drugs." He reported that Reyes at one point received a commission from the sale of four drugs -- including "the Boston" --that "belonged" to Colon de Jesus, but that the profits from that brand of marijuana (i.e., the Boston Red Sox variety) were divided among five individuals after the death of Pitufo: Reyes, Sevilla-Oyola, Jimenez-Echevarria, Rodriguez-Rodriguez, and an individual whom Burgos identified as "Menovito" and added, "may he rest in peace."

Based on this testimony, the district court found "by more than a preponderance of the evidence" that Reyes was a supervisor, and it concluded that the three-level role enhancement included in the PSR calculation was appropriate. The court also stated that "a person with this degree of supervision and involvement in the conspiracy knew or should have known the extent of the drug amounts that were handled by this conspiracy, and it wasn't what is stipulated." In response to these findings, defense counsel returned to the issue of disparity:

COUNSEL: Then, Your Honor, I would just renew my objection as to the other people, the other defendants that were sentenced prior to Mr. Reyes Santiago, who have administrator or supervision roles, and they were not attributed this amount of drugs as -- and they were probably foreseeable to them, too. And that treatment --
COURT: I don't remember that being an issue in those cases. I ...

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