United States Court of Appeals 

For the First Circuit 

No. 14-1693 

UNITED STATES OF AMERICA, 

Appellee, 

v. 

ANGEL ORTIZ-VEGA, 

Defendant, Appellant. 

APPEAL FROM THE UNITED STATES DISTRICT COURT 

FOR THE DISTRICT OF PUERTO RICO 

[Hon. Daniel R. Domínguez, U.S. District Judge] 

Before 

Torruella, Thompson, and Kayatta, 

Circuit Judges. 

 Rafael F. Castro Lang for appellant. 

 Nelson Pérez-Sosa, 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 appellee. 

June 21, 2017 
- 2 - 

THOMPSON, Circuit Judge. Appellant Angel Ortiz-Vega 

("Ortiz") was charged with several counts related to a drug 

distribution conspiracy in Puerto Rico. Ortiz was originally 

represented by court-appointed counsel, Francisco M. Dolz-Sanchez 

("Dolz"), but after seven months retained private counsel, Luis R. 

Rivera-Rodriguez ("Rivera"), because, according to Ortiz, Dolz 

failed to provide him with effective assistance of counsel 

throughout plea negotiations. Ortiz raised his ineffective 

assistance claim at several points prior to sentencing, claiming 

that Dolz's lack of adequate communication cost him a better plea 

deal. The district court declined to rule on Ortiz's ineffective 

assistance claim prior to sentencing, finding the motion to be 

"premature." Ortiz eventually pled guilty to a higher plea offer 

negotiated by his new counsel and was sentenced in accordance with 

that agreement. 

On appeal, Ortiz argues, inter alia, that the district 

court erred by refusing to rule on the merits of his ineffective 

assistance claim prior to sentencing. For the reasons discussed 

below, we agree with Ortiz and remand the case to the district 

court for further proceedings. 

Background 

 In the summer of 2011, Ortiz was charged in a nine-count 

superseding indictment along with over a hundred other codefendants allegedly involved in a large-scale drug conspiracy. 
- 3 - 

For his role, Ortiz was charged with conspiracy to possess with 

intent to distribute various controlled substances including 

heroin, cocaine, marijuana, Percocet, and Xanax, as well as the 

actual possession of those substances with intent to distribute 

them, within a thousand feet of a public school in violation of 

21 U.S.C. §§ 841, 846, and 860 (Counts I-IV). Ortiz was also 

charged with aiding and abetting others in the use or possession 

of firearms during the drug offenses in violation of 18 U.S.C. 

§ 924(c) and 2 (Count V). 

On August 6, 2012, Ortiz ultimately entered into a nonbinding plea agreement with the government, pursuant to Federal 

Rule of Criminal Procedure 11(c)(1)(B), in which he agreed to plead 

guilty to the conspiracy and firearms charges (Counts I and V) 

with an applicable United States Sentencing Guidelines 

("Guidelines") range of 168-180 months on both counts. See United 

States v. Torres-Oliveras, 583 F.3d 37, 41 (1st Cir. 2009) 

(discussing the difference between non-binding Type B and binding 

Type C plea agreements). The journey to reach this point of 

agreement had proven long and contentious, with Ortiz switching 

counsel and his previous (court-appointed) counsel, his current 

(privately-retained) counsel, and the government each making 

conflicting assertions as to the facts surrounding Ortiz's plea 

negotiations. We necessarily discuss the facts surrounding 

Ortiz's plea negotiations, since they form the basis of his present 
- 4 - 

appeal and assertion that the district court erred in failing to 

rule on his ineffective assistance claim prior to sentencing. 

 1. Plea Negotiations 

 Ortiz was arrested on the drugs and firearm charges 

described above in late June 2011. At that time, Dolz was 

appointed as his attorney. Dolz asserts that he first met with 

Ortiz in July 2011 to discuss the charges lodged against Ortiz and 

to conduct a full client interview. On January 24, 2012, six 

months after his arrest, Ortiz filed a pro se "Motion for Lawyer 

Dismissal" in which he requested that Dolz be "released from his 

position on [sic] [Ortiz's] case" because, according to Ortiz, 

Dolz had "acted in a [sic] unreasonable way" and had not 

communicated with him since he had been imprisoned. The court did 

not respond to Ortiz's pro se motion until six months after it was 

filed (after Ortiz had replaced Dolz with a privately-retained 

attorney), and the court ultimately dismissed Ortiz's pro se motion 

as moot given his retention of new counsel. The parties dispute 

how often Dolz communicated with Ortiz and the substance of their 

communications during plea negotiations. 

According to Dolz, after Ortiz filed his pro se motion, 

Dolz reached out to the government via email to discuss a possible 

plea offer.1 Dolz asserts that he then visited Ortiz on March 6, 

 1 Dolz also states that there was an initial "verbal" plea 

offer that no one took seriously. Dolz claims that the government 
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2012 -- some eight months after first interviewing Ortiz -- to 

further discuss Ortiz's case. Dolz claims that at this meeting 

Ortiz stated that he would only accept a plea offer of eighty-four 

months (or seven years) for both counts. 

On March 19, 2012, the government offered Ortiz a plea 

deal well above seven years, with a Guidelines range of 130-147 

months (or between a little over ten and a little over twelve 

years) on both counts. Dolz claims that he visited Ortiz again on 

April 7, 2012 to communicate the 130-147 month plea offer. 

According to Dolz, he advised Ortiz to take the offer, but Ortiz 

rejected it and reiterated that he would only accept a plea deal 

of seven years on both counts, or that he would go to trial. Dolz 

claims that as soon as he exited the prison after meeting with 

Ortiz, Ortiz's wife called and informed him that Ortiz no longer 

wanted to present a counteroffer of seven years to the government 

as they had just discussed, but instead wanted to present a 

counteroffer of sixty months on the conspiracy charge (Count I) 

and wanted the firearms charge (Count V) to be dismissed 

altogether. 

 

had initially offered Otiz a verbal plea deal for 240 months 

sometime in August or September of 2011. Dolz claimed that 

although the government had tendered this verbal offer, neither of 

them took the offer seriously. Dolz states that he informed Ortiz 

of this verbal offer, but the record does not specify when Dolz 

communicated this offer or Ortiz's response to it. 
- 6 - 

Accordingly, on April 12, 2012, Dolz emailed the 

government Ortiz's counteroffer of sixty months. The government 

responded to Dolz's email with a one-liner: "Rejected. See you in 

trial then?" The record is ambiguous as to whether Dolz ever 

responded to this rejection of Ortiz's counteroffer, but it does 

indicate that Dolz may not have communicated with Ortiz again 

regarding plea negotiations until after Ortiz had retained new 

counsel three months later in July 2012. 

Dolz asserts that at some point after Rivera had been 

retained (on July 24, 2012), but presumably prior to Dolz's last 

meeting with Ortiz on the following day (July 25, 2012), he 

communicated with the government via email to see if the 130-147 

month offer was still on the table. Dolz claims that the 

government informed him that the original offer had expired and 

that the new offer was 180 months, which the government had also 

communicated to Rivera. Dolz also indicated that the government 

was mistaken in its statement that the original offer had expired 

and claimed that he believed that the original offer of 130-147 

months had not expired and would not expire until July 31, 2012 -

- the date set by the court for any change of plea. 

On July 25, 2012, the day after Rivera filed his 

appearance in the case, Dolz claims that he visited and informed 

Ortiz that "there was a plea offer outstanding and that July 31, 

2012 was the deadline for the [change of plea] motion." It is 
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unclear from the record whether the "outstanding plea offer" 

referenced by Dolz was the new 180 month offer or the previous 

130-147 month offer which Dolz apparently believed had an 

expiration date of July 31, 2012.2 Dolz also asserts that at this 

final July meeting, he informed Ortiz that his previous 

counteroffer of sixty months had been rejected and that there was 

nothing else Dolz could do since Ortiz had retained Rivera to 

handle his case. Despite Ortiz retaining new counsel, Dolz 

contends that the government continued to communicate with him 

concerning Ortiz's case and that on July 31, 2012 the government 

sent him a new plea offer of 168-180 months that was slated to 

expire on August 1, 2012. 

The government mostly agrees with Dolz's account of plea 

negotiations, but also states that after rejecting Ortiz's 

counteroffer of sixty months, it understood that the original 130-

147 month offer had been rescinded. 

 2 It is unclear at what point Dolz was made aware of the 180 

month offer and if he communicated that offer to Ortiz. On the 

one hand, Dolz claims that the government informed him that the 

130-147 month plea offer had expired and that the new plea offer 

was 180 months prior to his meeting with Ortiz on July 25, 2012. 

On the other hand, Dolz claims that he was unaware of the new 168-

180 month offer until July 31, 2012 when the government emailed 

him a new plea agreement. Dolz also indicated that he believed 

that it was Rivera who permitted the original 130-147 month offer 

to expire because Dolz believed that the original offer did not 

expire until July 31, 2012 -- after Rivera had been retained. It 

is therefore also unclear what "outstanding offer" Dolz 

communicated to Ortiz on his visit on July 25, 2012 (180 months or 

130-147 months). 
- 8 - 

As expected Ortiz has a very different view of what 

occurred during plea negotiations. According to Ortiz, Dolz only 

visited him twice: once on April 7, 2012 to communicate the 

original 130-147 month plea offer and again after Ortiz had 

retained Rivera as his new counsel.3 Ortiz claims that Dolz failed 

to keep him updated concerning plea negotiations and failed to 

communicate with him after the government rejected his 

counteroffer. In response to Ortiz's assertions, at a hearing 

before the district court, Dolz said that he "saw [Ortiz] as [he] 

need[ed] to see him" and that Ortiz was given the information 

needed regarding his case despite his assertion that Dolz only 

visited him twice. At another hearing, Ortiz countered that he 

never communicated to Dolz that he would rather go to trial, and 

that he always wanted to plead guilty, but that he was looking for 

the best deal. Of course, Dolz denied these contentions. 

2. Plea Agreement 

Regardless of the back and forth alleged by Ortiz and 

Dolz concerning plea negotiations, Ortiz did finally enter into a 

plea agreement with the government that was negotiated by his new 

counsel Rivera. According to Rivera, by the time he got involved 

 3 Ortiz cites the jail visitation log record to support his 

claim that Dolz only visited him twice. According to those 

records, Dolz visited Ortiz on April 7, 2012 and again after Rivera 

had been retained. As discussed above, Dolz argues that he did 

not always sign the visitation log when he visited Ortiz and that 

there were more than two visits that had not been recorded. 
- 9 - 

with the case, the government refused to offer Ortiz the original 

plea offer of 130-147 months, claiming that its initial offer had 

expired. Ortiz alleges that he was faced with the choice of a 

higher plea deal or trial -- stuck between Scylla and Charybdis, 

he ultimately chose to take the higher plea deal. 

Under the terms of the plea agreement, Ortiz's total 

offense level as to Count I was calculated with a base offense 

level of thirty (for possession of at least 3.5 but less than five 

kilograms of cocaine pursuant to U.S. Sentencing Guidelines Manual 

("USSG") § 2D1.1(c)(5) (U.S. Sentencing Comm'n 2012); plus two 

levels for his role as a manager or supervisor pursuant to USSG 

§ 3B1.1(c); plus two levels for the possession of drugs near a 

public school pursuant to USSG § 2D1.2(a)(1); minus three levels 

for acceptance of responsibility pursuant to USSG § 3E1.1(a)-(b). 

With a resulting total offense level of thirty-one on Count I, the 

applicable Guidelines range was 108-135 months, assuming a 

criminal history category of I.4 

The parties agreed that a consecutive term of sixty 

months' imprisonment was applicable to Count V and ultimately 

agreed to a total Guidelines range of 168-180 months on both 

counts,5 with the government reserving the right to request a 

 4 The parties did not stipulate to the applicable criminal 

history category. 

5 We note that in calculating the total recommended Guidelines 

range the parties agreed to a range of 168-180 months on both 
- 10 - 

sentence at the high end of the Guidelines range and Ortiz 

reserving the right to request a sentence at the low end of the 

Guidelines range.6 The government agreed to dismiss all remaining 

counts against Ortiz and the plea agreement also contained a 

waiver-of-appeals clause that barred Ortiz from appealing his 

sentence if sentenced in accordance with the terms of the 

agreement. Ortiz's change of plea hearing was held on August 6, 

2012 (the same day that he signed the plea agreement).7 

 

counts; however, when we tally the independently calculated 

Guidelines ranges provided for each individual count in the plea 

agreement (108-135 months on Count I and sixty months on Count V), 

we would expect the total agreed-upon sentence to be between 168-

195 months -- fifteen months greater than the total actually agreed 

to by the parties. 

6 The plea agreement has several errors that were not 

corrected before signing. For instance, it is clear that in the 

original draft of the plea agreement, the government sought to 

hold Ortiz responsible for at least two kilograms, but not more 

than 3.5 kilograms, of cocaine. However, the parties edited the 

plea agreement by hand to hold Ortiz responsible for at least 3.5 

kilograms, but less than five kilograms of cocaine. The correlated 

references to the Sentencing Guidelines were not corrected (i.e., 

instead of a reference to USSG § 2D1.1(c)(6), the proper section 

utilized to arrive at a base offense level of 30 was USSG § 

2D1.1(c)(5)). Although we note the discrepancies, these 

typographical errors are of no consequence to our analysis here. 

7 As noted above, on appeal, Ortiz does not challenge the plea 

agreement entered nor does he seek to withdraw his guilty plea. 

He instead argues that the district court erred in failing to 

address the merits of his ineffective assistance claim prior to 

sentencing. 
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3. Sentencing 

After pleading guilty, and before sentencing, Ortiz 

filed a pro se letter with the district court on November 8, 2012, 

again complaining about Dolz's representation during plea 

negotiations. In the letter, Ortiz did not request any specific 

relief beyond a "just sentence," but he again argued that Dolz 

visited him only once during plea negotiations and that Dolz never 

communicated with him further after that one meeting. Ortiz 

claimed that Dolz "neither advised [him] or represented [him] well" 

and that "[Dolz] completely abandoned [him]." In April 2013, 

Rivera filed a sentencing memorandum on Ortiz's behalf, 

highlighting Ortiz's complaints from the November letter about 

Dolz's representation and asserting Ortiz's ineffective assistance 

claim. In that memorandum, Rivera argued that Ortiz should be 

sentenced in accordance with the original plea offer of 130-147 

months. 

In a hearing on April 8, 2013 (at which Dolz was not 

present), Rivera discussed Ortiz's ineffective assistance claim 

and indicated to the court that he wanted to renegotiate the plea 

deal. The government responded that it would not renegotiate the 

plea deal. Rivera also argued that at the time Ortiz's family 

contacted him to represent Ortiz, Dolz "had not gone over to 

discuss with [Ortiz] either the discovery nor [sic] a possible 

plea." The court scheduled another hearing (in fact, numerous 
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hearings followed over the next 13 months to discuss Ortiz's 

ineffective assistance claim) and instructed Dolz to be present. 

The court noted that "the best thing to do is to allow Mr. Dolz to 

answer [Ortiz's ineffective assistance claim], and then the Court 

will make a determination." Accordingly, Dolz eventually answered 

Ortiz's claim, filing a written response to Ortiz's sentencing 

memorandum prior to sentencing. Rivera sought access to Dolz's 

case files concerning Ortiz's plea negotiations, which both Dolz 

and the government were ordered to (and presumably did eventually) 

produce. 

On April 21, 2014 a hearing took place, with Dolz 

present, and Rivera sought to call him to the stand. Dolz 

responded that he was "not in a position to testify" and that he 

had a conflict.8 After listening to the numerous contentions made 

by the parties concerning how often Dolz visited Ortiz, whether or 

not Ortiz was seeking to withdraw his guilty plea, and other issues 

surrounding Ortiz's claim, the district court rescheduled the 

 8 Dolz specifically stated: 

I am not in a position to testify, to appear. 

I could argue, I could present evidence, I 

could find documents, but I am in no condition 

whatsoever. This is taking time. It is going 

to take more time. I am still yet under 

certain jurisdictions. This is not that. 

. . . 

I am impeded. I have a conflict, if I take 

the stand. 
- 13 - 

matter again, this time explicitly "put[ting] the case [down] for 

a two-day [evidentiary] hearing." Dolz was ordered to be present 

with counsel. 

On May 21, 2014, before the evidentiary hearing 

scheduled for that date got underway, Rivera filed a supplemental 

memorandum further detailing Ortiz's ineffective assistance claim. 

When it was his turn to address the court, Rivera repeatedly stated 

that Ortiz was not seeking to withdraw his guilty plea, but that 

he wanted the judge to consider Ortiz's ineffective assistance 

claim in order to sentence him according to the terms of the 

original plea offer of 130-147 months. The district court, after 

listening to arguments from both sides, ultimately ruled that "to 

the extent that this may be a camouflaged motion to withdraw a 

plea, the Court denies the request because the timing is not 

proper. [Ortiz] is not alleging that he's innocent, and to that 

effect, if it is a motion to withdraw the plea, it is denied." 

The district court held further that "to the extent that [Ortiz's 

memorandum on ineffective assistance] is a 2255, it is premature." 

At sentencing, held that very same day, Rivera also 

argued that the district court should sentence Ortiz at the lower 

end of the applicable Guidelines range because similarly-situated 

co-defendants had received sentences of nine, ten, or eleven years. 

Ultimately, the district court declined to rule on the merits of 

Ortiz's ineffective assistance claim, rejected his sentencing 
- 14 - 

disparity arguments, and sentenced him in accordance with the plea 

agreement to a total of 174 months or 14.5 years (near the top of 

the applicable Guidelines range). 

After filing the instant appeal, Ortiz filed a motion to 

reduce his sentence before the district court pursuant to 18 U.S.C. 

§ 3582(c)(2), which was granted on December 30, 2015, during the 

pendency of this appeal. 

Analysis 

 On appeal, Ortiz primarily argues that the district 

court erred in: (1) failing to address the merits of his 

ineffective assistance claim prior to sentencing; and (2) failing 

to adequately address his sentencing disparity arguments.9 Because 

we ultimately remand to the district court to conduct whatever 

proceedings are necessary to rule on Ortiz's ineffective 

assistance claim (for reasons discussed in more detail below), we 

decline to delve into the merits of his sentencing disparity 

argument at this time. 

 9 Ortiz also argues that the district court erred in ruling 

on his motion for a reduction of sentence prematurely. Both 

parties agree that the district court lacked jurisdiction to rule 

on the motion while this appeal was pending. See United States v. 

Cardoza, 790 F.3d 247, 248 (1st Cir. 2015) ("[A] district court 

does not have jurisdiction to enter a sentence modification order 

under § 3582(c)(2) while an appeal of that sentence is pending"). 

We, therefore, vacate the district court's ruling on the sentence 

reduction and remand this issue "so that the district court, once 

its jurisdiction has reattached, may consider reducing [Ortiz's] 

sentence." United States v. Rodríguez-Milián, 820 F.3d 26, 36 

(1st Cir.), cert. denied, 137 S. Ct. 138 (2016). 
- 15 - 

 1. Waiver 

As a threshold matter, we must determine whether Ortiz's 

claims are barred by the waiver-of-appeals clause found in his 

plea agreement. Ortiz concedes that he entered into his plea 

agreement knowingly and voluntarily. However, he argues that the 

waiver-of-appeals clause should not be enforced because to do so 

would work a miscarriage of justice in that his plea negotiations 

were tainted by ineffective assistance of counsel. The government 

says the waiver-of-appeals clause is enforceable because Ortiz's 

ineffective assistance claim results in no miscarriage of justice 

since he "may present his claim through a 2255 motion" and is 

therefore not prejudiced by the court's finding that his claim was 

premature.10 

This court has recognized that "if denying a right of 

appeal would work a miscarriage of justice, the appellate court, 

in its sound discretion, may refuse to honor the waiver." United 

States v. Teeter, 257 F.3d 14, 25 (1st Cir. 2001). 

In determining whether a miscarriage of justice would 

result, we consider, among other factors, "the clarity of the 

alleged error, its character and gravity, its impact on the 

defendant, any possible prejudice to the government, and the extent 

 10 The government also argues that Ortiz's sentencing 

disparity claim is barred by the waiver-of-appeals clause because 

he knowingly and voluntarily entered into a valid plea agreement. 
- 16 - 

to which the defendant acquiesced in the result." United States 

v. Pratt, 533 F.3d 34, 37 (1st Cir. 2008) (quoting United States 

v. Cardona-Díaz, 524 F.3d 20, 23 (1st Cir. 2008)). We have noted 

that the miscarriage-of-justice exception has been applied 

"sparingly and without undue generosity" and is therefore reserved 

for egregious circumstances. United States v. De-La-Cruz Castro, 

299 F.3d 5, 13 (1st Cir. 2002) (quoting Teeter, 257 F.3d at 26). 

Nevertheless, in Teeter, we listed, inter alia, certain categories 

of cases which may fall within the miscarriage-of-justice 

exception, specifically recognizing "situations in which 

appellants claim that their sentences were based on 

constitutionally impermissible factors (say, race or 

ethnicity) . . . or that the plea proceedings were tainted by 

ineffective assistance of counsel." Teeter, 257 F.3d at 25 n.9 

(internal citations omitted). 

Applying those principles, we first note the unique 

posture of Ortiz's argument: Ortiz is not alleging that the 

attorney who negotiated the plea deal that Ortiz actually entered 

into (Rivera) provided ineffective assistance, but that his prior 

attorney (Dolz) was ineffective in adequately communicating with 

him regarding plea negotiations. That below-par performance, says 

Ortiz, cost him a better plea deal because it was off the table by 

the time his new counsel took over his case. Ortiz, in several 

pro se filings and through memoranda filed by his second attorney, 
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attempted to have the district court consider the detrimental 

impact of his first attorney's alleged deficient performance on 

the posture of his plea negotiations and resolve the ineffective 

assistance claim prior to sentencing. However, the district court 

refused to rule on his claim, finding it premature. Because it is 

clear that the district court seemingly misunderstood its 

authority to promptly decide Ortiz's Sixth Amendment claim that 

is, at least on its face, plausible because Ortiz raised his 

complaint about counsel's inadequate attention before signing the 

plea agreement, and because the terms of the plea agreement are 

themselves arguably a product of a Sixth Amendment violation, we 

believe that Ortiz's waiver falls into that narrow category of 

cases we described in Teeter where enforcement would work a 

miscarriage of justice. Therefore, we exercise our discretion not 

to enforce the waiver here. See United States v. Del Valle-Cruz, 

785 F.3d 48, 57 (1st Cir. 2015) (refusing to enforce a waiver where 

the error was of a "constitutional dimension"). We proceed to the 

merits of Ortiz's appeal. 

 2. Ineffective Assistance 

It is well-established that a defendant is entitled to 

the Sixth Amendment right to effective assistance of counsel during 

plea negotiations. United States v. Márquez-Pérez, 835 F.3d 153, 

165 (1st Cir. 2016). And "[w]e assess a claim of ineffectiveness 

in plea negotiations under the two-part test of Strickland v. 
- 18 - 

Washington, 466 U.S. 668 (1984), under which a defendant must show 

deficient performance and prejudice." Id. Deficient performance 

is measured against an "objective standard of reasonableness" and 

"[p]rejudice exists if there is a 'reasonable probability that, 

but for counsel's unprofessional errors, the result of the 

proceeding would have been different.'" Id. (quoting Strickland, 

466 U.S. at 688). 

"When we receive ineffective assistance of counsel 

claims on direct appeal, we have three options:" (1), and most 

commonly, we can decline to hear such claims, allowing the 

appellant to raise the claim before the district court by means of 

a 28 U.S.C. § 2255 collateral attack; (2) in more rare instances 

we can rule on the merits of the claim on direct appeal where the 

facts are sufficiently developed; or (3) where "the record [] is 

not developed enough to decide the ineffective assistance of 

counsel claim on the merits, yet it does contain sufficient indicia 

of ineffectiveness in the plea agreements, the PSR, and the 

transcripts of the change of plea and sentencing hearings," we may 

remand the case for proceedings on the ineffective assistance claim 

without requiring the defendant to bring a separate collateral 

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

Cir. 2004). 

And while we have not previously ruled on the precise 

issue presented here (whether a district court should rule on an 
- 19 - 

ineffective assistance claim prior to sentencing and if so, under 

what circumstances), as noted by Ortiz, we have indicated in the 

context of claims involving attorney-client disputes that "[w]here 

the accused voices objections to appointed counsel, the trial court 

should inquire into the reasons for the dissatisfaction." United 

States v. Prochilo, 187 F.3d 221, 229 (1st Cir. 1999) (quoting 

United States v. Allen, 789 F.2d 90, 92 (1st Cir. 1986)). The 

failure to conduct such an inquiry constitutes an abuse of 

discretion. Id. at 229 ("In the case at bar the trial court, in 

an abuse of its discretion, denied the motions for continuance and 

for reconsideration without making inquiry into the accused's 

concerns . . . . Because no inquiry was made, this court has no 

basis in the record for sustaining the trial court's rulings. 

Accordingly, we are constrained by the Sixth Amendment to direct 

that Prochilo's conviction be set aside and that this case be 

remanded to the district court for further proceedings."). 

We have similarly held, within the context of alleged 

conflict of interest situations, "that the district court must 

inquire into each instance of joint representation of multiple 

defendants, and must advise each defendant of his right to separate 

counsel." United States v. Coneo-Guerrero, 148 F.3d 44, 47 (1st 

Cir. 1998). We therefore require trial courts to "inquire 

diligently whether [defendants] have discussed the risks with 

their attorney, and whether they understand that they may retain 
- 20 - 

separate counsel, or if qualified, may have such counsel appointed 

by the court and paid for by the government." United States v. 

Foster, 469 F.2d 1, 5 (1st Cir. 1972); see also United States v. 

Cardona-Vicenty, 842 F.3d 766, 772 (1st Cir. 2016), cert. denied, 

137 S. Ct. 1238 (2017) ("[G]iven the 'ubiquitous and insidious' 

risks of multiple representation, the Sixth Amendment imposes a 

duty on trial courts to investigate a defendant's timely objections 

to joint representation and to inquire into the propriety of 

multiple representation whenever the trial court 'knows or 

reasonably should know that a particular conflict exists.'" 

(quoting United States v. Hernandez-Lebron, 23 F.3d 600, 603-04 

(1st Cir. 1994))). Accordingly, the importance of a district 

court's inquiry into attorney-client disputes and conflicts of 

interest is well established. 

Two of our sister circuits have ruled on the precise 

issue presented here. See United States v. Steele, 733 F.3d 894, 

897 (9th Cir. 2013); United States v. Brown, 623 F.3d 104, 112-14 

(2d Cir. 2010). In Brown, the Second Circuit held that the 

district court should have ruled on an ineffective assistance claim 

prior to sentencing where the defendant's first counsel (who had 

been accused of ineffective assistance) had already been relieved 

and the defendant was asserting that his previous counsel failed 

to inform him of a 20-year plea offer. 623 F.3d at 112-14 ("As a 

matter of first impression, we hold that when a claim of 
- 21 - 

ineffective assistance of counsel is first raised in the district 

court prior to the judgment of conviction, the district court may, 

and at times should, consider the claim at that point in the 

proceeding" and there was "no good reason to postpone inquiry into 

the merits of [the defendant's] claim."). 

The Second Circuit recognized that while the appellate 

court typically does not hear ineffective assistance claims on 

direct appeal (unless the record is sufficiently developed), a 

trial court need not invoke the "appellate court's rubric and 

require a defendant to use his one § 2255 motion to raise an 

ineffective assistance claim post-judgment, particularly when the 

district court is in a position to take evidence, if required, and 

to decide the issue pre-judgment." Id. at 113. 

The Ninth Circuit has since adopted the Second Circuit's 

holding, "adopt[ing] the rule in Brown that 'when a claim of 

ineffective assistance of counsel is first raised in the district 

court prior to the judgment of conviction, the district court may, 

and at times should, consider the claim at that point in the 

proceeding.'" Steele, 733 F.3d at 897 (quoting Brown, 623 F.3d at 

113) ("Though district courts have heard prejudgment ineffective 

assistance of counsel claims on occasion, see, e.g., United States 

v. Del Muro, 87 F.3d 1078, 1080 (9th Cir. 1996), we have not 

previously articulated the standard a district court should apply 

to decide whether to rule on such a claim. We agree with the 
- 22 - 

Second Circuit's decision in United States v. Brown, that a 

district court need not 'invoke an appellate court's rubric and 

require a defendant to use his one § 2255 motion to raise an 

ineffective assistance claim post judgment, particularly when the 

district court is in a position to take evidence, if required, and 

to decide the issue prejudgment.'" (quoting Brown, 623 F.3d at 

113)). Nevertheless, in Steele, the Ninth Circuit affirmed the 

district court's decision to reserve ruling on a defendant's 

ineffective assistance claim until after the initiation of 

collateral proceedings because of "the lack of a significant record 

necessary to adequately consider [the defendant's] broad-based 

motion" and the court's consideration of "delaying the trial 

proceedings to conduct an immediate hearing on an under-developed 

motion." Steele, 733 F.3d at 899. 

We agree with our sister circuits and similarly hold 

that "when a claim of ineffective assistance of counsel is first 

raised in the district court prior to the judgment of conviction, 

the district court may, and at times should, consider the claim at 

that point in the proceeding." Brown, 623 F.3d at 113. And the 

court's failure to do so may constitute an abuse of discretion. 

See id. at 112 ("The government argues unconvincingly that given 

the Supreme Court's and this Court's general aversion to deciding 

ineffective assistance claims on direct review, 'the district 

court's refusal to entertain [the defendant's] motion before he 
- 23 - 

was sentenced cannot be deemed an abuse of discretion.' We 

disagree."). 

As noted by the Second Circuit, "[w]e are mindful that 

district courts face competing considerations in deciding whether 

it is appropriate to inquire into the merits of such claims prior 

to judgment, including principally the potential disruption of the 

proceedings, especially if the attorney against whom the complaint 

is directed continues at the time to represent the defendant." 

Id. at 113. We similarly observe that "[t]he decision to interrupt 

the pre-judgment proceedings to inquire into the merits of an 

ineffective assistance of counsel claim may depend on, among other 

things, whether the court would need to relieve the defendant's 

attorney, or in any event, to appoint new counsel in order to 

properly adjudicate the merits of the claim." Id. The court may 

also take into consideration whether the defendant's "claim [is] 

broad-based and the evidentiary record to consider it [is] sorely 

lacking," as well as "whether the interests of justice and judicial 

economy would be served by delaying the trial proceedings to 

conduct an immediate hearing on an under-developed motion." 

Steele, 733 F.3d 898-99. 

Having outlined the proper standards applicable, we now 

turn to the particular facts of Ortiz's case. Ortiz argues that 

his first counsel was ineffective in failing to timely communicate 

that his counteroffer had been rejected, that the original plea 
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offer had expired, and by failing to adequately communicate 

concerning plea negotiations whatsoever after Ortiz made an 

initial counteroffer. 

As we detailed earlier, Ortiz raised his concerns at 

multiple points in the proceeding, providing the district court 

with several opportunities to address Ortiz's ineffective 

assistance claim. Based upon the facts of this case, we conclude 

that the district court had "no good reason to postpone inquiry 

into the merits of [Ortiz's] claim" and thus abused its discretion 

in doing so. Brown, 623 F.3d at 113. 

Like Brown, the only proceeding that would have been 

postponed or interrupted by an inquiry into the alleged 

ineffectiveness during plea negotiations would have been 

sentencing and the attorney against whom the complaint was directed 

(Dolz) had already been relieved of his duties since July 2012. 

Furthermore, the court had already scheduled and heard detailed 

arguments on the issue, rescheduling several sentencing hearings 

as needed. Additionally, unlike Steele, the record was 

significantly developed by the time of sentencing, especially 

since the district court had heard from both sides and had required 

both Dolz and the government to turn over their case files 

detailing the facts surrounding plea negotiations.11 Consequently, 

 11 We note that when Rivera attempted to call Dolz as a witness 

during one of the hearings, Dolz refused to take the stand, 
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the district court was well-positioned to decide the merits of 

Ortiz's claim without a sacrifice to judicial economy. 

In addition to these procedural considerations, there 

were also several factors indicating the facial plausibility of 

Ortiz's ineffective assistance claim including: the parties' 

dispute regarding how often Dolz communicated with Ortiz and the 

nature of those communications; the lack of clarity around when 

the original 130-147 month offer expired; Ortiz's consistent 

statements that he always desired to accept a plea and was only in 

search of the best deal; and Ortiz's assertion that Dolz never 

fully explained the nature of the offenses lodged against him 

during the course of negotiations.12 

As the Supreme Court has noted, the "plea-bargaining 

process is often in flux, with no clear standards or timelines and 

with no judicial supervision of the discussions between 

prosecution and defense." Missouri v. Frye, 566 U.S. 133, 143 

(2012). Yet, "[n]inety-seven percent of federal convictions and 

ninety-four percent of state convictions are the result of guilty 

pleas." Id. With such wide-sweeping impact despite the existence 

 

claiming he had a conflict, presumably with Ortiz. We are puzzled 

as to how such a conflict would excuse him from testifying in this 

circumstance. 

12 We also note that the record indicates that Dolz was ill 

at some point during his representation of Ortiz and was "out of 

commission" for at least ninety days. 
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of ambiguity around the standards to be maintained in the pleabargaining process, it may be imperative for a district court, at 

times, to rule on a claim of ineffective assistance prior to the 

defendant seeking post-conviction relief. Such is true here. If 

Dolz were found to have provided ineffective assistance in his 

failure to communicate with Ortiz during plea negotiations, the 

district court would be required to place Ortiz in the position he 

would have been had Dolz been effective. See Brown, 623 F.3d at 

114 ("[I]f counsel is determined to have been ineffective, equities 

require that the defendant be put in the same place he would have 

been but for counsel's ineffective assistance."). In other words, 

if the district court had determined that counsel's 

ineffectiveness caused Ortiz to be unaware of a plea offer that he 

would have accepted had he a chance to do so, then the district 

court should have given Ortiz that chance. On the other hand, if 

the court had determined that Dolz was not ineffective (as a 

reminder, to establish ineffective assistance Ortiz must 

demonstrate both deficient performance and that he was prejudiced 

by that performance), then Ortiz would have been stuck with the 

plea agreement he actually entered into. 

Conclusion 

Having determined that the district court abused its 

discretion in failing to rule on the merits of Ortiz's ineffective 

assistance claim prior to sentencing, we remand for further 
- 27 - 

proceedings consistent with this decision and retain jurisdiction 

over any remaining claims.13 

 13 Because we remand for further proceedings, we need not 

decide now Ortiz's sentencing disparity claim. See United States 

v. González-Vélez, 466 F.3d 27, 38 (1st Cir. 2006) (declining to 

rule on the merits of an appellant's other sentencing claims after 

remanding on the basis of one of his claims).