Rivera-Toledo v. United States

UNITED STATES DISTRICT COURT

MIDDLE DISTRICT OF FLORIDA

TAMPA DIVISION

HAROLD DARIO RIVERA-TOLEDO,

Prisoner,

v. Case No. 8:23-cv-2271−KKM−SPF

Case No. 8:21-cr-217-KKM-AAS

UNITED STATES OF AMERICA,

Respondent.

____________________________________

ORDER

Prisoner Harold Dario Rivera-Toledo moves to vacate his conviction and

sentence for conspiracy to distribute and possess with intent to distribute cocaine

while on board an aircraft registered with the United States, for which he serves a

120-month sentence. See 28 U.S.C. § 2255. Rivera-Toledo claims his counsel

rendered constitutionally ineffective assistance. Because his claims lack merit, his

motion to vacate is denied.

I. Background

In May 2021, Rivera-Toledo left Guaymaral, Colombia, on board an aircraft

registered with the United States on a purported humanitarian mission trip to

Providencia Island, Colombia. (Crim. Doc. 94 at 20–21.) Upon arrival, the

Colombian National Police inspected 28 boxes on board the aircraft and found 446

kilograms of cocaine. (Id.)

In July 2021, Rivera-Toledo and three others were charged in a four-count

superseding indictment with conspiring to distribute five kilograms or more of

cocaine knowing, intending, and having reasonable cause to believe that such

cocaine would be unlawfully imported into the United States, in violation of 21

U.S.C. §§ 959(a), 969, and 960(b)(1)(B)(ii) (Count One); conspiring to possess five

kilograms or more of cocaine with the intent to distribute it while on board an

aircraft registered with the United States, in violation of 21 U.S.C. §§ 959(c)(1),

(c)(2), 963, and 960(b)(1)(B)(ii) (Count Two); and two counts of possessing with the

intent to distribute cocaine while on board an aircraft registered with the United

States, in violation of 21 U.S.C. § 959(c)(2) and 960(b)(1)(B)(ii), and 18 U.S.C. § 2

(Counts Three and Four). (Crim. Doc. 8.) Under a plea agreement, Rivera-Toledo

agreed to plead guilty to Count Two in exchange for the United States moving to

dismiss the remaining counts against him. (Crim. Doc. 94 at 1 and 3.)

The presentence report calculated an advisory guidelines range of 135 to 168

months based on Rivera-Toledo’s total offense level of 33 and his criminal history

category of I. (Crim. Doc. 122 at ¶ 72.) Citing Rivera-Toledo’s role in the offense,

the district court varied downward from the guidelines range and sentenced him

to 120 months. (Crim. Docs. 131 and 132.) Rivera-Toledo filed no appeal.

He now moves to vacate his conviction and sentence and claims that counsel

was ineffective for (1) not obtaining safety-valve relief and (2) not obtaining

discovery materials. (Civ. Doc. 3 at 4–5 and Civ. Doc. 11.)

II. Legal Standards

Section 2255 allows a federal prisoner to “bring a collateral challenge by

moving the sentencing court to vacate, set aside, or correct the sentence.”

Winthrop-Redin v. United States, 767 F.3d 1210, 1215–16 (11th Cir. 2014). But “[o]nce

the defendant’s chance to appeal has been waived or exhausted, [a court is]

entitled to presume he stands fairly and finally convicted, especially when . . . he

already has had a fair opportunity to present his federal claims to a federal forum.”

United States v. Frady, 456 U.S. 152, 164 (1982). “[A] collateral challenge, such as a

§ 2255 motion, may not be a surrogate for a direct appeal.” Lynn v. United States,

365 F.3d 1225, 1232 (11th Cir. 2004) (per curiam) (citing Frady, 456 U.S. at 165).

Because collateral review is not a substitute for direct appeal, a defendant must

raise on direct appeal all available claims. Relief under § 2255 is reserved “for

transgressions of constitutional rights and for that narrow compass of other injury

that could not have been raised in direct appeal and would, if condoned, result in

a complete miscarriage of justice.’” Richards v. United States, 837 F.2d 965, 966 (11th

Cir. 1988) (quoting United States v. Capua, 656 F.2d 1033, 1037 (5th Cir. Unit A Sep.

1981)). For example, a claim of ineffective assistance of counsel is a claim that

“should usually be raised in a motion under 28 U.S.C. § 2255.” United States v.

Curbelo, 726 F.3d 1260, 1267(11th Cir. 2013).

“[T]he cases in which habeas petitioners can properly prevail on the ground

of ineffective assistance of counsel are few and far between.” Waters v. Thomas,

46 F.3d 1506, 1511 (11th Cir. 1995) (en banc) (quoting Rogers v. Zant, 13 F.3d 384,

386 (11th Cir. 1994)). The well-known Strickland standard continues to govern an

ineffective assistance of counsel claim:

In Strickland v. Washington, 466 U.S. 668, 104 S. Ct. 2052,

80 L. Ed. 2d 674 (1984), the Supreme Court set forth a two-

part test for analyzing ineffective assistance of counsel claims.

According to Strickland, first, the defendant must show that

counsel’s performance was deficient. This requires showing

that counsel made errors so serious that counsel was not

functioning as the “counsel” guaranteed the defendant by the

Sixth Amendment. Second, the defendant must show that the

deficient performance prejudiced the defense. This requires

showing that counsel’s errors were so serious as to deprive

the defendant of a fair trial, a trial whose result is reliable.

Strickland, 466 U.S. at 687, 104 S. Ct. 2052.

Sims v. Singletary, 155 F.3d 1297, 1305 (11th Cir. 1998).

Strickland requires proof of both deficient performance and consequent

prejudice. Strickland, 466 U.S. at 697 (“There is no reason for a court deciding an

ineffective assistance claim . . . to address both components of the inquiry if the

defendant makes an insufficient showing on one.”); Sims, 155 F.3d at 1305 (“When

applying Strickland, we are free to dispose of ineffectiveness claims on either of its

two grounds.”). “[C]ounsel is strongly presumed to have rendered adequate

assistance and made all significant decisions in the exercise of reasonable

professional judgment.” Strickland, 466 U.S. at 690. “[A] court deciding an actual

ineffectiveness claim must judge the reasonableness of counsel’s challenged

conduct on the facts of the particular case, viewed as of the time of counsel’s

conduct.” 466 U.S. at 690. Strickland requires that “in light of all the circumstances,

the identified acts or omissions were outside the wide range of professionally

competent assistance.” 466 U.S. at 690.

Rivera-Toledo must demonstrate that counsel’s alleged error prejudiced the

defense because “[a]n error by counsel, even if professionally unreasonable, does

not warrant setting aside the judgment of a criminal proceeding if the error had

no effect on the judgment.” 466 U.S. at 691–92. To meet this burden, Rivera-Toledo

must show “a reasonable probability that, but for counsel’s unprofessional errors,

the result of the proceeding would have been different. A reasonable probability

is a probability sufficient to undermine confidence in the outcome.” 466 U.S. at

694.

Strickland cautions that “strategic choices made after thorough investigation

of law and facts relevant to plausible options are virtually unchallengeable; and

strategic choices made after less than complete investigation are reasonable

precisely to the extent that reasonable professional judgments support the

limitations on investigation.” 466 U.S. at 690–91. A prisoner cannot meet his

burden merely by showing that the avenue chosen by counsel proved

unsuccessful.

The test has nothing to do with what the best lawyers would

have done. Nor is the test even what most good lawyers

would have done. We ask only whether some reasonable

lawyer at the trial could have acted, in the circumstances, as

defense counsel acted at trial . . . . We are not interested in

grading lawyers’ performances; we are interested in whether

the adversarial process at trial, in fact, worked adequately.

White v. Singletary, 972 F.2d 1218, 1220–21 (11th Cir. 1992); accord Chandler v. United

States, 218 F.3d 1305, 1313 (11th Cir. 2000) (“To state the obvious: the trial lawyers,

in every case, could have done something more or something different. So,

omissions are inevitable . . . . [T]he issue is not what is possible or ‘what is prudent

or appropriate, but only what is constitutionally compelled.’”) (en banc) (quoting

Burger v. Kemp, 483 U.S. 776, 794 (1987)); see also Jones v. Barnes, 463 U.S. 745, 751

(1983) (counsel has no duty to raise a frivolous claim).

III. Analysis

A. Ground One

Rivera-Toledo claims that counsel was ineffective at sentencing for

“ma[king] no attempt to secure safety valve relief[.]” (Civ. Doc. 3 at 4.) In his reply,

he clarifies his claim and concedes that counsel advocated for safety-valve relief

but complains that counsel “did not investigate into the reasoning as to why he

was denied the relief.” (Civ. Doc. 11 at 1.) He argues that counsel’s performance

resulted in “a longer than necessary sentence.” (Civ. Doc. 3 at 4.)

A district court may impose a sentence below the statutory mandatory

minimum if a defendant meets certain criteria under 18 U.S.C. § 3553(f). The

burden is on the defendant to show that he satisfies all the safety-valve factors. See

United States v. Johnson, 375 F.3d 1300, 1302 (11th Cir. 2004). One of the safety-valve

factors requires the defendant to show that he “has truthfully provided to the

Government all information and evidence [he] has concerning the offense or

offenses that were part of the same course of conduct or of a common scheme or

plan[.]” 18 U.S.C. § 3553(f)(5).

Rivera-Toledo is entitled to no relief on this claim because the record shows

that counsel vigorously advocated for safety-valve relief but was unsuccessful

because Rivera-Toledo could not show he provided truthful information about his

offenses to the United States. Defense counsel objected to the presentence report

and argued that Rivera-Toledo was entitled to both “safety valve [relief] upon

completion of his upcoming debrief” and “a minor role adjustment of 2 points.”

(Crim. Doc. 122 at ¶¶ 28 and 30 and p.20.) Counsel argued that Rivera-Toledo’s

“job was simply to load the containers of contraband,” “had no roll in the planning

of the offense,” and “is substantially less culpable than his coconspirators.” (Id.)

Counsel repeated this argument in a sentencing memorandum and argued, “Mr.

Toledo expects to have qualified for safety valve, which would give an additional

two point reduction and remove the ten year minimum mandatory he would

otherwise be subject to.” (Crim. Doc. 125 at 1 and 3.) Counsel further argued (id.

at 2–3):

Mr. Toledo’s sole activity in this case occurred on May 23,

2021, when he assisted corrupted local law enforcement [to]

load 28 boxes of contraband onto an airplane whose purpose

was originally humanitarian. PSI 5-6. He had no role in the

planning of the offense, he did not exercise discretion or

decision making authority. He didn’t plan it and there is no

evidence he knew the people involved in the planning and the

ultimate scope of the conspiracy. The quantity of drugs, the

money involved, equity interest in the drugs, and the role in

planning and distribution are relevant factors this court

should consider. See United States v. DeVaron, 175 F.3d 930, 945

(11th Cir. 1999).

The United States responded that Rivera-Toledo was not entitled to safety-

valve relief because he was not truthful with investigating agents during his

proffer. (Crim. Doc. 129 at 4–5.) Rivera-Toledo told the agents that he was hired to

travel on the aircraft the day before the departure and he knew little about the

purpose of the flight. (Id.) According to the United States, Rivera-Toledo was, in

fact, hired a week before the flight by the transportation organizer and was

specifically advised of the purpose of the flight. (Id.) He was hired as the load

guard in order “to confirm the entire shipment of drugs was delivered, and if not,

why not.” (Id.)

At sentencing, Special Agent Guzman with Homeland Security

Investigations testified that Rivera-Toledo lied during his proffer. (Crim. Doc. 162

at 24.) Guzman testified that Rivera-Toledo stated that he first learned cocaine was

on board the aircraft when police officers opened the boxes in Providencia Island.

(Id.) But Rivera-Toledo’s coconspirator, who had been cooperating with law

enforcement, advised that the two had been working together for eight years, and

Rivera-Toledo knew he would be paid from the profits of the cocaine sale. (Id. at

19 and 26.) The district court asked Guzman, “as far as you know from the proffer

last Friday, the defendant said he did not know that there was cocaine until after

the flight had ended and the boxes were opened?” (Id. at 27.) The agent responded,

“Yes.” (Id.)

Counsel continued to advocate for safety-valve relief. She suggested that

Toledo-Rivera’s proffered statement that he did not know the boxes contained

cocaine was not untruthful, but rather, the result of a cultural linguistic difference

(id. at 28–29):

I have found that among the Colombians them saying that

they know something specifically is a little bit different . . . .

[U]nless they see it, taste it, smell it, they are not willing to say

I now that that is cocaine or I know that this fellow did

something. . . . [F]or [Rivera-Toledo] to . . . say I know it was

cocaine when [he] didn’t see it, [he] didn’t smell it, . . . [he]

didn’t open the boxes, is a leap for [him] culturally.

Ultimately, the district court acknowledged “the cultural linguistic disparities,”

but denied safety-valve relief because Rivera-Toledo testified dishonestly during

the proffer (id. at 29 and 33):

I don’t think that Mr. Rivera-Toledo has truthfully provided

testimony to the government and, therefore, I don’t think he

is eligible for safety valve relief. In particular, I credit the

testimony of Special Agent Guzman in her testimony

concerning what the defendant knew and communications he

had with [Rivera-Toledo’s coconspirator] and, in particular,

his denial of knowing about drugs until after the flight had

concluded and the boxes were opened. So I don’t think he’s

entitled to safety valve relief for that reason.

Additionally, the district court denied Rivera-Toledo a minor-role reduction

because he was “held accountable for exactly the amount of cocaine that he

transported or assisted in transporting” and because “the evidence points to the

fact that he was operating in some manner as a load guard.” (Id. at 35.)

Rivera-Toledo cannot show that counsel performed deficiently by not

successfully advocating for safety-valve relief. “[The circuit court] has long held

that the fact that a particular defense was unsuccessful does not prove ineffective

assistance of counsel.” Ward v. Hall, 592 F.3d 1144, 1164 (11th Cir. 2010). The record

shows counsel repeatedly advocated for safety-valve relief and attempted to

recharacterize Rivera-Toledo’s proffer statements as the result of cultural

linguistic differences rather than as untruthful. Although the district court

ultimately overruled counsel’s objection to the presentence report, Rivera-Toledo

cannot show that “no competent counsel would have taken the action that his

counsel did take.” Chandler, 218 F.3d at 1315. Indeed, Rivera-Toledo does not

suggest what more counsel could have argued to support safety-valve relief.

Rivera-Toledo’s undeveloped claim “that a different strategy would have been

better does not meet his burden under Strickland.” Lukehart v. Sec’y, Fla. Dep’t of

Corr., 50 F.4th 32, 47 (11th Cir. 2022) (citing Ward, 592 F.3d at 1164 (“[C]ounsel

cannot be adjudged incompetent for performing in a particular way in a case, as

long as the approach taken might be considered sound trial strategy.”)).

Nor can Rivera-Toledo show he was prejudiced because he cannot satisfy

all the factors under 18 U.S.C. § 3553(f). To demonstrate prejudice, Rivera-Toledo

must show “a reasonable probability that the result of the proceeding—i.e., the

length of his sentence—would have been different absent counsel’s allegedly

deficient performance.” United States v. Simmons, 799 F. App’x 718, 722 (11th Cir.

2020) (citing Griffith v. United States, 871 F.3d 1321, 1330 (11th Cir. 2017)). The

record shows that Rivera-Toledo did not receive safety-valve relief not because of

counsel’s ineffectiveness but because, as stated by the district court, he did not

provide truthful testimony to the United States about his offenses. See Patton v.

United States, 259 F. App’x 194, 196 (11th Cir. 2007) (concluding petitioner could

not show prejudice when she could not satisfy one of the § 3553(f) factors); Rengifo-

Valencia v. United States, No. 19-14747-A, 2020 WL 13597893, at *1 (11th Cir. Apr. 2,

2020) (same). Accordingly, because Rivera-Toledo cannot satisfy all the § 3553(f)

factors, he cannot show he was prejudiced by counsel’s unsuccessful advocacy for

safety-valve relief.

B. Ground Two

Rivera-Toledo claims that counsel was ineffective for not providing him

“‘Brady materials’ that could have been in favor or against [him].” (Civ. Doc. 3 at

5.) In his reply, he clarifies that he does not claim that the United States violated

Brady v. Maryland, 373 U.S. 83, 86 (1953) (suppression of evidence favorable to a

defendant violates due process), but rather, that counsel should have obtained

records that showed his “actual duties and tasks at the airport in which he was

employed . . . as a baggage handler.” (Civ. Doc. 11 at 2.) Because counsel failed to

obtain these employment records, Rivera-Toledo argues, the United States

wrongly assumed he was a load guard. (Id.) He believes the records could have

shown that (1) his “only duty was to literally unload and load cargo[,]” and (2) his

proffer statements that he did not know cocaine was on board the aircraft were

truthful. (Civ. Doc. 11 at 3.) And, he argues that the records “could have possibly

resulted in a different outcome for a lesser sentence[.]”(Civ. Doc. 3 at 5.)

Rivera-Toledo’s claim fails because it is purely speculative. Rivera-Toledo

speculates that records exist that show both that he was employed in the legitimate

role of baggage handler and that his only role was to unload and load cargo.

However, “speculation is insufficient to carry the burden of a habeas corpus

petitioner as to what evidence could have been revealed by further investigation.”

See Brownlee v. Haley, 306 F.3d 1053, 1060 (11th Cir. 2002); see also Tejada v. Dugger,

941 F.2d 1551, 1559 (11th Cir. 1991) (recognizing that vague, conclusory, or

unsupported allegations cannot support an ineffective assistance of counsel

claim).

Furthermore, Rivera-Toledo cannot show he was prejudiced by counsel’s

performance in not obtaining records authenticating his legitimate employment as

baggage handler. Even if counsel obtained such records, Rivera-Toledo admitted

in the plea agreement (1) to loading 28 boxes that contained cocaine onto the

aircraft and (2) to “knowingly and willfully agree[ing] to transport 446 kilograms

of cocaine on board N722KR, a U.S. registered aircraft, from Guaymaral,

Colombia, to Providencia Island, Colombia, . . . with the intent to distribute it to

other people[.]” (Crim. Doc. 94 at 21.) Because he admitted to knowingly

transporting cocaine with the intent to distribute it, he cannot show “a reasonable

probability that the result of the proceeding—i.e., the length of his sentence—

would have been different” absent counsel’s failure to obtain his employment

records. See Simmons, 799 F. App’x at 722 (citing Griffith, 871 F.3d at 1330)). Even if

employment records substantiated Rivera-Toledo’s legitimate role as baggage

handler, he admitted to knowingly transporting cocaine and therefore was

ineligible for safety-valve relief because he was dishonest during his proffer when

he professed his ignorance of the cocaine.

C. Rivera-Toledo’s Reply

In his reply, Rivera-Toledo attempts to raise a new claim for the first time in

this action. Buried within his other arguments, he complains in two sentences that

“counsel was ineffective for not filing an appeal at the conclusion of sentencing”

and “counsel failed to file an appeal.” (Civ. Doc. 11 at 2 and 5.) Although a district

court is required to resolve every claim properly presented in a § 2255 motion,

Clisby v. Jones, 960 F.2d 925, 936 (11th Cir. 1992), the district court is not required

to address a claim that a party fails to raise until the reply. See United States v.

Howard, 28 F.4th 180, 201, n. 6 (11th Cir. 2022) (“Arguments raised for the first time

in a reply brief are not properly before a reviewing court.”) (quotations and

alterations omitted).

Rivera-Toledo raised no claim that counsel was ineffective for not appealing

in his initial § 2255 motion nor his amended § 2255 motion on which he currently

proceeds. (Civ. Docs. 1 and 3.) It is not until his reply that Rivera-Toledo first

complains that counsel was ineffective for not appealing. Therefore, by waiting

until his reply to advance this claim, it is not properly before the district court, and

the district court shall not consider it. See Wilson v. United States, No. 16-15133, 2017

WL 3225903, at *1 (11th Cir. Feb. 23, 2017) (citing Herring v. Sec’y, Dep’t of Corr., 397

F.3d 1338, 1342 (11th Cir. 2005) (“[T]his claim was not properly raised until [the]

reply brief and, therefore, was not properly before the district court.”)); see also

Prada v. United States, 692 F. App’x 572, 574 (11th Cir. 2017) (affirming the district

court’s refusal to consider new arguments raised in a reply brief because petitioner

“was barred from raising new claims”); Enriques v. United States, 416 F. App’x 849,

850 (11th Cir. 2011) (“Although pro se pleadings are construed more liberally than

those filed by counsel, . . . issues not argued by a pro se litigant in his initial brief

are deemed waived[,] . . . [and] we do not address arguments raised for the first

time in a pro se litigant’s reply brief.”); Snyder v. United States, 263 F. App’x 778,

780 (11th Cir. 2008) (affirming the district court’s ruling that a pro se petitioner’s

reply brief could not be construed as an amendment to add an additional claim to

the motion to vacate).

Additionally, in his reply, Rivera-Toledo attempts to resurrect a claim that

he first identified in his initial § 2255 motion but abandoned by excluding it from

his amended § 2255 motion. (Civ. Doc. 11 at 4.) He complains that counsel was

ineffective for not obtaining a zero-point offender downward adjustment under

U.S. Sentencing Guidelines § 4C1.1. Rivera-Toledo listed this as his third claim in

his initial § 2255 motion. (Civ. Doc. 1 at 2.) He then did not include it when he filed

an amended § 2255 motion. (Civ. Doc. 2.) In his amended § 2255 motion, Rivera-

Toledo pursues only two claims—that counsel was ineffective for not obtaining

safety-valve relief and for not obtaining his employment records. His operative

motion contains no claim concerning counsel’s failure to obtain a zero-point

offender downward adjustment.

“Under Rule 12 of the Rules Governing Section 2255 Proceedings, a district

court may apply the Federal Rules of Civil Procedure consistent with the Rules

Governing Section 2255 Proceedings.” Snyder, 263 F. App’x at 780 n.2. “An

amended pleading supersedes the former pleading; the original pleading is

abandoned by the amendment, and is no longer a part of the pleader’s averments

against his adversary.” Pintando v. Miami-Dade Housing Agency, 501 F. 3d 1241,

1243 (11th Cir. 2007) (quotations omitted and citing Fritz v. Standard Sec. Life Ins.

Co., 676 F.2d 1356, 1358 (11th Cir. 1982) (“Under the Federal Rules, an amended

complaint supersedes the original complaint.”)). Because Rivera-Toledo’s

amended § 2255 motion superseded his original § 2255 motion, the claim that

counsel was ineffective for not obtaining a zero-point offender downward

adjustment under § 4C1.1, which is absent from the amended § 2255 motion, is

abandoned.

IV. No Certificate of Appealability

Rivera-Toledo is not entitled to a certificate of appealability (COA). A

prisoner moving under § 2255 has no absolute entitlement to appeal a district

court’s denial of his motion to vacate. 28 U.S.C. § 2253(c)(1). Rather, a district court

must first issue a COA. Section 2253(c)(2) permits issuing a COA “only if the

applicant has made a substantial showing of the denial of a constitutional right.”

To merit a certificate of appealability, Rivera-Toledo must show that reasonable

jurists would find debatable both (1) the merits of the underlying claims and (2)

the procedural issues he seeks to raise. See 28 U.S.C. § 2253(c)(2); Slack v. McDaniel,

529 U.S. 473, 478 (2000); Eagle v. Linahan, 279 F.3d 926, 935 (11th Cir 2001). Because

he fails to show that reasonable jurists would debate either the merits of the claims

or the procedural issues, Rivera-Toledo is entitled to neither a certificate of

appealability nor an appeal in forma pauperis.

V. Conclusion

Rivera-Toledo’s amended motion under § 2255 to vacate, set aside, or

correct his sentence (Civ. Doc. 3) is DENIED and a certificate of appealability is

DENIED. Leave to appeal in forma pauperis is similarly DENIED. Rivera-Toledo

must obtain permission from the circuit court to appeal in forma pauperis. The

clerk is directed to enter a JUDGMENT against Rivera-Toledo, terminate any

pending motions, CLOSE this case, and enter a copy of this order in the criminal

case.

ORDERED in Tampa, Florida, on February 24, 2025.

athryn’ Kimball Mizelle

United States District Judge

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