“We have held many times that reasonably effective representation cannot and does not include a requirement to make arguments based on predictions of how the law may develop.” (internal quotation marks omitted)
How later courts described this case
- “We have held many times that reasonably effective representation cannot and does not include a requirement to make arguments based on predictions of how the law may develop.” (internal quotation marks omitted)
- “[D]efendants are not entitled to an attorney capable of foreseeing the future development of constitutional law.”
Written by the judges who cited it.
The opinion
SUONUITTEHDE RSTNA DTIESTS RDIICSTTR OIFC TF LCOORUIRDTA
WEST PALM BEACH DIVISION
CASE NO. 22-81069-CIV-CANNON/McCabe
(CASE NO. 21-80026-CR-CANNON)
EMILIO SANTIAGO,
Movant,
v.
UNITED STATES OF AMERICA
Respondent.
/
ORDER ACCEPTING REPORT OF MAGISTRATE JUDGE WITH ADDITIONS
AND DENYING MOTION TO VACATE
THIS CAUSE comes before the Court upon the Report and Recommendation (“Report”)
[ECF No. 18] issued by Magistrate Judge Ryan M. McCabe, recommending denial of the Motion
to Vacate filed by Emilio Santiago (“Movant”) pursuant to 28 U.S.C. § 2255 [ECF No. 1].1
Movant timely filed Objections to the Report (the “Objections”) [ECF No. 23]. The Court has
reviewed the Report [ECF No. 18], the Objections [ECF No. 23], and the full record. For the
reasons set forth below, the Court ACCEPTS the Report as supplemented herein.
I. RELEVANT BACKGROUND
In February 2021, a Southern District of Florida grand jury returned an indictment charging
Movant with the following three drug-related offenses: (1) one count of conspiracy to possess with
intent to distribute 400 grams or more of fentanyl, in violation of 21 U.S.C. §§ 846 and
841(b)(1)(A)(vi) (Count 1); and (2) two counts of possession with intent to distribute 400 grams
or more of fentanyl, in violation of 21 U.S.C. § 841(b)(1)(A)(vi) (Counts 3 and 5)
1 Filings in the instant civil docket, 22-cv-81069, will be designated by [ECF], whereas filings in
the underlying criminal case, 21-cr-80026, will be designated by [CR ECF].
[CR ECF No. 44]. Movant pled guilty to Count 1 pursuant to a written plea agreement and factual
proffer [CR ECF No. 105].
Prior to sentencing, the Government filed a Notice of Filing Certified Convictions for
purposes of supporting Movant’s designation as a career offender under Section 4B1.1 of the
United States Sentencing Guidelines [CR ECF No. 163]. The Notice cited the following three
“controlled substance [predicate] offenses”: (1) Movant’s 2002 conviction for sale of cocaine, in
Florida state case number 02-13898-CF, (2) Movant’s 2001 conviction for sale of cocaine within
1,000 feet of a place of worship, in Florida case number 01-6895-CF, and (3) Movant’s 2010
conviction for possession with intent to distribute heroin in Southern District of Florida case
number 10-80098-CR [CR ECF No. 163 (and attachments)]. Defendant conceded in his
sentencing memorandum that he qualified as a career offender, and he did not object to the Pre-
Sentence Investigation Report designating him as such [CR ECF No. 150 ¶ 12; CR ECF No. 165
¶¶ 99, 122; CR ECF No. 167 ¶¶ 13–15].
On October 25, 2021, the Court sentenced Movant to 240 months’ imprisonment on Count
1 followed by five years’ supervised release [CR ECF No. 174]. The sentence represented a
downward variance from the uncontested advisory guideline range of 262 to 327 months’
imprisonment established at sentencing [CR ECF No. 242 pp. 4, 16–17 (Tr. Sentencing)].
Consistent with the waiver of appellate rights in his plea agreement, Movant did not appeal his
sentence [CR ECF No. 105 ¶ 8; CR ECF No. 243 pp. 16–19]. And the Government dismissed
Counts 3 and 5 at sentencing [ECF No. 174; ECF No. 242 p. 18].
On July 21, 2022, Movant filed the instant timely Motion to Vacate [ECF No. 1]. The
Motion advances the following two grounds for relief, both based on alleged ineffective assistance
of counsel in connection with his designation as a career offender under the Sentencing Guidelines:
(1) The offense to which Movant pled guilty, Count 1, was not a “controlled substance
offense” under U.S.S.G. § 4B1.1, making him ineligible for the career offender
enhancement.
(2) Two of Movant’s underlying state court convictions for cocaine-related offenses did
not qualify as “controlled substance offense[s]” under U.S.S.G. § 4B1.1, rendering
Movant ineligible for the career offender enhancement.
The Court referred the Motion to Magistrate Judge Ryon M. McCabe for a report and
recommendation [ECF No. 17]. On December 22, 2022, Judge McCabe issued the instant Report,
recommending denial of the Motion [ECF No. 18]. Following the Report, the Eleventh Circuit
decided United States v. Dupree, 57 F.4th 1269 (11th Cir. Jan. 18, 2023) (en banc), holding that
the term “controlled substance offense” in Section 4B1.2(b) “unambiguously excludes inchoate
offenses.” Id. at 1277 (overruling United States v. Smith, 54 F.3d 690 (11th Cir. 1995)). Movant
relies on Dupree in his Objections to the Report [ECF No. 23].
II. LEGAL STANDARDS
A. Review of Report and Recommendation
To challenge the findings and recommendations of a magistrate judge, a party must file
specific written objections identifying the portions of the proposed findings and recommendation
to which objection is made. See Fed. R. Civ. P. 72(b)(3); Heath v. Jones, 863 F.2d 815, 822 (11th
Cir. 1989); Macort v. Prem, Inc., 208 F. App’x 781, 784 (11th Cir. 2006). A district court may
accept, reject, or modify in whole or in part, the findings or recommendations made by the
magistrate judge. 28 U.S.C. § 636(b)(1). To the extent a party fails to object to parts of the
magistrate judge’s report, the Court may accept the recommendation so long as there is no clear
error on the face of the record. Macort, 208 F. App’x at 784. Legal conclusions are reviewed de
novo, even in the absence of an objection. See LeCroy v. McNeil, 397 F. App’x 554, 556 (11th
Cir. 2010); Cooper-Houston v. S. Ry. Co., 37 F.3d 603, 604 (11th Cir. 1994).
B. 28 U.S.C. § 2255
Pursuant to 28 U.S.C § 2255, a prisoner in federal custody may move the court that imposed
a sentence to vacate, set aside, or correct the sentence if it was imposed in violation of federal
constitutional or statutory law, was imposed without proper jurisdiction, is in excess of the
maximum authorized by law, or is otherwise subject to collateral attack. 28 U.S.C. § 2255(a).
Relief under Section 2255 “is reserved for transgressions of constitutional rights and for that
narrow compass of other injury that could not have been raised on direct appeal and would, if
condoned, result in a complete miscarriage of justice.” Lynn v. United States, 365 F.3d 1225, 1232
(11th Cir. 2004) (internal quotation marks omitted).
To show ineffective assistance of counsel, a movant must satisfy a two-part test: (1) the
movant must show that defense counsel’s performance was deficient; and (2) the movant must
show that the deficient performance prejudiced the defense. Strickland v. Washington, 466 U.S.
668, 687 (1984). To prove deficient performance, the movant must demonstrate that counsel’s
performance fell below an objective standard of reasonableness as measured by prevailing
professional norms. Id. at 688. Courts must “indulge a strong presumption that counsel’s conduct
falls within the wide range of reasonable professional assistance.” Id. at 689. To prove prejudice,
the movant “must show that there is a reasonable probability that, but for counsel’s unprofessional
errors, the result of the proceeding would have been different.” Id. at 694. A reasonable
probability is “a probability sufficient to undermine confidence in the outcome.” Id.
III. DISCUSSION
A. Ground I
In Ground I, citing to the Eleventh Circuit’s decision in Dupree, 57 F.4th at 1279, Movant
challenges his trial counsel’s decision at sentencing not to challenge Movant’s designation as a
career offender under U.S.S.G. § 4B1.1 [ECF No. 1-1 pp. 6–9]. More specifically, Movant argues
that the offense to which he pled guilty (the “instant offense of conviction”) is not a “controlled
substance offense” following Dupree, thus rendering invalid his previously unobjected-to
designation as a career-offender.
For a defendant to be classified as a career offender, “the instant offense [must be] a felony
that is either a crime of violence or a controlled substance offense.” U.S.S.G. § 4B1.1. At the
time Movant was sentenced on October 22, 2021 [CR ECF No. 174], binding Eleventh Circuit law
dictated that Movant’s instant offense, in this case, conspiracy to possess with intent to distribute
400 grams or more of fentanyl in violation of 21 U.S.C. § 846 (Count 1), qualified as a “controlled
substance offense.” United States v. Smith, 54 F.3d 690, 693 (11th Cir. 1995). No party challenged
the “controlled substance” offense nature of Count 1 at sentencing [CR ECF No. 150 p. 3;
CR ECF No. 165 ¶ 99; CR ECF No. 165-1 p. 1; CR ECF No. 167 p. 3].
In light of binding precedent in effect at Movant’s sentencing, the Report recommends
denial of Ground I [ECF No. 18 p. 6 (noting Smith)]. The Court accepts the conclusion in the
Report after review of the matter de novo and consideration of Movant’s objection based on
Dupree. It is true that, if Dupree had been decided at the time of Movant’s sentencing, Movant’s
“instant offense of conviction” (Count 1) would not have been deemed a “controlled substance
offense”’ in Section 4B1.2(b).2 But Dupree was not the law at the time—Smith was—and under
2 Judgment was entered against Movant on October 22, 2021, making his deadline to file a notice
of appeal November 8, 2021. See Fed. R. Crim. P. 4(b)(1)(A)(i). The Eleventh Circuit’s en banc
decision in Dupree was issued on January 18, 2023, months after Movant’s conviction became
Smith, Count 1 clearly qualified as a “controlled substance offense.” Smith, 54 F.3d at 693.
Movant’s counsel cannot be deemed constitutionally ineffective for failing to object to a
designation that was dictated by binding law at the time of the allegedly deficient performance
[ECF No. 23 p. 3–4]. See Spaziano v. Singletary, 36 F.3d 1028, 1039 (11th Cir. 1994) (“We have
held many times that reasonably effective representation cannot and does not include a requirement
to make arguments based on predictions of how the law may develop.” (internal quotation marks
omitted)); Thompson v. Wainwright, 787 F.2d 1447, 1459 n.8 (11th Cir. 1986) (“[D]efendants are
not entitled to an attorney capable of foreseeing the future development of constitutional law.”);
United States v. Ardley, 273 F.3d 991, 993 (11th Cir. 2001) (Carnes, J. concurring) (“That rule
applies even if the claim based upon anticipated changes in the law was reasonably available at
the time counsel failed to raise it.”).
B. Ground II
In Ground II, also on the subject of his career offender designation, Movant alleges that
counsel performed deficiently because his 2001 and 2002 Florida state convictions for sale of
cocaine, in violation of Fla. Stat. § 893.13(1),3 purportedly do not qualify as “controlled substance
offenses” following the Eleventh Circuit’s now-vacated decision in United States v. Jackson, 36
F.4th 1294 (11th Cir. 2022) [ECF No. 1-1 p. 12 (citing Jackson, 36 F.4th 1294, vacated, No.
21-13963, 2022 WL 4959314 (11th Cir. Sept. 8, 2022), and superseded, 55 F.4th 846 (11th Cir.
2022), cert. granted, 143 S. Ct. 2457 (2023))]. The Report concludes that Movant cannot meet
either prong of the Strickland test on this ground because Eleventh Circuit law at the time of
final. 57 F.4th at 1269. Dupree is not retroactively applicable on collateral review. 28 U.S.C.
§ 2244(b)(2)(A). And under the recently promulgated version of the Sentencing Guidelines
Manual, “inchoate offenses” are specifically included in the definition of “controlled substance
offenses.” U.S.S.G. § 4B1.2(d) (effective Nov. 1 2023).
3 [ECF Nos. 163-1, 163-2; ECF No. 165 ¶ 99]
sentencing—and still now—clearly holds that violations of Fla. Stat. § 893.13(1) qualify as
“controlled substance offenses” under Section 4B1.2(b) [ECF No. 18 pp. 8–9 (citing United States
v. Pridgeon, 853 F.3d 1192, 1197–98 (11th Cir. 2017), and United States v. Howard, 767 F. App’x
779, 785 (11th Cir. 2019)].
For a defendant to qualify as a career offender under Section 4B1.1, he must have “at least
two prior felony convictions of either a crime of violence or a controlled substance offense,”
among other requirements. U.S.S.G. § 4B1.1(a). A “controlled substance offense” is defined as:
an offense under federal or state law, punishable by imprisonment for a term
exceeding one year, that prohibits the manufacture, import, export, distribution, or
dispensing of a controlled substance (or a counterfeit substance) or the possession
of a controlled substance (or a counterfeit substance) with intent to manufacture,
import, export, distribute, or dispense . . . .
U.S.S.G. § 4B1.2(b).
Reviewing the issue de novo, the Report correctly determines that Movant has not
demonstrated deficient performance on the part of his counsel in acknowledging at sentencing
what binding law dictated (and still dictates): that Movant’s prior convictions for sale of cocaine
counted as “controlled substance offenses” under § 4B1.2(b). As Movant essentially
acknowledges in his Objections, any argument based on Jackson I no longer applies following the
Eleventh Circuit’s decision vacating Jackson I [ECF No. 23 p. 4]. United States v. Jackson, 55
F.4th 846, 861–62 (11th Cir. 2022), cert. granted, 143 S. Ct. 2457 (2023). In any event, even if
Jackson I remained in force, the Report accurately observes that Jackson I concerned the definition
of the term “serious drug offense” in the Armed Career Criminal Act (“ACCA”)—not the distinct
definition of “controlled substance offense” in U.S.S.G. § 4B1.1. See U.S.S.G. § 4B1.4 cmt. n.1
(“It is to be noted that the definitions of ‘violent felony’ and ‘serious drug offense’ in 18 U.S.C.
§ 924(e) are not identical to the definitions of ‘crime of violence’ and ‘controlled substance
offense’ used in § 4B1.1 (Career Offender) . . . .”). Unlike the career offender provision in the
Sentencing Guidelines pursuant to which Movant was sentenced, the ACCA expressly
incorporates the federal Controlled Substances Act (“CSA”) in defining “serious drug offense.”
Compare 18 U.S.C. § 924(e)(2)(A)(i) (explaining that “serious drug offense” means inter alia “an
offense under the [CSA]”) with U.S.S.G. § 4B1.2(b). Accordingly, the rationale of Jackson I
would not have operated to invalidate Movant’s designation as a career offender pursuant to
U.S.S.G. § 4B1.1. And the record is undisputed that Movant has two prior convictions for the sale
of cocaine, in violation of Fla. Stat. § 893.13(1)(a) [CR ECF No. 165 ¶ 99; ECF Nos. 163-1, 163-
2]. For these reasons, under Eleventh Circuit precedent at the time of sentencing (October 2021)
and still now, a violation of Fla. Stat. § 893.13(1) qualifies as a “controlled substance offense”
under U.S.S.G. § 4B1.1. See, e.g., United States v. Pridgeon, 853 F.3d 1192, 1197–98 (11th Cir.
2017); United States v. Smith, 775 F.3d 1262, 1268 (11th Cir. 2014); United States v. Agerton, No.
22-10194, 2023 WL 5537057, at *5 (11th Cir. Aug. 29, 2023) (citing United States v. Penn, 63
F.4th 1305, 1317 (11th Cir. 2023)). Counsel was not ineffective for failing to challenge the use of
Movant’s cocaine-related convictions to support his career offender enhancement. Singletary, 36
F.3d at 1039; Smith, 775 F.3d at 1268.
IV. CERTIFICATE OF APPEALABILITY
A movant seeking to appeal a district court’s final order denying his motion to vacate must
obtain a certificate of appealability to do so. See 28 U.S.C. § 2253(c)(1)(B). The Court should
issue a certificate of appealability only if the movant makes “a substantial showing of the denial
of a constitutional right.” 28 U.S.C. § 2253(c)(2); Slack v. McDaniel, 529 U.S. 473, 484 (2000).
Reasonable jurists would not find the Court’s assessment of Grounds I or II debatable or wrong.
WLLL INV. L2L7OLYUUIOKWW LV OCU SALNINNZL AU
V. CONCLUSION
Accordingly, it is ORDERED AND ADJUDGED as follows:
1. The Court ACCEPTS Magistrate Judge McCabe’s Report and Recommendation
[ECF No. 18] as supplemented herein following Movant’s Objections.
2. No Certificate of Appealability shall issue.
3. Movant’s Motion to Stay [ECF No. 21], Motion to Withdraw Motion to Stay
[ECF No. 22], and Motion for Evidentiary Hearing and Motion to Appoint Counsel
[ECF No. 24] are DENIED as moot.
4. An evidentiary hearing is not warranted on Grounds I or II. See 28 U.S.C. § 2255(b)
(providing that no evidentiary hearing is required where “the motion and the files and
the records of the case conclusively show that the prisoner is entitled to no relief”).
5. This Clerk is directed to CLOSE this case.
DONE AND ORDERED in Chambers at Fort Pierce, Florida this 7th day of November
2023.
Cy. M. CANNON
UNITED STATES DISTRICT JUDGE
ce: Counsel of record
Emilio Santiago
73790-004
Edgefield
Federal Correctional Institution
Inmate Mail/Parcels
Post Office Box 725
Edgefield, South Carolina 29824
PRO SE