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Estremera v. United States

United States District Court, D. Connecticut

September 22, 2017


          RULING ON MOTION PURSUANT TO 28 U.S.C. § 2255


         Petitioner Daniel Estremera, proceeding pro se, has filed a petition pursuant to 28 U.S.C. § 2255 to vacate, set aside or correct his sentence.[1] The petitioner claims that his prior convictions were insufficient to trigger an enhanced mandatory minimum penalty pursuant to 21 U.S.C § 851. For the reasons set forth below, the petitioner's contentions are without merit, and the motion is being denied without a hearing.


         In March 2007, a federal grand jury returned an Indictment charging the petitioner and 19 other defendants with conspiracy to possess with intent to distribute one kilogram or more of heroin in violation of 21 U.S.C. §§ 841(a)(1), 841(b)(1)(A)(i) and 846. On May 7, 2008, the government filed a second offender information pursuant to 21 U.S.C § 851, asserting that the petitioner had been convicted of three narcotics felonies in 1997 and 1998 and stating that the petitioner faced a term of imprisonment of up to life, a mandatory minimum term of 10 years in prison, a maximum fine of $4, 000, 000 and a mandatory term of supervised release of at least eight years.

         On May 8, 2008, the petitioner pled guilty to a substitute information charging him with conspiracy to possess with intent to distribute 100 grams or more of heroin. In his plea agreement, the petitioner agreed that, after the enhancement pursuant to Section 851, he faced a mandatory minimum term of 10 years of imprisonment and a Guidelines range of at least 120 months of imprisonment.

         The petitioner acknowledged in his plea agreement that his Guidelines range might be as high as 262 to 327 months of imprisonment, because, at the time he pled guilty, it appeared that the petitioner qualified as a career offender. The petitioner also expressly waived his right to appeal or collaterally attack his sentence if the sentence did not exceed 262 months of imprisonment.

         On September 18, 2008, the Second Circuit decided United States v. Savage, 542 F.3d 959 (2d Cir. 2008). In Savage, the court held that a federal defendant's prior conviction that was entered pursuant to an Alford plea, i.e. a plea in which a defendant is “unwilling or unable to admit his participation in the acts constituting the crime, ” could not categorically qualify as a “controlled substance offense, ” as that term is defined in Section 4B1.2(b) of the Guidelines, and, consequently, could not support a career offender enhancement under Section 4B1.1 of the Guidelines. Id. at 962, 964 (quoting North Carolina v. Alford, 400 U.S. 25, 37 (1970)).

         On February 10, 2009, the petitioner was sentenced. At sentencing, the government informed the court that it was clear that two of Estremera's prior convictions (Docket Nos. H14H-CR960496486S and H14H-CR970509267S) were the result of Alford pleas, so the government could not establish that Estremera was a career offender.

         Estremera was sentenced to a mandatory minimum term of 10 years of imprisonment, to be followed by an eight-year term of supervised release, on the charge contained in the substitute information. The petitioner did not appeal his sentence, and on February 21, 2009, the time period within which Estremera was required to file a direct appeal expired.

         On June 29, 2009, the government filed a sentencing memorandum in an unrelated case, i.e. United States v. Jackson, 3:06cr151 (MRK), acknowledging that the reasoning of Savage should be extended to apply to second offender enhancements under 21 U.S.C. § 851. On August 10, 2009, Judge Kravitz granted the government's motion to withdraw the § 851 second offender information that had been filed in the Jackson case, thus recognizing the legal basis for the claim Estremera appears to assert in his habeas petition.

         On February 21, 2010, the one-year statute of limitations on Estremera's right to file a habeas petition expired. On September 22, 2011, i.e. approximately 31 months after Estremera had been sentenced and 19 months after the statute of limitations on his habeas claim had run, Estremera filed the petition in Case No. 3:11cv1474.


         Federal prisoners can challenge a criminal sentence pursuant to 28 U.S.C. § 2255 only in limited circumstances.

[A] “collateral attack on a final judgment in a criminal case is generally available under § 2255 only for a constitutional error, a lack of jurisdiction in the sentencing court, or an error of law or fact that constitutes ‘a fundamental defect which inherently results in complete miscarriage of justice.'”

Graziano v. United States, 83 F.3d 587, 589-90 (2d Cir. 1996) (citing United States v. Bokun, 73 F.3d 8, 12 (2d Cir. 1995)).

[N]ot “every asserted error of law can be raised on a § 2255 motion.” See Davis v. United States, 417 U.S. 333, 346 (1974) . . . . The grounds provided in section 2255 for collateral attack on a final judgment in a federal criminal case are narrowly limited, and it has “long been settled law that an error that may justify reversal on direct appeal will not necessarily support a collateral attack on a final judgment.” United States v. Addonizio, 442 U.S. 178, 184 (1979) . . . .”

Napoli v. United States, 32 F.3d 31, 35 (2d Cir. 1994), amended on reh'g on other grounds, 45 F.3d 680 (2d Cir. 1995). Constitutional errors will not be corrected through a writ of habeas corpus unless they have had a “substantial and injurious effect, ” that is, unless they have resulted in “actual prejudice.” Brecht v. Abrahamson, 507 U.S. 619, 623, 637-38 (1993); see also Underwood v. United States, 166 F.3d 84, 87 (2d Cir. 1999) (applying Brecht to § 2255 motions).

         “A § 2255 motion may not relitigate issues that were raised and considered on direct appeal.” United States v. Perez, 129 F.3d 255, 260 (2d Cir. 1997) (declined to review plea withdrawal claim that had already been argued on appeal). This “so-called mandate rule bars re-litigation of issues already decided on direct appeal.” Yick Man Mui v. United States, 614 F.3d 50, 54 (2d Cir. 2010)(citation omitted). “The mandate rule prevents re-litigation in the district court not only of matters expressly decided by the appellate court, but also precludes re-litigation of issues impliedly resolved by the appellate court's mandate.” Yick Man Mui, 614 F.3d at 53.

         “[F]ailure to raise a claim on direct appeal is itself a default of normal appellate procedure, which a defendant can overcome only by showing cause and prejudice.” Campino v. United States, 968 F.2d 187, 190 (2d Cir. 1992). This rule is applied because of concerns about “finality, accuracy and the integrity of prior proceedings, as well as concerns of judicial economy.” Id. “[C]ollateral review of convictions ‘places a heavy burden on scarce judicial resources, may give litigants incentives to withhold claims for manipulative purposes, and may create disincentives to present claims when evidence is fresh.'” Id. (quoting Keeney v. Tamayo Reyes, 504 U.S. 1, 7 (1992)).

         To obtain review of procedurally defaulted claims, the petitioner must show both “cause” for the default of each claim and “prejudice” that resulted from the alleged violation. See Ciak v. United States, 59 F.3d 296, 301, 302 (2d Cir. 1995), abrogated on other grounds by Mickens v. Taylor, 535 U.S. 162, 172 n.3 (2002) (quoting Wainwright v. Sykes, 433 U.S. 72, 87 (1977)). “Where the petitioner--whether a state or federal prisoner--failed properly to raise his claim on direct review, the writ is available only if the petitioner establishes ‘cause' for the waiver and shows ‘actual prejudice from the alleged . . . violation.'” Reed v. Farley, 512 U.S. 339, 354 (1994) (quoting Wainwright, 433 U.S. at 84).

         “‘Cause' under the cause and prejudice test must be something external to the petitioner, something that cannot fairly be attributed to him”. Coleman v. Thompson, 501 U.S. 722, 753 (1991) (emphasis in original). “[T]he existence of cause for a procedural default must ordinarily turn on whether the prisoner can show that some objective factor external to the defense impeded counsel's efforts to comply with the . . . procedural rule.” Id. (quotation marks omitted) (quoting Murray v. Carrier, 477 U.S. 478, 488 (1986)).

         To demonstrate prejudice, a petitioner must convince the court “that ‘there is a reasonable probability' that the result of the trial would have been different” if not for the alleged error. Strickler v. Greene,527 U.S. 263, 289 (1999) (applying the cause-and-prejudice standard to a state procedural default in a § 2254 habeas case). The question is whether, despite the error, “[the petitioner] received a fair trial, understood as a trial resulting in a verdict worthy of ...

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