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Whittingham v. United States

United States District Court, S.D. New York

May 22, 2017

TREVOR WHITTINGHAM, Petitioner,
v.
UNITED STATES OF AMERICA, Respondent. UNITED STATES OF AMERICA
v.
TREVOR WHITTINGHAM, Defendant.

          OPINION & ORDER

          RICHARD J. SULLIVAN, District Judge

         Trevor Whittingham (“Petitioner”), proceeding pro se, brings: (1) a petition for the issuance of a writ of habeas corpus pursuant to 28 U.S.C. § 2255 (Doc. No. 30 (the “Petition” or “Pet.”), and (2) a motion for early termination of supervised release (Doc. No. 34). For the reasons set forth below, the Court denies both the Petition and the motion for early termination.

         I. Background

         From 2005 to 2009, Petitioner owned and operated parking garage businesses called “EZ Going Park Here” and “We Have Cars II” in New York City, which employed approximately a dozen people. (Doc. No. 16 (“Plea Tr.”) at 36:13-17.)[1] In that capacity, Petitioner was responsible for signing and filing his companies' quarterly tax returns with the Internal Revenue Service (“IRS”) and for paying federal and state payroll taxes. (Id. at 36:25-37:2.) Over that period, Petitioner caused the entities under his control to deduct and collect approximately $251, 265 in payroll taxes from his employees' wages that he failed to pay to the IRS. Instead, Petitioner used the funds for personal expenses such as vacations and automobiles, including a Ferrari sports car. (Doc. No. 26; see also Plea Tr. 39:8-17.)

         On December 20, 2012, a grand jury returned an indictment charging Petitioner with thirteen counts of willful failure to collect, account for, and pay over to the IRS his employees' payroll taxes in violation of 26 U.S.C. § 7202. (Doc. No. 2.) Over the course of his prosecution, Petitioner was represented by three different attorneys: (1) Glenn Ripa, who appeared on his behalf for the limited purposes of representing him at the arraignment on January 3, 2013; (2) Robert Walters, who appeared on Petitioner's behalf on January 22, 2013 and withdrew on May 10, 2013 (Doc. No. 7); and (3) Richard Anthony Portale, who first appeared for Petitioner on April 26, 2013 and continued to represent him for the remainder of the criminal case (Doc. No. 12).

         On July 8, 2013, Petitioner pleaded guilty pursuant to a plea agreement to one count of willful failure to pay over payroll taxes. (Plea Tr. 40:8-20.) At the change-of-plea hearing, Petitioner, while under oath, acknowledged that he had collected payroll tax contributions from his employees, which he knowingly failed to pay over to the IRS and instead pocketed. (Id. at 36:9-37:14.) Following Petitioner's allocution, the government indicated that, had the case gone to trial, it would have presented substantial inculpatory evidence, including: (1) testimony from current and former employees of EZ Going Park Here and We Have Cars II indicating that Petitioner was the person who made hiring decisions and paid them; (2) bank records showing that Petitioner had exclusive control over the entities' finances; (3) testimony from IRS employees that Petitioner did not pay certain payroll taxes he collected on his employees' behalf, notwithstanding the fact that he also submitted documentation to the IRS representing that such payroll taxes had been paid; (4) testimony from Petitioner's accountant that he had informed Petitioner of his obligation to submit payroll taxes to the government on his employees' behalf and that Petitioner had failed to follow this advice; and (5) records of Petitioner's spending to show that he used funds that were meant to be paid over to the IRS on vacations and automobiles for himself. (Plea Tr. 38:19-39:17.) Under the plea agreement, Petitioner reserved the right to argue that he was responsible for a total tax loss of greater than $80, 000 but less than $200, 000, while the government asserted that Petitioner was responsible for a total tax loss of greater than $200, 000 but less than $400, 000. (Doc. No. 25-1 at 3.) On the government's motion, the Court eventually dismissed the twelve remaining counts. (Doc. No. 27 at 1.)

         At Petitioner's sentencing hearing on May 12, 2014, Petitioner conceded that he was responsible for losses of greater than $200, 000 but less than $400, 000, resulting in a base offense level of 18 pursuant to Sections 2T1.6 and 2T4.1 of the United States Sentencing Guidelines (the “Guidelines”); the Court further found that Petitioner was entitled to a three-level reduction for acceptance of responsibility pursuant to Section 3E1.1 in light of his guilty plea, which resulted in a Guidelines range of 18 to 24 months imprisonment. (Doc. No. 28 (“Sent. Tr.”) 3:11-21, 7:2- 23.) Even so, in light of Petitioner's low likelihood of recidivism, his advanced age, and his many contributions to the community, the Court concluded that a below-Guidelines sentence of one year and one day was sufficient but not greater than necessary to meet the objectives of sentencing set forth under 18 U.S.C. § 3553(a). (Id. at 7:2-23, 29:5-16.) The Court also ordered Petitioner to pay restitution in the amount of $251, 265, which represented the amount Petitioner had accumulated in unpaid tax liabilities plus penalties and interest. (Doc. No. 27 at 5; Doc. No. 25-1 at 16.) Petitioner never filed a direct appeal of his sentence.

         On October 1, 2014, while incarcerated, Petitioner filed the instant Petition pro se. In it, Petitioner claims that his various attorneys were ineffective for “inducing Petitioner int[o] a guilty plea” that he did not enter knowingly and voluntarily. (Pet. 3, 7.) In addition, Petitioner faults his lawyers for not moving to compel additional discovery under Rule 16 of the Federal Rules of Criminal Procedure and for failing to sufficiently investigate his case before his guilty plea. (Id. at 3.) Petitioner also asserts that Mr. Portale was constitutionally ineffective for “failing to challenge the loss amount” range of $200, 000 to $400, 000 at sentencing and for neglecting to discuss the presentence investigation report (“PSR”) prepared by the United States Probation Office with him in advance of sentencing. (Id. at 5-6, 10.)

         On February 2, 2017, Petitioner, who is currently serving a term of supervised release that expires on May 20, 2018, brought a motion seeking early termination of supervision. (Doc. No. 34.) In his motion, Petitioner asserts that he is entitled to early termination because of his “excellent behavior, ” his full compliance with the conditions of supervision, and his desire to travel to visit family in Jamaica. (Id.) The Court will consider the Petition and the motion for early termination in turn.[2]

         II. Ineffective Assistance of Counsel

         A. Legal Standard

         Section 2255 enables a prisoner who was sentenced by a federal court to petition that court to vacate, set aside, or correct the sentence on the ground that “the sentence was imposed in violation of the Constitution or laws of the United States . . . or is otherwise subject to collateral attack.” 28 U.S.C. § 2255(a). Relief under Section 2255 is generally available “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 a complete miscarriage of justice.'” United States v. Bokun, 73 F.3d 8, 12 (2d Cir. 1995) (quoting Hill v. United States, 368 U.S. 424, 428 (1962)). “Because collateral challenges are in ‘tension with society's strong interest in the finality of criminal convictions, the courts have established rules that make it more difficult for a defendant to upset a conviction by collateral, as opposed to direct, attack.'” Yick Man Mui v. United States, 614 F.3d 50, 53 (2d Cir. 2010) (citation omitted). A claim of ineffective assistance of counsel, however, is one permissible basis for bringing a Section 2255 petition.

         The Sixth Amendment to the United States Constitution guarantees a criminal defendant's right to the assistance of counsel. When challenging the effectiveness of counsel's assistance, a party must demonstrate that (1) counsel's representation “fell below an objective standard of reasonableness” measured against “prevailing professional norms, ” and (2) this “deficient performance prejudiced the defense” in the sense that “there is a reasonable probability that, but for counsel's unprofessional errors, the result of the proceeding would have been different.” Strickland v. Washington, 466 U.S. 668, 687-88, 694 (1984). A court must reject a petitioner's ineffective assistance of counsel claim if it fails to meet either prong. Gonzalez v. United States, 722 F.3d 118, 130 (2d Cir. 2013).

         With respect to Strickland's first prong, a court “must judge [counsel's] conduct on the basis of the facts of the particular case, ‘viewed as of the time of counsel's conduct, ' and may not use hindsight to second-guess his strategy choices.” Mayo v. Henderson, 13 F.3d 528, 533 (2d Cir. 1994) (quoting Strickland, 466 U.S. at 690). The Court starts from the strong presumption that counsel's conduct fell “within the wide range of reasonable professional assistance.” Strickland, 466 U.S. at 689. “Actions and/or omissions taken by counsel for strategic purposes generally do not constitute ineffective assistance of counsel.” Gibbons v. Savage, 555 F.3d 112, 122 (2d Cir. 2009) (citing Strickland, 466 U.S. at 690-91). Because there are many different ways to provide effective assistance in any given case, and “[e]ven the best criminal defense attorneys would ...


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