The opinion of the court was delivered by: Norman A. Mordue, Chief U.S. District Judge
MEMORANDUM-DECISION AND ORDER
On April 29, 2004, a Second Superseding Indictment was returned by a grand jury sitting in the Northern District of New York. See 03-CR-0243, Dkt. No. 315 ("Superceding Indictment"). That instrument alleged that petitioner pro se Leonard Holbdy and others combined, conspired, confederated, and agreed to engage in a pattern of racketeering activity through their membership in a criminal enterprise known as the Boot Camp Gang. Paragraph 11 of that instrument alleged that on or about June 27, 2003, Holbdy assisted another individual who committed the murder of Demetrious Elmore with a .45 caliber handgun.*fn2 The Superceding Indictment further alleged that the defendants agreed to conduct the affairs of that enterprise through a pattern of racketeering activity by engaging in acts of: 1) murder, in violation of New York Penal Law §§ 125.25, 110.05 and 105.17; 2) conspiracy to possess with intent to distribute and distribution of cocaine base (crack) and marijuana; 3) obstruction of justice, in violation of 18 U.S.C. § 1503; and 4) witness tampering, contrary to 18 U.S.C. § 1512(b)(3). See Superceding Indictment at pp. 6-7. Holbdy was specifically referenced in overt acts nos. 43 and 45 of that instrument. Those acts claimed that on or about September 26, 2001, he possessed 3.1 grams of crack cocaine, and that on June 27, 2003, he drove his car so that Christian Williams, a co-defendant in the Superceding Indictment, could kill Elmore, who was a member of a rival gang in the Syracuse, New York area. See Superceding Indictment, Overt Acts Nos. 43 and 45.
On June 7, 2004, following negotiations between Holbdy's counsel and Assistant United States Attorney John Katko ("AUSA Katko"), the parties entered into a plea agreement relating to the charges brought against Holbdy. 03-CR-0243, Dkt. No. 331 ("Plea Agreement"). In that agreement, the parties set forth in detail all the terms of the agreement, including among other things, the maximum sentence to which Holbdy was subject; the potential range of imprisonment that could be imposed on him under the United States Sentencing Guidelines ("Sentencing Guidelines" or "U.S.S.G." ); the factual basis for his guilty plea, and the fact that in the plea agreement, Holbdy was expressly waiving his right to appeal or collaterally attack his conviction and any sentence of imprisonment of 300 months or less. See Plea Agreement. In that agreement, Holbdy admitted the following facts: i) at some point in 1995 through the date of the Superceding Indictment, Holbdy, along with other members of the Boot Camp Gang, combined, conspired, confederated and agreed to engage in a pattern of racketeering activity that included possessing with intent to distribute and distributing cocaine base (crack) and marijuana; ii) Boot Camp Gang members routinely guarded gang territory and resorted to acts of violence to ensure that no rival gang members encroached upon that territory; iii) Holbdy was a member of the Boot Camp Gang who had possessed crack cocaine in connection with his gang activity, including on or about September 26, 2001; iv) as a member of the Boot Camp Gang, he was involved in the June 27, 2003 shooting death of Elmore; v) on that day, Holbdy drove his car so that Christian Williams, a passenger in Holbdy's car and fellow Boot Camp Gang member, could shoot and kill Elmore; and v) Holbdy was responsible, either directly or through the relevant conduct of his co-conspirators, for at least 50 but less than 150 grams of cocaine base (crack). See Plea Agreement at pp. 3-4. In that agreement, Holbdy also admitted that, based upon his conduct that was readily provable by the Government, his admitted involvement in the Elmore murder caused the base offense level for his crime to be 43 under the United States Sentencing Guidelines. See Plea Agreement at ¶ 7(c); see also U.S.S.G. § 2A1.1.*fn3 That Plea Agreement also contained a waiver of his right to appeal and/or collaterally attack his conviction and any sentence of imprisonment of 300 months or less. Plea Agreement at ¶ 11.
At the proceeding over which this Court presided wherein Holbdy formally entered his change of plea, the Court informed him of his rights and the consequences of his plea. See Transcript of Change of Plea of Leonard Holbdy (05-CV-1406, Attachment to Dkt. No. 5) ("Plea Tr.") at pp. 2-4. After Holbdy acknowledged that he understood his rights, id. at p. 4, the Court took his guilty plea and then asked him a number of questions regarding his background and prior drug use. Id. at pp. 7-10. Holbdy then acknowledged that counsel had advised Holbdy of his rights, and declared that he was satisfied with his counsel's representation of him. Id. at 10. The Court then elicited answers from him which established that he had not been threatened into changing his plea, he was not under any duress, and he was entering the plea voluntarily and of his own free will. Id. at 10-11. AUSA Katko then discussed what the Government would have proven if this case had gone to trial, which included proof that Holbdy: i) possessed crack cocaine on September 26, 2001; ii) together with his co-defendants, were criminally responsible for at least 50 grams of crack cocaine and iii) was involved in the June 27, 2003 homicide of Elmore. Id. at 13-14. This Court then asked Holbdy if the prosecutor's statement as to what had occurred was, in fact, what had transpired, to which petitioner responded, "Yes sir." Id. at 15. When the Court asked Holbdy if there was "[a]ny question about that," he responded: "No sir." Id. The Court then requested that AUSA Katko reiterate the stipulations into which Holbdy had entered in the Plea Agreement that related to the penalties to which he was subject. Id. at p. 15. The prosecutor then noted that, pursuant to paragraph seven of the Plea Agreement, Holbdy "stipulate[d] that because of his involvement in the murder [of Elmore], his Base Offense Level [wa]s 43, for (sic) which three points w[ould] be subtracted because of his timely acceptance of responsibility, for a [Total] Offense Level of 40." Id. at pp. 15-16. The Court then accepted his guilty plea. Id. at pp. 21-22.
The Probation Department for the Northern District of New York thereafter prepared a Pretrial Services Report ("PSR") in the related criminal matter. Defense counsel subsequently submitted a sentencing memorandum on November 16, 2004. 03-CR-0243, Dkt. No. 477 ("Sentencing Mem."). In that memorandum, counsel argued various aspects in support of Holbdy's claim that his criminal history category was improperly calculated and that, in any event, his criminal history was overstated by the Probation Department. Specifically, counsel argued that Holbdy's base offense level should be lowered because, according to counsel, Holbdy's participation in the murder of Elmore amounted to no more than second degree murder under the Sentencing Guidelines. See Sentencing Mem. at pp. 2-6. Defense counsel also argued for a downward departure from the recommended criminal history category of level IV. In support of that assertion, counsel noted that the majority of Holbdy's criminal history points arose out of youthful offender adjudications and misdemeanor offenses, which counsel argued "significantly over-represen[ted] the seriousness of [Holbdy's] criminal history" Id. at 8.
At Holbdy's sentencing, trial counsel reiterated his arguments relating to Holbdy's base offense level and criminal history category. See Transcript of Sentencing of Leonard Holbdy (6/7/04) ("Sentencing Tr.") at pp. 3-4. In rejecting Holbdy's argument regarding the Court's treatment of the murder of Elmore for sentencing purposes, this Court noted that Holbdy "absolutely knew before" the incident that Williams intended to kill Elmore, and that Holbdy had "set the stage" for the murder by driving the car into position for Williams to shoot Elmore. Id. at 8. The Court also rejected counsel's arguments relating to Holbdy's criminal history score, concluding that the PSR did not overstate the likelihood that he would commit another crime. Id. at p. 9. After granting the Government's downward departure motion due to Holbdy's acceptance of responsibility, this Court imposed a sentence of 300 months on him. Id. at p. 15. This Court then reiterated the fact that, under the terms of the Plea Agreement, Holbdy could not appeal his conviction or sentence. Id. at pp. 17-18.
Holbdy did not file any appeal of his conviction or sentence. See Motion to Vacate, Set Aside or Correct Sentence (05-CV-1406, Dkt. No. 1) ("Motion to Vacate") at ¶ 8. However, on November 10, 2005, he filed his Motion to Vacate in which he claims that his conviction and sentence should be set aside because he received the ineffective assistance of counsel. See Motion to Vacate; see also Memorandum of Law in Support of Motion to Vacate (05-CV-1406, Dkt. No. 2) ("Supporting Mem."). Respondent has filed a memorandum of law in opposition to Holbdy's application, 05-CV-1406, Dkt. No. 5, to which Holbdy filed a reply memorandum of law in further support of his Motion to Vacate. 05-CV-1406, Dkt. No. 6. By application signed by Holbdy on June 10, 2008, he seeks permission to amend and/or supplement his Motion to Vacate and to assert herein several new grounds for relief. See 05-CV-1406, Dkt. No. 8.
The Sixth Amendment to the United States Constitution provides that "[i]n all criminal prosecutions, the accused shall enjoy the right ... to have the Assistance of Counsel for his defence." This right to counsel has long been recognized as one that entitles a defendant to the right to the effective assistance of counsel. See McMann v. Richardson, 397 U.S. 759, 771 n.14 (1970). Under the now familiar two-part test enunciated in Strickland v. Washington, 466 U.S. 668 (1984), an individual who claims he received the ineffective assistance of counsel must demonstrate that the representation: 1) "fell below an objective standard of reasonableness," Strickland, 466 U.S. at 688; and 2) prejudiced the petitioner. Id. at 694. See Campusano v. United States, 442 F.3d 770, 773 (2d Cir. 2006); United States v. Champion, 234 F.3d 106, 109 (2d Cir. 2000).
In evaluating the first prong of the test, this Court notes that "counsel 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. In order to establish the second prong of Strickland in the context of a guilty plea, a petitioner must demonstrate that there is a reasonable probability that, but for counsel's claimed errors, he would not have pleaded guilty and would have instead insisted on going to trial. Hill v. Lockhart, 474 U.S. 52, 59 (1985). Moreover, the petitioner bears the burden of proving that he did not receive effective assistance of counsel. Kimmelman v. Morrison, 477 U.S. 365, 381 (1986); see also Williams v. United States, 481 F.2d 339, 346 (2d Cir. 1973); Parsons v. United States, 919 F.Supp. 86, 88-89 (N.D.N.Y. 1996) (Munson, J.) (citation omitted).
B. Review of Holbdy's Claims*fn4
1. Impact of Elmore Murder on Holbdy's Sentence
Holbdy initially claims that in calculating his base offense level for sentencing purposes, the Probation Department "illegal[ly]" based that calculation in part on his claimed role in the Elmore murder, which in turn had a "tremendous" and adverse effect on the prison term to which he was ultimately sentenced. See Supporting Mem. at 3-4. Petitioner asserts that trial counsel's failure to inform Holbdy that the Probation Department might refer to that crime in preparing the PSR "clearly ... violated [Holbdy's] Sixth Amendment Right to Effective Assistance," Supporting Mem. at p. 3, and that Holbdy "would have NEVER waive[d] his Appeal ...