The opinion of the court was delivered by: Amy J. St. Eve, District Court Judge:
MEMORANDUM OPINION AND ORDER
Before the Court is Petitioner Abdelhaleem Ashqar's motion to vacate, set aside, or correct his sentence pursuant to 28 U.S.C. § 2255. For the following reasons, the Court denies Ashqar's Section 2255 motion. Further, the Court declines to certify any issues for appeal pursuant to 28 U.S.C. § 2253(c)(2).
On August 19, 2004, a grand jury returned a second superseding indictment charging Ashqar with criminal contempt in violation of 18 U.S.C. § 401(3), obstruction of justice in violation of 18 U.S.C. § 1503, and a racketeering conspiracy in violation of 18 U.S.C. § 1962(d). In 1989, Ashqar -- a Palestinian national -- entered the United States as a Ph.D. student in business administration at the University of Mississippi, where he graduated in 1997. At trial, the government presented evidence of Ashqar's involvement in Hamas, a designated foreign terrorist organization, including documents the FBI found in a search of Ashqar's Mississippi residence in 1993, wiretap intercepts, and fax communications.
Ashqar's obstruction of justice and criminal contempt charges stem from his refusal to testify before a grand jury that was investigating the funding of Hamas. More specifically, in June 2003, a federal grand jury sitting in the United States District Court for the Northern District of Illinois subpoenaed Ashqar to testify as part of an investigation into Hamas and its possible violations of United States law. On June 25, 2003, Ashqar appeared before the grand jury, and, after being sworn in, the government informed him about the nature of the investigation, his rights under the Fifth and Sixth Amendments, and of the potential penalties for obstruction of justice and perjury. The government then asked Ashqar a series of questions in reference to the grand jury investigation, but Ashqar refused to answer questions relating to Hamas. Instead, Ashqar read from a prepared statement giving his reasons for refusing to testify, including that he believed that answering the questions would violate his religious, political, and personal beliefs; the Israeli government would use his statements to persecute and torture him; and that his answers would be used against his friends and relatives, among other reasons. Ashqar further stated to the grand jury: "I will never give evidence or cooperate in any way with the grand jury or any other, no matter what the consequences to me."
After Ashqar refused to answer the government's questions, the grand jury temporarily adjourned. Ashqar and his attorney then appeared before Judge Charles Kocoras, who was Chief Judge of the Northern District of Illinois at that time. Upon the government's application, Chief Judge Kocoras granted Ashqar immunity for any truthful statements he made before the grand jury and ordered Ashqar to answer the questions. The government also offered to place Ashqar and his family under the United States Federal Witness Protection Program. Nonetheless, Ashqar continued to refuse to answer any questions. The government then warned Ashqar that it could prosecute him for criminal contempt and obstruction of justice. Ashqar responded by re- reading his prepared statement. Subsequently, Chief Judge Kocoras held Ashqar in civil contempt.
The August 19, 2004 superseding indictment not only charged Ashqar with criminal contempt and obstruction of justice, but also with a racketeering conspiracy with co-defendants Mousa Abu Marzook ("Marzook") and Muhammad Salah ("Salah"). Ashqar's and Salah's trial began on October 12, 2006 and concluded on February 1, 2007.*fn1 On February 1, 2007, the jury convicted Ashqar of the criminal contempt and obstruction of justice charges, but acquitted him of the racketeering conspiracy charge. On November 21, 2007, the Court sentenced Ashqar to 135 months imprisonment for the criminal contempt conviction and a concurrent term of 120 months imprisonment for the obstruction of justice conviction. Ashqar appealed and the Seventh Circuit affirmed his conviction and sentenced on October 2, 2009. See United States v. Ashqar, 582 F.3d 819 (7th Cir. 2009). The United States Supreme Court denied Ashqar's petition for a writ of certiorari on March 1, 2010 and Ashqar filed the present Section 2255 motion on January 26, 2011.
"[R]elief under § 2255 is an extraordinary remedy because it asks the district court essentially to reopen the criminal process to a person who already has had an opportunity for full process." Almonacid v. United States, 476 F.3d 518, 521 (7th Cir. 2007). Under Section 2255, relief "is available only when the 'sentence was imposed in violation of the Constitution or laws of the United States,' the court lacked jurisdiction, the sentence was greater than the maximum authorized by law, or it is otherwise subject to collateral attack." Torzala v. United States, 545 F.3d 517, 521 (7th Cir. 2008) (quoting 28 U.S.C. § 2255). A Section 2255 motion is not a substitute for a direct criminal appeal nor is it a means by which a defendant may appeal the same claims a second time. See Varela v. United States, 481 F.3d 932, 935 (7th Cir. 2007) (a Section 2255 motion is "neither a recapitulation of nor a substitute for direct appeal"). As such, if a Section 2255 petitioner does not raise a claim on direct appeal, that claim is barred from the Court's collateral review unless the petitioner can demonstrate cause for the procedural default and actual prejudice from the failure to appeal. See Sandoval v. United States, 574 F.3d 847, 850-51 (7th Cir. 2009); Torzala, 545 F.3d at 522. Because ineffective assistance of counsel claims usually involve evidence outside of the trial record, such claims may be brought for the first time in a Section 2255 motion. See Massaro v. United States, 538 U.S. 500, 504, 123 S.Ct. 1690, 155 L.Ed.2d 714 (2003).
In his Section 2255 motion, Ashqar, who is represented by counsel, argues that his defense counsel, William Moffitt, was suffering from kidney failure during the trial and appeal of his case and that had he known about Moffitt's kidney disease and the attendant dialysis treatment, he would have retained another lawyer to represent him.*fn2 Ashqar admits, however, that such a serious medical condition, standing alone, does not establish ineffective assistance of counsel, but instead provides context to his claims. See Sanders v. United States, 288 Fed.Appx. 283, 287, 2008 WL 2821588, at *3 (7th Cir. 2008) ("Outside influences such as serious illness or use of medication might explain a deficiency, but they do not constitute deficiencies by themselves.") (emphasis in original). Ashqar brings both ineffective assistance of trial and appellate counsel claims based on Moffitt's representation, although other attorneys represented Ashqar during his criminal proceedings, including Keith Spielfogel, who was present throughout Ashqar's three-month trial and filed numerous motions and legal memoranda on behalf of Ashqar.
I. Ineffective Assistance of Trial Counsel
Ashqar first argues that his trial counsel failed to provide effective assistance of counsel under the Sixth Amendment. To establish constitutionally ineffective assistance of counsel, Ashqar must establish that (1) his attorney's performance "fell below an objective standard of reasonableness," and (2) "but for counsel's unprofessional errors the result of the proceeding would have been different" meaning "a probability sufficient to undermine confidence in the outcome." Strickland v. Washington, 466 U.S. 668, 688, 694, 104 S.Ct. 2052, 80 L.Ed.2d 674 (1984). The Court's "review of the attorney's performance is 'highly deferential' and reflects 'a strong presumption that counsel's conduct falls within the wide range of reasonable professional assistance; that is, the defendant must overcome the presumption that, under the circumstances, the challenged action might be considered sound trial strategy.'" Koons v. United States, 639 F.3d 348, 351 (7th Cir. 2011) (citation omitted). Courts "assess counsel's work as a whole, and 'it is the overall deficient performance, rather than a specific failing, that constitutes the ground of relief.'" See Brown v. Finnan, 598 F.3d 416, 422 (7th Cir. 2010) (citation omitted). Meanwhile, if Ashqar fails to make a proper showing under one of the Strickland prongs, the Court need not consider the other. See id. at 697 ("In particular, a ...