Veteran criminal defense lawyer Edward Genson has been called "one of the best criminal defense lawyers–if not the best" in Chicago; a "master of cross-examination" who is "wily and pugnacious;" as well as a "barracuda" who is the go-to-guy for clients facing "unwinnable" cases.

That, apparently, wasn’t good enough for Conrad Black.

On Tuesday a federal judge in Chicago rejected Black’s argument that his 2007 fraud and obstruction of justice convictions were invalid because he was unconstitutionally deprived of his preferred defense attorneys, Brendan Sullivan and Gregory Craig, and forced to use Genson instead.

Black’s motion to vacate his conviction, filed by Baker & Hostetler, asserted that the government unlawfully seized $9 million in proceeds from the sale of Black’s Manhattan apartment in 2005, rendering him unable to hire William & Connolly’s Sullivan and Craig. (Craig is now at Skadden, Arps, Slate, Meagher & Flom.) Instead, Black hired Genson of Genson & Gillespie and Edward Greenspan of Greenspan Partners in Toronto. Black was convicted on three counts of mail fraud and one count of obstruction in 2007, but the U.S. Court of Appeals for the Seventh Circuit reversed two of those convictions after the U.S. Supreme Court sharply limited the scope of the "honest services" laws. Black served almost four years and was released from prison last May.

In a 16-page opinion, U.S. District Judge Amy St. Eve, who presided over the Black trial, held that Black waited too long to raise this argument. "[T]he docket contains over 800 entries before the jury returned its verdict," she wrote. "During the course of pretrial proceedings and the trial, [Black] never informed the court that he was not represented by his counsel of choice." Similarly, St. Eve ruled that Black should have objected earlier to the seizure of property.

In a long footnote, the judge defended Genson as "extremely talented" and pointed out that Black’s legal team included plenty of other heavy hitters, including appellate lawyers Andrew Frey of Mayer Brown and Miguel Estrada of Gibson, Dunn & Crutcher. "The Court notes that Petitioner’s trial and appellate counsel were some of the most talented and well-respected attorneys in their field," St. Eve wrote.

We reached out to Genson and Greenspan, and did not hear back.

Black’s attorney, Wiliam Kane of Baker & Hostetler, did not respond to our request for comment. In a statement given to Bloomberg News, Black conceded that he "never thought there was much chance that Judge St. Eve would rule in [his] favor" and decried the prosecution as a "fraud and a disgrace." "I have left the country," Black said in his email. "The vagaries of the American justice system are not my problem now."