MANHATTAN (CN) - Bernard Madoff's massive Ponzi scheme has nothing to do with the civil rights movement, and the Second Circuit must consider now whether a prosecutor's conflation of the two issues helps boost five of the fraudster's former employees out of prison.
Daniel Bonventre, Annette Bongiorno, JoAnn Crupi, Jerome O'Hara and George Perez took their appeal to the Second Circuit today nearly two years to the day that a jury convicted the former Madoff Securities employees after a five-month trial.
While O'Hara and Perez, the firm's ex-computer programmers, are approaching the end of their 30-month sentences, Bonventre, the firm's former director of operations, still has 80 percent of his 10-year term to go.
Investment advisers Bongiorno and Crupi are not quite halfway through six-year sentences.
The "Madoff Five," as they were christened at trial, insist that their boss kept them in the dark about the colossal fraud he had perpetrated, but jurors found that the employees either knew or should have known what was happening.
With all five having worked for Madoff for decades, U.S. District Judge Laura Taylor Swain agreed that "considerable evidence" supported the conclusion.
Their lawyers each contested various aspects of the evidence at a Second Circuit hearing Tuesday, alternately pleading their client's ignorance or charging that prosecutors withheld evidence.
A common refrain in each argument, however, challenged the rebuttal summations of former Assistant U.S. Attorney Randall Jackson.
Though now in private practice, the black prosecutor's fiery rhetoric has put him in hot water with appeals court before.
Back in 2014, Jackson invoked legendary civil rights leaders and jurists Constance Baker Motley and Thurgood Marshall to urge that jurors have the "courage" to imprison the Madoff Five.
Judge Swain had chided the analogy after the trial as "at best, ambiguous and at worst, unfathomable."
But Bonventre's attorney Andrew Frisch told the Second Circuit today that Jackson's "visceral appeal to emotion" swayed the largely black jury to overlook what he described as the government's shaky case.
No one on the three-judge panel stood ready to credit Jackson for an apt metaphor, but Circuit Judge Reena Raggi seemed skeptical that the remark carried racial undertones.
"It just seems like a foolish argument that doesn't advance it at all," Raggi said.
Turning to private practice has been a trend for all of the original Madoff Five prosecutors, however, leaving the government's appeals team struggling today to explain Jackson's reference.
Assistant U.S. Attorney Aimee Hector nevertheless appeared reluctant to concede any mistake by the trial prosecutors.
"In hindsight, may we have made different choices?" she said. "Perhaps."
Hector insisted, however, that Jackson's comparison was an appropriate counterargument to a historical analogy the defense made to John Adams, who won the acquittals of British soldiers on trial over the Boston Massacre.
The case made Adams iconic for the principle of ensuring fair-trial rights for even the most despised defendants.
Likewise, Motley and Marshall courageously risked their lives as civil rights lawyers to pursue justice in the Jim Crow South, before later becoming boundary-breaking judges. Motley became the first black, female federal judge. Marshall, after whom the Second Circuit's courthouse is named, became the first black Supreme Court justice.
Referring to this historical context, Hector said: "I submit, it was responsive."
"It was responsive to a specific point made by the defense," she said.
Undercutting this argument, however, the government here is defending the arguments by prosecutors gunning for a conviction, while Motley and Marshall were defense attorneys, like Adams, who fought to defend unpopular clients.
Each judge hearing the case today appeared to agree that Jackson's point, however it was intended, missed the mark.
Jackson also faced criticism for repeatedly mocking defense arguments as "ridiculous and absurd."
Quoting Judge Swain's finding that this ridicule was "ill-conceived and unworthy of your office," Raggi called this remark an "extraordinary criticism by a very balanced judge."
"We have an experienced trial judge saying that this argument was unworthy of your office," she emphasized.
Circuit Judge John Walker said that the timing of Jackson's remarks made them more problematic.
"This is the last thing the jury heard before deliberations," he said. "Rebuttals have to be handled in a responsible way, and I'm not sure it was."
They appeared convinced this afternoon that Jackson had crossed a line, but Raggi questioned if the comments were egregious enough to grant the defendants relief.
"If the government prevails, it's because Judge Swain mitigated this harm with her instructions, not because they were permissible," she warned.
Bonventre's lawyer told the judges not to give the prosecution a pass.
"Admonishing prosecutors for arguments that shouldn't be made could become an acceptable cost of doing business," Frisch said.
Ironically, while appellate lawyers debated the meaning of his remarks, Jackson had been in a different courtroom of the same building, where he is currently representing drivers suing General Motors for installing defective ignition-switches in their cars.
The last time Jackson's remarks as a prosecutor brought an appellate challenge was in the case of so-called "cannibal cop" Gilberto Valle, who was convicted of plotting to kidnap, cook, rape and eat women.
Valle, who was exonerated on appeal, had always insisted that he was being prosecuted for "thought crimes" that were nothing more than sexual fantasies.
In a pattern of backfiring analogies, Jackson compared this defense at the time to an airplane hijacker announcing that he was joking, a comment that defense attorneys found inflammatory in a courtroom a short walk away from the World Trade Center.
On appeal, the Second Circuit agreed that the comment was inappropriate, but they found in Valle's favor on First Amendment grounds.