Once prominent Chicago banker waiting for word on his destiny

CHICAGO (WLS) -- Stephen Calk is asking a federal appeals court to toss out his conviction in a bank bribery scheme that involved Donald Trump's one-time campaign chairman.

A sharp color photo may have been the closest that Stephen Calk and Donald Trump actually ever came; even though history will remember them standing together as the Quid and the Quo of a campaign-era deal that never was.

Calk is the founder of the Federal Savings Bank in Chicago. He wanted a top job in the Trump administration, suggesting perhaps Secretary of the Army, and he approved 16-million in bank loans to Trump's campaign director.

Trump's 2016 campaign chairman was Paul Manafort. The lanky political prince who received millions in loans from Chicago's Federal Savings Bank was courtesy of Calk, according to federal prosecutors, They convinced a jury that the Chicago banker okayed those loans with an expectation he would land a top Trump job

Even though the Quid and the Quo never were consummated, the case ended up consuming Calk in court.

In 2022, he was sentenced to a year and a day in prison. But this week, Calk was back in the halls of justice, in the Second Circuit Court of Appeals. What was scheduled for a 20- minute oral argument ended up being an hour-long.

"It tells us that the appellate court sees itself as grappling with maybe a tough issue and these are issues involving public corruption," said former Chicago federal prosecutor and ABC 7's chief legal analyst Gil Soffer.

Calk's attorney, Alexandra Shapiro, told justices this was an unprecedented use of bank bribery statutes.

Justice Guido Calabresi repeatedly raised the uniqueness of the case against Calk.

In court, Judge Guido Calabresi of the 2nd Circuit Court of Appeals said, "What we're asking is what was in Mr. Calk's mind when he was doing this? And whether that is evidence of the value of this to him?"

"This is a case where the defendant made a loan or participated in making a loan. That's the business of a bank," said Soffer. "It's a case where what he got in return wasn't a bag of cash. It was a potential job. That's a little different from the standard bank fraud case."

The government contends Calk bent over backwards to approve irregular and risky loans aimed at landing a cabinet job or ambassadorship. Calk's attorney told appellate judges the Chicago banker's loans were standard and that he walked away with no appointment of any kind. The question is whether that appeals court will reverse a jury verdict, send it back for retrial or send Calk to his sentence.