Defense attorneys and prosecutors in the bombshell corruption case against Chicago’s longest-serving alderman politely duked it out in federal court Tuesday in arguments that spanned whether a jury should be able to hear federally wiretapped phone conversations to what constitutes a bribe in Chicago.

In 2019, Ald. Ed Burke, 14th Ward, was slapped with 14 counts of racketeering, bribery and attempted extortion for allegedly using his clout in City Hall to steer business to his private law practice, Klafter & Burke, and forcing developers to appeal their property taxes using his firm. The stunning indictment came just months after federal authorities raided Burke’s City Hall and ward offices.

Tuesday’s hearing revolved around hundreds of pages of pre-trial motions filed by Burke’s attorneys and the U.S. government. Those filings, along with the pandemic, have delayed a potential jury trial for the 78-year-old Burke, who was not present at Tuesday’s hearing.

U.S. District Judge Robert Dow on Tuesday said he needed to put time limits on the two-hour hearing because “the number of issues is pretty insurmountable,” and has called the amount of pre-trial work “unprecedented.”

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Federal authorities accuse Burke of attempting to shake down a Burger King, capitalize on a massive renovation of Chicago’s Old Post Office and broker a deal with his co-defendant, businessman Charles Cui, to trade property tax business for help with a project in Portage Park.

Among the motions filed, Burke’s lawyers argued Tuesday against the use of evidence presumably at the heart of the government’s case – wiretapped phone calls and conversations with former Ald. Danny Solis. Through wiretaps, federal agents recorded close to 10,000 phone calls in the case.

Solis, who until 2019 represented the 25th Ward and chaired the powerful zoning committee, wore a wire for the feds after he was confronted with evidence of his own wrongdoing.

Burke’s defense team on Tuesday argued against the validity of that wiretap altogether, saying the federal government relied too heavily on Chicago’s supposed reputation for corruption, and Solis’ own wrongdoing, in its application for Solis to wear a wire around Burke in the first place.

The federal government went to the judge who signed off on that wiretap nine times, Burke’s attorney Andrew DeVooght said, feeding the judge a “steady diet of literally hundreds of pages” of Solis’ infractions in an effort to justify the wiretap. The intention was to imply that Solis was at it again, but “this time with Ald. Burke,” DeVooght said.

They argued that a “well-coached, well-prepared Ald. Solis” – whose prosecution was deferred as part of the agreement to record Burke, they said – repeatedly tried to prompt Burke into agreeing to or admitting wrongdoing, but that Burke never took action or implied that he would.

But prosecutors argued that Burke was not oblivious, referencing one conversation in which he allegedly tells Solis to “get me some business from these guys.” That appeared to refer to a developer who was seeking council approval for a project that, as zoning chair, Solis could influence.

Lead prosecutor Amarjeet Singh Bhachu added that through these conversations, it’s “logical and fair” to believe that Burke was aware he was using his and Solis’ positions in council as leverage to steer business to his firm.

Also center stage at Tuesday’s hearing was an argument over whether Burke’s dealings with his co-defendant Charles Cui and other actions were really bribes at all, or if two bribery-related charges should instead be dismissed, as the defense argues.

Cui is accused of hiring Burke’s law firm to appeal his property taxes in exchange for help getting a sign permit for a business venture in Chicago’s Portage Park neighborhood. Prosecutors argued there was “corrupt intent” behind that exchange.

“Work procured through a bribe is not legitimate,” prosecutor Julia Schwartz said, adding that the work “wasn’t necessary” because Cui already had a property tax firm in his rolodex – “a firm he jettisoned because he needed Burke’s favor,” she said.

In its allotted five-minute rebuttal, the defense team stated Cui had a property tax firm for a prior year, but needed a new one.

At the beginning and end of Tuesday’s hearing, Dow warned of the amount of work still left to do ahead of any potential trial date, saying it’s a “big case that requires a big opinion” and that Tuesday’s hearing – although a significant step forward – doesn’t change that.

“I don’t think you agreed on too much,” he said facetiously to the defense and prosecution. “So it’s not like I don’t still have a ton of work to do.”

Burke was not required to appear at Tuesday’s hearing and has been largely mum on the case against him. In 2019, after an initial criminal complaint was filed, Burke said he’s “done nothing wrong. And anything that Alderman Solis recorded, if he did, isn’t going to make any difference.”

Although Burke is still a sitting alderman, he has largely lost his power of influence over the council. Burke stepped down from his role leading the council’s Finance Committee and Chicago Mayor Lori Lightfoot has repeatedly called for him to resign his seat entirely amid the sprawling corruption probe.

Burke is not the only sitting Chicago alderman with a case up in federal court just this week. The long-awaited hearing comes just a day after the start of the unrelated federal trial for Ald. Patrick Daley Thompson, grandson and nephew of the city’s two longest-serving mayors.

Thompson was indicted last April on charges of tax fraud related to loans he received from a disgraced and now-shuttered Bridgeport bank. Thompson has pleaded not guilty and maintained that he is innocent.

Regardless of the outcome of their trials, both aldermen have or will face challenges ahead in maintaining their positions in the council.

That’s in part due to the drawn out and combative redistricting process underway at City Hall – where aldermen remap the city’s voting districts to ensure all 50 wards are equal in size amid a changing population.

In a map proposed by the council’s Latino caucus, Burke’s ward would change significantly by bolstering the ward’s Latino population and excluding some blocks that have been a stronghold for Burke, potentially endangering his chances for reelection.

Under both dueling proposals, Thompson’s ward would also face drastic changes, as both sides – the council’s Latino and Black caucuses – agree that his 11th ward will be the one to become the city’s first Asian-majority ward. Thompson opposes that change.

Mariah Woelfel covers Chicago city government at WBEZ. You can follow her @MariahWoelfel.