Former Illinois House Speaker Michael J. Madigan has about two months left until he’s due in prison, but he’s fought to stay free while he appeals his historic corruption conviction.
It’s not going well, and the once-powerful Southwest Side Democrat shouldn’t get his hopes up, according to legal experts contacted by the Chicago Sun-Times. One said “the odds are stacked” against him. Another said, “It almost never happens.”
“It’s a difficult standard to meet,” defense attorney Michael Leonard said. “It’s really got to jump off the page to the court.”
In fact, U.S. District Judge John Blakey wound up denying Madigan’s initial request for freedom late Friday. The longtime politician is not out of options, though.
Madigan faces 7 ½ years in prison after being convicted in February of bribery conspiracy, wire fraud and other crimes. Blakey ordered him to report to the Federal Bureau of Prisons on Oct. 13.
The conviction revolved around two schemes. In one, ComEd paid five Madigan allies $1.3 million over eight years so that Madigan would look more favorably at the utility’s legislation. The other involved a deal to have then-Chicago Ald. Danny Solis installed on a state board in exchange for Solis’ help landing private business for Madigan’s tax appeal law firm.
Madigan’s attorneys filed their motion for release pending appeal with Blakey on July 14. Now that Blakey has denied it, Madigan could also turn to the 7th U.S. Circuit Court of Appeals, which oversees courts in Illinois, Indiana and Wisconsin.
An attorney for Madigan could not immediately be reached after Blakey’s ruling Friday.
Defense attorney Chris Gair said the granting of such a motion “almost never happens.”
“It’s an incredibly uphill battle for anyone to get bond pending appeal in the 7th Circuit, or really almost anywhere in the federal system,” he said. “And it’s a shame.”
Even before Blakey ruled, Leonard predicted that Madigan’s best hope rested with the 7th Circuit judges. Blakey presided over Madigan’s four-month trial and “was confident” in rejecting Madigan’s request for a new trial or acquittal after the verdict.
“It’d be extremely unlikely for Judge Blakey to believe that he was wrong,” Leonard said before the ruling.
The law requires Madigan to convince a judge that his appeal raises a substantial question of law or fact likely to result in reversal or a new trial, a sentence of no prison time, or so little prison time that it could be served before his appeal is complete.
Madigan’s appeal could take months — or even years — to play out. His lawyers say it will require the 7th Circuit to “assess important, complex, and undecided legal issues” which “collectively affect every count of conviction.”
They’ve pointed to the “considerable ink” spilled in the last few years over the definition of the word “corruptly,” which appears in a bribery statute used to convict him. U.S. Supreme Court justices debated the meaning of the word at oral argument in April 2024.
They left its definition unclear in a ruling that followed, though.
Madigan’s legal team also pointed to a “stream of benefits” theory used by prosecutors to secure Madigan’s conviction. The defense attorneys say it meant jurors did not have to connect a benefit to an agreement by Madigan to act on a specific matter of interest to ComEd.
Additionally, they’ve argued that Blakey erred when he let prosecutors play a recording of Madigan joking that certain ComEd contractors had made out “like bandits.” Madigan made the remark when discussing former Chicago Federation of Labor President Dennis Gannon.
Gannon was not among the five Madigan allies paid by ComEd as part of the conspiracy alleged by prosecutors. However, Blakey let jurors hear the recording after Madigan testified that he was “angry” to learn that some of the five allies did little or no work for their money.
All of Madigan’s arguments to stay out of jail “lack merit,” prosecutors say.
The question of bond pending appeal has come up in two cases related to Madigan’s prosecution. One involved James Snyder, the former mayor of Portage, Indiana. His appeal went all the way to the U.S. Supreme Court, prompting the justices’ 2024 conversation about the word “corruptly,” as well as a ruling that narrowed the feds’ use of a bribery law.
Snyder’s appeal also prompted a six-month delay in Madigan’s trial.
U.S. District Judge Matthew Kennelly agreed in December 2021 to let Snyder remain free while challenging his conviction. Snyder’s lawyers ultimately convinced the Supreme Court that the bribery law does not criminalize after-the-fact rewards known as “gratuities.”
Kennelly, who sits in Chicago but presided over part of Snyder’s case in Indiana, said at the time that Snyder had raised a “legitimate issue” because of a “split” among the country’s appellate circuit courts.
“I’m not required to say that I was wrong,” Kennelly said then. “That’s not the standard. It’s the kind of issue that, if it were granted, it would result in vacating a sentence because the sentence was premised at least in significant part on that claim.”
Questions about the word “corruptly” have also been raised in an appeal filed by developer Charles Cui, who was convicted alongside former Chicago Ald. Edward M. Burke in a prosecution prompted by the same investigation that took down Madigan.
U.S. District Chief Judge Virginia Kendall denied Cui’s motion for bond pending appeal last December, after she sentenced him to 32 months in prison. Though he argued that Kendall erred in defining “corruptly” for the jury, the judge concluded it’s unlikely the appellate court would order a new trial even if it agreed with Cui that she made a mistake.
“The trial record demonstrates that Cui ‘knew it was wrongful, or unlawful, or forbidden’ to bribe Burke,” Kendall wrote.
Cui is now in prison, and his lawyers are set to argue before the 7th Circuit in September.
Leonard cautioned against gleaning too much insight from the experiences of Snyder or Cui. Each case is “so individualistic,” he said.
But even though he said the “odds are stacked” against Madigan, he said the former speaker should take heart if the appellate court were to ultimately grant his request, letting him remain free while it hears his case.
“There’s no possibility they would do it if they didn’t think that there was a very strong, substantial legal issue being raised that could be outcome determinative,” Leonard said. “So I think it’s a phenomenal sign, if that’s what happens.”