Before she sentenced the man who corrupted the dual offices he once held as a Cook County commissioner and mayor of tiny southwest suburban McCook, a federal judge summed up Jeff Tobolski as a “Jekyll and Hyde human being.”
Tobolski’s elixir turned out to be the power of his office, U.S. District Chief Judge Virginia Kendall said. He needed his ego stroked. And it ultimately turned him into someone so unrecognizable to his family that his own daughter said she “despised” him during his time in office.
Though Tobolski managed to repair that relationship, the judge also made note of the black mark he’d left on the suburb he once led. Then, she handed him a four-year prison sentence Monday for a series of extortion and bribery schemes that ended his political career.
He’s due in prison Nov. 3.
Tobolski spoke to the judge for more than 15 minutes before learning his fate. He apologized to his victims and family members, and he explained how a prosecutor once helped him understand his crimes by asking him to think about how he’d used his public office.
Tobolski admitted he’d become “smug, arrogant, impatient and criminal” as an elected official.
And, with a crowd of supporters seated behind him, Tobolski told the judge, “I think about this every day. I have a responsibility to make this right. And I will strive to do so.”
Tobolski, 60, found himself at the center of a federal public corruption investigation in 2019, which went public when FBI agents conducted a series of raids on several locations that included Tobolski’s home and McCook’s village hall.
He wound up pleading guilty to an extortion conspiracy in 2020, admitting he accepted more than $250,000 through a series of bribery and extortion schemes. But he also agreed to cooperate with prosecutors and disappeared from public life in the meantime.
Now Tobolski’s sentencing hearing has revealed new details about what went on behind the scenes. Assistant U.S. Attorney Tiffany Ardam told Kendall on Monday that Tobolski read a 61-page statement to a grand jury and met with federal authorities 19 times.
Tobolski defense attorney David Sterba insisted the Democrat told the feds “everything he knew and answered every single question they had.” He said Tobolski worked with them from October 2019 until May 2022 and helped make seven secret recordings.
Ardam noted that Tobolski helped with the prosecution of his former chief of staff, Patrick Doherty, and former McCook Police Chief Mario DePasquale. Doherty is serving a prison sentence of a little more than four years after admitting to multiple corruption schemes.
DePasquale was sentenced to more than two years in prison for helping Tobolski extort a McCook restaurant owner.
Ardam sought a sentence of roughly 5 ½ years for Tobolski, arguing that he “isn’t just a corrupt politician whose victims are society at large or taxpayers generally.”
Rather, she said his victims were “real, everyday people who will forever remember his crimes.”
The prosecutor also made a veiled reference to Tobolski’s “first corrupt act,” which she said took place in 2007 and involved a “scheme already set up for him.”
Tobolski took over as mayor of McCook that year following the death of his father. He won election to the Cook County Board in 2010.
Sterba argued for a lesser punishment, pointing to a series of recent corruption sentences that included the two-year prison sentence Kendall gave to former Chicago Ald. Edward M. Burke in 2024.
Kendall said federal guidelines actually called for a lower sentence for Burke than Tobolski.
But the judge said the most striking evidence before her Monday turned out to be a pair of letters from Tobolski’s wife and daughter. They described, in blunt and honest terms, how politics had transformed Tobolski.
Tobolski’s daughter said she “loathed” and “despised” him while he held public office. His wife derided people who became “nauseatingly deferential” to him and laughed “uproariously” at jokes she didn’t find funny.
“I had lost him to politics rather than the cliche ‘other woman,’” she wrote. “I rarely saw him and when I did he was often hungover and grumpy. He was no longer the Jeff I knew.”
But Tobolski’s daughter said he wound up apologizing to her. He promised to do the right thing and atone for the damage he’d done to their family.
“This man managed to dissolve years of built up hatred for him in my heart by proving almost every single day that he meant it when he said he would change, that he really was unaware of how far he had fallen,” his daughter wrote.
“The most shocking part? I actually believe him now.”
Kendall said Tobolski’s ability to repair that relationship displayed the transformation and rehabilitation he’d undergone in the years since he left office.
“You do realize,” she asked before handing him his prison sentence, “that you could have easily lost both of them?”
Tobolski agreed.