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* The Tribune in 2020…
Former Cook County commissioner and McCook Mayor Jeffrey Tobolski pleaded guilty in federal court Tuesday to conspiring with a local police official to extort a restaurant owner who needed permission to host events serving alcohol.
During the hearing before U.S. District Judge Harry Leinenweber, prosecutors announced that Tobolski is cooperating with the investigation and his assistance is ongoing. Tobolski is in line for a significant break on his sentence if he cooperates fully, prosecutors said.
Tobolski admitted in a plea agreement that he collected $29,700 in cash from the extortion scheme, which involved an unidentified restaurant on McCook-owned property. […]
Tobolski also admitted in the plea that he extorted or collected bribes with at least four other people by abusing his official position as mayor or county commissioner. The amount of bribes he collected totaled at least $250,000, though the plea does not spell out how many victims were involved. […]
Tobolski, who resigned from the County Board and from his post as McCook village president in March, has been under a cloud since federal agents raided his offices in McCook nearly a year ago as part of a sweeping public corruption probe that has led to a slew of charges against Democratic lawmakers and power players. At Tobolski’s home, agents seized more than $51,000 in cash stored in a safe, according to sources with knowledge of the investigation.
* Fast forward to the present. Jason Meisner at the Tribune…
On Monday, five years after pleading guilty and agreeing to cooperate in the investigation, Tobolski is finally set to be sentenced at the Dirksen U.S. Courthouse, a place he’s never publicly appeared due to pandemic-era restrictions in place at the time he was charged.
Prosecutors have asked U.S. District Chief Judge Virginia Kendall for a 5 1/2-year prison sentence, writing in a recent court filing that Tobolski “went on an aggressive and persistent cash grab to enrich himself” at his constituents’ expense, regularly demanding cash payments and other benefits from people seeking to do business in McCook and elsewhere in the Chicago area. […]
Tobolski’s lawyers, meanwhile, are asking for leniency, pointing to his extensive cooperation in the case, which led to the successful prosecution of others. They also told the judge in a recent filing that the shame of media coverage coupled with the loss of his livelihood have already amounted to severe punishment.
* More from Sun-Times federal court reporter Jon Seidel…
Though Tobolski’s crimes might have once put him in line for a prison term of 11 to 14 years, his cooperation is expected to earn him a break at sentencing. Ardam noted in her court filing that Tobolski testified “unprotected” before a grand jury and secretly recorded conversations for the feds.
Tobolski took over as mayor of McCook in 2007 after the death of his father. He admitted in 2020 that he not only shook down a restaurant owner there, but that he’d engaged in other extortion and bribery schemes involving his two offices, agreeing to accept more than $250,000 “as part of criminal activity that involved more than five participants.”
A series of federal corruption investigations were just coming into public view when Tobolski pleaded guilty. Also charged that year were former McCook Police Chief Mario DePasquale, former state Sen. Martin Sandoval and Tobolski’s onetime chief of staff, Patrick Doherty.
Sandoval died later in 2020. But Doherty pleaded guilty in 2022, admitting to multiple corruption schemes that variously involved Tobolski, Sandoval and others. U.S. District Judge Ronald Guzman sentenced Doherty in 2023 to more than five years in prison.
* Jon Seidel reporting from the courtroom…
Ardam mentions the 51-month sentence given to Patrick Doherty, noting that it involved less money and that he wasn't an elected official.
Judge Kendall interrupts to note that Doherty's crimes were committed "over a shorter period of time," as well.
— Jon Seidel (@SeidelContent) August 11, 2025
* Tobolski addressed the court before his sentencing…
Tobolski: "In September 2019, the FBI conducted raids on both my home and the office of the mayor of the Village of McCook. The lies and the deceit had come to an end."
He says he was initially "in a state of shock and denial" — as well as "damage control."
— Jon Seidel (@SeidelContent) August 11, 2025
Tobolski says a member of the grand jury asked him whether his victims shared some level of responsibility for what happened.
Tobolski says he replied that he "was solely responsible."
— Jon Seidel (@SeidelContent) August 11, 2025
* Judge Virginia Kendall…
Kendall: "The power of this position was the thing that went to your head to start acting the way that you did."
She also says she had to look up McCook and was surprised to see it only has 300 residents
"This small community should never have been terrorized by one human being."— Jason Meisner (@jmetr22b) August 11, 2025
JUST IN: Jeff Tobolski, former mayor of suburban McCook who double-dipped as a Cook County commissioner, sentenced to 4 years in prison for shaking down people doing business in his town.
Tobolski was charged five years ago as part of a sweeping corruption probe in the suburbs pic.twitter.com/VkStlQPjZy— Jason Meisner (@jmetr22b) August 11, 2025
Tobolski is due in prison November 3.
posted by Isabel Miller
Monday, Aug 11, 25 @ 12:03 pm
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Does a village with only 350 residents really need a village president and village six trustees?
Comment by McCook Monday, Aug 11, 25 @ 12:38 pm
==which involved an unidentified restaurant on McCook-owned property==
There are maybe three restaurants in McCook.
McCook is a perfect candidate for consolidation. Lyons should absorb them.
Comment by City Zen Monday, Aug 11, 25 @ 12:55 pm
“This small community should never have been terrorized by one human being.” This situation applies to a huge amount of small towns and township governments outside Cook county. If Andrew Boutros and the AUSAs want to work, which I doubt, since Crundwell in Dixon is the only recent federal prosecution in the “other” fifteen counties in the Northern District.
Comment by Payback Monday, Aug 11, 25 @ 1:22 pm
As other commenters have suggested, this is one of the best reasons for consolidation of local governments. Tiny municipalities and uselessly redundant townships can get away with a lot of corruption, especially as local news continues to vanish.
Comment by Joseph M Monday, Aug 11, 25 @ 1:52 pm
Just because a town is small and township government works in the dark doesn’t mean it will be corrupt Dalton turned out ok didn’t it? /s. I think many of these towns should just become under county government but I don’t see any county taking on the expens. The sewer and water problems alone demand state action not to mention all the abandoned properties in some
Comment by DuPage Saint Monday, Aug 11, 25 @ 2:05 pm
Judge Kendall sentenced Ed Burke to two years of prison. She gives Tobolski four. So she thinks what Tobolski did is twice as bad? Seems a little off.
Comment by Telly Monday, Aug 11, 25 @ 2:11 pm
The feds are going to have to open an Illinois wing of a federal prison with the new additions from Illinois they will be getting here shortly.
Comment by Demoralized Monday, Aug 11, 25 @ 2:19 pm
Rich - can we please have a chart of all the pols we currently have in prison or about to go to prison, and their prison due date and release date, as well as where they are/going? There are so many now I’ve lost count (banned punctuation).
Comment by Just Me 2 Monday, Aug 11, 25 @ 3:18 pm
=McCook is a perfect candidate for consolidation=
As is Leland Grove, Jerome, Grandview, and Southern View.
Comment by Leatherneck Monday, Aug 11, 25 @ 3:18 pm