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‘It's like you're paying a little tax': Jeffrey Tobolski, ex-McCook mayor and Cook commissioner, faces sentencing in series of shakedowns
Jeffrey Tobolski's traveled a well-worn path in Chicago-area politics, from following in the footsteps of his late father as mayor of the tiny west suburban town of McCook to double-dipping as a Cook County commissioner.
But Tobolski's career also had another familiar, darker ring to it. For years, federal prosecutors say, he used his elected offices to create a fiefdom of graft, shaking down business owners who needed liquor licenses, forcing a developer to install air conditioning in his home for free, and even enlisting McCook's police chief as his personal bag man.
After the FBI raided Tobolski's offices in the fall of 2019, he became the poster boy in a burgeoning federal corruption probe that eventually brought down nearly a dozen suburban elected officials and political operatives, including Tobolski's chief of staff and other close associates.
The case unfolded like a cliched version of mid-level Chicago corruption: the wired-up executive entertaining politicos at his suburban cigar lounge, secret contracts siphoning funds from red light cameras to a mob-connected businessman, and a mayor handing over an envelope of bribe money at a Crestwood pancake house called Stacked.
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 did this by misusing the inherent authority of his position to instill fear (in) everyday businessmen, such that they felt they had no choice but to pay Tobolski,' Assistant U.S. Attorney Tiffany Ardam wrote.
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.
'Any general deterrent effect of this case has already occurred, meaning that the type and length of his sentence will add little to no marginal general-deterrent value,' wrote attorneys James Vanzant and David Sterba.
In all, Tobolski admitted to accepting more than a quarter of a million dollars in bribes or extortion payments over the years. He also was showered with a variety of other benefits, including cash, cigars, dinners, holiday gifts, sporting event tickets, and those free air-conditioning units, which a developer installed at Tobolski's home at a cost of $18,000.
During the investigation, Tobolski was secretly recorded joking about how corrupt he was, prosecutors say, at one point stating sarcastically, 'You know I don't take any money in McCook, ever. I'm as legitimate as they come.'
His then-chief-of-staff, Patrick Doherty, was caught on another wiretap talking with an associate about the prospect of doing business in Tobolski's notoriously corrupt administration.
'It's all contingent on what you can give,' Doherty told the associate, Omar Maani, about the obligatory campaign donations to Doherty's boss, according to court records.
Maani, who was secretly recording the September 2019 conversation for the FBI, said, 'It's like you're paying a little tax.'
'Right. Juice,' Doherty replied, according to court records. 'Street juice….I hope we can get it before (Tobolski) goes to jail. I hope we can retire.'
Tobolski, 60, pleaded guilty in September 2020 to conspiring with McCook's then-police chief, Mario DePasquale, to extort a restaurant owner who needed permission to host events serving alcohol. At the time, Tobolski doubled as McCook's liquor commissioner.
Tobolski also pleaded guilty to filing a false tax return in 2018 where he underreported his income by at least $66,000, at least $10,000 of which was bribe money, according to his plea agreement. The document stated he also misreported his income in returns filed each year from 2012 to 2017.
In their memo asking for a 67-month prison term, prosecutors called Tobolski's use of his police chief as his bagman 'especially egregious.'
At DePasquale's sentencing hearing last year, the victim, the former owner of the Pub at the Max facility in McCook, testified how in July 2018, after he'd come up short with a payment, DePasquale warned him that the boss would not be happy. The man said his license was revoked by the city the next day, putting him out of business.
'That was one of the worst days I have in my life,' the victim testified in a thick Greek accent.
DePasquale's attorney said his client felt compelled to go along with Tobolski, whom he called 'one of the most vile and corrupt people that one could possibly imagine.'
'He created in the western suburbs an almost unfathomable, Wild West-like atmosphere, where everybody was fair game for them,' attorney Jonathan Minkus said. 'And the mayor made it clear to DePasquale from the get-go that if he refused to go along, he'd lose his job.'
Tobolski is one of the last to be sentenced in a probe that stretched from Chicago's southwest suburbs to the Capitol building in Springfield, where federal agents raided the offices of then-state Sen. Martin Sandoval in September 2019, thrusting the case into the public spotlight.
Two days later, agents fanned out across the suburbs, executing search warrants at village halls and the homes of several elected officials, including Tobolski, where they found $51,000 in cash stored in a safe. Tobolski resigned from his elected positions the following March.
At the center of the case was Maani, a then-executive for red light camera company SafeSpeed LLC who worked undercover for the FBI for months and wore a wire on several defendants — including Sandoval, Tobolski, Doherty, and then-Crestwood Mayor Louis Presta — all of whom he hosted at his Countryside cigar lounge called Casa De Montechristo.
Maani, who was given a deferred prosecution agreement for his efforts, also recorded state Sen. Emil Jones III and testified for the first time at Jones' bribery trial earlier this year.
Maani told the jury he started bribing elected officials when he was still in his 20s, making money hand-over-fist as a real estate developer and SafeSpeed co-founder. To him, it was the necessary way to do business in Illinois, he said.
'I gave them cigars, took them out to dinner, gave them campaign contributions,' Maani said of his corrupt ways. 'They always asked me for money. I capitulated and gave it to them.'
Who asked him for money? a prosecutor asked.
'Virtually everyone, from what I recall,' Maani said.
The jury in Jones' trial deadlocked on all counts, and a retrial is set for January.
Sandoval, the once-powerful head of the Senate Transportation Committee, pleaded guilty to taking tens of thousands of dollars in cash over a two-year period from Maani to serve as SafeSpeed's protector in the Senate. He was cooperating with the government when he died suddenly of COVID-19 complications in December 2020.
Doherty and Presta also pleaded guilty and were sentenced to prison.
SafeSpeed and its CEO, Nikki Zollar, have said they were not aware of Maani's illegal activities and have not been accused of any wrongdoing.
As part of their sentencing submissions, Tobolski's lawyers filed numerous awards and other accomplishments from his career. They also sent the judge two heartfelt letters from Tobolski's wife and daughter, who talked at length about how he got into politics with seemingly the best intentions, but changed into someone they barely knew.
'I'd attend a political event with him and people would be so nauseatingly deferential to him that I had to actually concentrate to not make a face,' wrote his wife, Cathleen. 'They'd laugh uproariously at a joke that wasn't even funny.'
Tobolski's daughter, who was a freshman in college at the time news of the investigation broke, wrote that she'd 'loathed' her father for dragging her to funerals and introducing her to 'a LOT of creepy drunk men' at political events.
'I resented him because I remember being told that any mistake I made in my own life would reflect poorly on him as a politician, that our lives were public and there would always be some political foe or reporter that would jump at the chance to use our family's missteps as leverage against him,' Tobolski's daughter wrote.
In asking for leniency, Tobolski's wife and daughter both commended his decision early on to not fight the charges and cooperate, and said he's since made amends and rededicated himself to his family.
'The heart of the matter is that we just got him back,' his daughter wrote.
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