Federal prosecutors want a prison sentence of more than 5 ½ years for former Cook County Commissioner Jeff Tobolski, who they say “went on an aggressive and persistent cash grab to enrich himself” while holding elected office.
Assistant U.S. Attorney Tiffany Ardam wrote in a 12-page court filing Monday that “the sheer breadth of Tobolski’s corrupt schemes is staggering,” that he “created a vast web of corruption” by enlisting others in his wrongdoing, and that he cracked jokes about it all.
“You know I don’t take any money in McCook, ever,” Tobolski allegedly once quipped. “I’m as legitimate as they come.”
Tobolski also served as mayor of tiny west-suburban McCook. Ardam wrote that he “shamelessly shook down business owners repeatedly over the course of years” and “routinely asked for and accepted a wide variety of benefits, including cash, cigars, dinners, holiday gifts, sporting event tickets, and even free air-conditioning units.”
Criminal charges against Tobolski were highly anticipated when they were filed in August 2020. By then, he’d already resigned from his posts in Cook County and McCook, months after federal agents searched his offices.
Tobolski then pleaded guilty to an extortion conspiracy charge in September 2020. He formally agreed to work with prosecutors. Then he disappeared from public life, while the feds got to work securing prison sentences for other corrupt officials.
Now it’s Tobolski’s turn to face a judge. His sentencing hearing before U.S. District Chief Judge Virginia Kendall is set for July 16. Ardam officially asked the judge to give him 67 months. Tobolski’s lawyers were expected to make their own sentencing recommendation later Monday.
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.
Earlier this year, Tobolski’s name came up during the bribery trial of Illinois Sen. Emil Jones III. That trial, which ended with a hung jury, featured testimony from Omar Maani, a former red-light camera executive who helped the feds build cases against Tobolski and others.
Ardam’s filing Monday alleged that Tobolski once demanded a 10% kickback from Maani after Maani’s business was awarded a project in McCook. When Maani initially didn’t pay the bribe, Tobolski allegedly withheld payment of Maani’s invoices until the kickbacks were eventually paid in cash, according to Ardam’s memo.
Tobolski also got a notable reference during the 2024 sentencing of DePasquale, who wound up with a prison sentence of more than two years. Defense attorney Jonathan Minkus told U.S. District Judge Elaine Bucklo that Tobolski was “one of the most vile and corrupt people that one could possibly imagine.”
Tobolski “created in the western suburbs an almost unfathomable Wild West-like atmosphere where everybody was fair game,” Minkus insisted.
Bucklo told DePasquale “there’s just no putting the blame on the mayor,” though.
“You don’t join the corruption,” the judge said. “You go and report it.”