Former McCook mayor and Cook County Commissioner Jeff Tobolski has been recommended for a prison sentence of more than five years by federal prosecutors who filed a 12-page report Monday.
Tobolski, who pleaded guilty to an extortion conspiracy charge in September 2020, was originally scheduled to be sentenced this week by U.S. District Chief Judge Virginia Kendall. That sentencing date has since been moved to August 11.
Assistant U.S. Attorney Tiffany Ardam wrote in the court filing that “the sheer breadth of Tobolski’s corrupt schemes is staggering.” She said he “created a vast web of corruption” by enlisting others in his wrongdoing, and that he made jokes about the corruption.
Ardam wrote that as mayor of McCook he “shamelessly shook down business owners repeatedly over the course of years.” He also “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.”
Tobolski agreed to work with federal prosecutors after his arrest, which may save him from years in prison. His guilty plea would make him eligible for a prison term of 11-14 years, per federal sentencing guidelines.
Ardam noted in her court filing that Tobolski testified “unprotected” before a grand jury and secretly recorded conversations for the feds.
After pleading guilty, Tobolski was joined by former McCook police chief Mario DePasquale, former state Sen. Martin Sandoval and Tobolski’s former chief of staff Patrick Doherty who were all charged with federal crimes.
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.
In 2024, U.S. District Judge Elaine Bucklo sentenced DePasquale to a prison sentence of more than two years .
Earlier this year, Tobolski’s name came up during the bribery trial of state 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.
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.”
Tobolski’s lawyers are expected to make their own sentencing recommendation this week.
He stepped down as mayor and commissioner in 2020 before the feds made their arrest. He was succeeded as mayor by Terry Carr and as county commissioner by Frank Aguilar.