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Jeff Tobolski Sentenced to Four Years for McCook Extortion and Bribery

The judge said his misconduct terrorized McCook’s 300 residents, noting his cooperation proved pivotal in prosecuting other officials.

Jeffrey Tobolski, County Board commissioner, at the Cook County Board meeting in Chicago on Jan. 16, 2020. (Zbigniew Bzdak/Chicago Tribune)

Overview

  • U.S. District Chief Judge Virginia Kendall handed down the four-year prison sentence on August 11, with Tobolski due to report on November 3.
  • Federal prosecutors had sought a roughly five-and-a-half-year term, but his two-year reduction reflected extensive cooperation that included unshielded grand-jury testimony and recorded conversations.
  • In 2020, Tobolski pleaded guilty to extorting more than $250,000 from businesses and associates, including $29,700 from an event-hosting restaurant on McCook property.
  • Agents seized over $51,000 in cash from his home safe during the investigation into his dual roles as mayor and county commissioner.
  • His cooperation was instrumental in securing convictions and pleas from former chief of staff Patrick Doherty, ex–Police Chief Mario DePasquale and others in the wider Chicago-area corruption probe.