Former McCook police chief admits demanding bribes for suburb’s mayor

McCook’s onetime police chief wore his badge and carried his gun while demanding bribes from a business owner on behalf of then-Mayor Jeff Tobolski back in February 2015. 

And when the business owner asked what would happen if he didn’t make payments of $1,000 a month, DePasquale told him it wouldn’t be good for business. 

That’s according to a 20-page plea agreement released after DePasquale pleaded guilty to an extortion conspiracy Wednesday before U.S. District Judge Elaine Bucklo. The judge set his sentencing for Jan. 5. Guidelines call for him to spend more than two years in prison.

A federal grand jury first charged DePasquale almost exactly three years ago, in September 2020. His indictment hit two weeks after Tobolski pleaded guilty to related charges. Tobolski, who agreed to cooperate with prosecutors, has not been sentenced.

DePasquale was accused in his indictment of essentially acting as a bagman for Tobolski, who admitted shaking down the owner of a McCook restaurant, starting around 2016. But DePasquale’s plea agreement also revealed an earlier extortion scheme dealing with another business based in McCook. 

That business was not identified in DePasquale’s plea agreement. It said the company was purchased in late 2014 and, afterward, DePasquale and Tobolski decided they would collect $1,000 a month by threatening to interfere with the business otherwise.

DePasquale collected $55,000 from that business owner between 2015 and 2019 and then delivered the money to Tobolski, according to the plea agreement.

The later scheme involved a restaurant that had a five-year deal to operate on McCook property, records show. Tobolski also signed off on that restaurant’s liquor licenses. But then, in 2016, DePasquale demanded that its owner pay him and Tobolski a total of $1,500 for each themed event held at the restaurant. 

The owner paid the money out of fear that the men would interfere with the restaurant’s business. DePasquale went to the restaurant multiple times to collect the payments, which he then split with Tobolski, according to the plea agreement. 

Of each $1,500 payment, $1,000 was meant for Tobolski, and $500 was meant for DePasquale. The restaurant owner paid a total of $29,700, according to the plea agreement.

DePasquale also told the restaurant owner to contribute to Tobolski’s political campaign in order to be left alone. The owner paid DePasquale $1,500 in 2017 and $1,000 in 2018 for Tobolski’s campaign, records show.

Though court records have not named the restaurant in question, the feds have seized records as part of their investigation related to a restaurant once known as The Pub at The Max — located inside a McCook-owned indoor sports complex.