We’ll never understand guys like Jeffrey Tobolski. Here’s a guy who seemingly has it made. He inherited his job of McCook mayor – passed down to him from his father – earned salary and benefits approaching six figures (and more for serving as liquor commissioner) as mayor of a town of about 225 people.

In 2010, he set his sights on becoming a county commissioner and unseated Tony Peraica for the job of representing the 16thDistrict, whose boundaries have changed since he took over, but have included parts or all of Riverside, Brookfield and North Riverside during his years in the job.

He breezed to re-election in 2014 and 2018. He had two jobs for life – with pensions to boot. But he wanted more and shook down a restaurant owner in his hometown for cash in exchange for selling liquor at special events at The MAX, a property the village owned.

In a story the Landmark published in the run up to the 2010 county board election, we asked a question:

“Is Jeffrey Tobolski a can-do legislator who through hard work and shrewd deal-making has started a commercial renaissance in the midst McCook’s obsolete industrial past, or he is bought and paid for by a political machine that is responsible for making county government a sinkhole of patronage and corruption?”

Peraica did himself no favors in paving the way for his 2010 defeat – he had a penchant for grandstanding that alienated colleagues on the county board and right before the election was comically arrested for allegedly damaging a Tobolski campaign sign in McCook and dramatically filed a federal lawsuit in its wake – but he had a pretty good read on Tobolski.

“Tobolski represents exactly what’s wrong with public office,” Peraica said at the time. “He’s only interested in self-aggrandizement and his own benefit.”

After pleading guilty to conspiracy to commit extortion and filing a false tax return, Tobolski faces significant prison time – between 11 and 14 years – though that will probably be reduced considerably depending on how much he cooperates with federal prosecutors, who remain active in their probe of corrupt local, state and county officials and their political contributors.

Turns out that in addition to shaking down the McCook business owner for some $30,000, Tobolski accepted bribe and extortion payments in excess of $250,000, according to his federal plea agreement.

Maybe he and other small-town officials think no one’s paying attention. They get greedy, and careless.

That gravy train is now over for Tobolski and is about to be over for others as well. We hope a few years living the high life, smoking cigars like a big shot and getting envelopes full of cash was a thrill, because it was never going to last.

Will those who replace guys like Tobolski learn from these hard lessons? We sure hope so, but we’ve also seen this show over and over.