Chicago City Wire

Chicago City Wire

Tuesday, March 31, 2020

Teachers union president, Sharkey, wants city homeowners to pay more in property taxes while he gets a big break on his


By W.J. Kennedy | Oct 31, 2019


Chicago Teachers Union (CTU) President Jesse Sharkey gets a discount on his property taxes, but wants other city homeowners to dig even deeper to satisfy the demands of the city's 24,000  teachers and their broke pension system. 

Sharkey pays an estimated half of the taxes he should on his Rogers Park home, records show.

The Cook County Property Tax website shows that in 2018 Sharkey paid only $9,710.40 in property taxes on his home on West Chase Avenue, which he bought in 2006 for $835,000. It is now estimated by Zillow to be worth just less than $1 million.

The County Assessor’s office, after two recent appeals on the assessed value by Sharkey, puts the 2019 market value of the house at $525,480. (Of note, CTU backed Assessor Fritz Kaegi in last November’s election.)

Sharkey would be paying $15,415.75 if the property were valued at the $835,000 price he paid for it 13 years ago. He would be paying even more on the property, $18,461, if it were valued at the Zillow estimate of $1 million – that’s 90 percent higher than what he’s currently paying in taxes.

What’s more, Sharkey’s property taxes are actually lower now than in 2011 when $10,247 was paid on the house, according to

County records show Sharkey appealed his property taxes in 2015 and in 2018, and won both times. In 2018 the assessed value on the home, which is 10 percent of the market value, was dropped from $56,580 to the $52,548 amount; and in 2015, the value dropped from $53, 293 to $50,314. Representing him on both appeals was Paul Raila, sister and law partner of Andrea Raila, who ran for Cook County Assessor last term and lost.

This while property tax collections from 2009 to 2017 for Chicago Public Schools grew nearly twice as fast as the typical Chicago family income, according to an analysis by the Illinois Policy Institute (IPI).

“Meanwhile, CPS debt grew more than six times faster than the typical Chicago family income,” the IPI study said

An August 2019 Patch article headlined “CTU Boss Talks Like Working Man, Lives Like Wealthiest 1 percent” describes Sharkey’s home as a $1.5 million Rogers Park estate. Sharkey owns the lot next door to his house, courtesy of his father-in-law, Richard Fain, a GOP supporter who owns and operates Royal Caribbean Cruises. A Fain-family trust bought the lot in 2006 for $625,000. 

“Most people don't know is that the CTU boss lives with his wife and kids in a $1.5 million Rogers Park estate — 4 bedrooms complete with a second-floor patio, a third-floor ‘master retreat,’ a sunroom and an electric car by Tesla, a non-union automaker, parked in the garage — that stretches across three lots a short walk from Lake Michigan,” the Patch article said.

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