Politics & Government
CTU Boss Talks Like Working Man, Lives Like Wealthiest 1 Percent
Chicago Teachers Union boss Jesse Sharkey talks like a socialist tough guy, lives in a posh Rogers Park estate and drives a Tesla.

CHICAGO -- Chicago Teachers Union boss Jesse Sharkey talks like a working-class tough guy.
“This is a union that is prepared to strike,” he said after rejecting the city’s offer to boost teacher pay by 16 percent over five years, and piggyback money in the budget to boost the number of social workers, librarians and nurses.
It might even be true. Chicago teachers had a rough go of it under Rahm Emanuel. Layoffs, furloughs and budget cuts so steep that some parents donated toilet paper to local schools. You can’t blame rank-file-teachers for being fed up.
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But what makes almost everything Sharkey says difficult to believe is that the socialist union boss privately enjoys the posh life of a rich guy who can afford to walk a picket line.
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Maybe you’ve seen Sharkey's snarled lip while protesting the evils of Chicago’s elite that keep the working man down, and using his bully pulpit to rail against certain mega corporations. Chicago-based McDonalds, for instance.
“I am here to communicate the growing concerns from people across the globe regarding the devastating impact McDonald’s is having on workers, our food system, and health of our children,” Sharkey said at a 2015 McDonald’s shareholders meeting.
What 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. Go ahead, take a tour.
How can a union guy, whose wife works for a socialist non-profit book publisher, live like the wealthiest 1 percent?
It probably doesn't hurt that Sharkey’s father-in-law is Richard Fain, the Republican financier who owns and operates Royal Caribbean Cruises. Here’s one example: A Fain-family trust bought the lot next to Sharkey’s house for $625,000 in 2006, according to public records.
Not that there’s anything wrong with that.
But I think it's worth noting, particularly given his take on McDonald’s, that you don’t hear Sharkey publicly decrying the negative impact that certain corporations, Royal Caribbean for instance, has on its workers and the environment. (His father-in-law’s company got fined $750,000 for overworking crew members, and the U.S. Justice Department fined the cruise company $18 million for illegally dumping oil and hazardous waste.)
The CTU boss has a sweet way of explaining the glaring juxtaposition of his socialist tough-guy rhetoric and capitalist-funded home life. Apparently, he liked the statement so much he shipped the same lines to two different publications, two years apart.
“We don’t choose the family of our loved ones,” Sharkey told Sun-Times columnist Michael Sneed in 2015 and Chicago City Wire in 2017. “I have a lovely wife. We have children. I live in a house in Rogers Park and only have one of them, and I send my kids to public schools.”
But even that’s a bit misleading.
Sharkey, who publicly rails against the proliferation of magnet schools because of the harm he says they do to neighborhood schools, sends his kids to magnet and selective enrollment schools miles away from home even though a top-rated school is within walking distance.
Those are all kind of things that makes a guy wonder if Sharkey is a phony willing to walk working-class teachers toward a picket line to gain the kind of influence that made former CTU boss Karen Lewis a political powerhouse after the 2012 strike.
I reached out to Sharkey to ask him why I might be wrong about that, but he didn’t bother to reply.
Rank-and-file teachers should find out what really motivated Sharkey's strike threat before following him anywhere.
Mark Konkol, recipient of the 2011 Pulitzer Prize for local reporting and Emmy-nominated producer, was a producer, writer and narrator for the "Chicagoland" docu-series on CNN. He was a consulting producer on the Showtime documentary, "16 Shots."
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