James Sharkey lives in Rogers Park, Chicago with his wife Julie Fain and their two children who have grown up in the CPS system
The union boss at the center of Chicago’s school shutdown firestorm is a longtime labor activist and supporter of socialism, but critics say his lifestyle is more akin to that of the wealthiest 1 percent.
Living in an expansive $1.5 million estate on multiple adjoining lots in Rogers Park, Chicago Teachers Union President Jesse Sharkey is said to drive a Tesla and is married to the daughter of Royal Caribbean Cruises’ recently resigned CEO.
On Tuesday, 52-year-old Sharkey led his union members in a vote to refuse in-person instruction starting immediately, citing concerns over the rapid spread of the Omicron variant.
It led to a chaotic total shutdown of schools announced at 11pm the prior night, as the school system said it did not have the systems in place for virtual instruction.
Sharkey, who has led the CTU since 2014, said on Wednesday that teachers would only return to classrooms after the current surge subsides, unless the district agrees to the union’s demands for new testing and health protocols.
‘If you want to get us into the schools quicker, provide testing,’ Sharkey said at a Wednesday news conference.
‘We’ve been failed by the mayor, we’ve been failed by the public health office, and teachers and the school staff have decided the only thing we have control of is whether we go into the buildings.’
Sharkey did not immediately respond to an inquiry from DailyMail.com on Wednesday.
The stunning drama in the nation’s third-largest public school system, with an enrollment of more than 350,000, has thrust longtime Chicago activist Sharkey into the national spotlight.
In the past, Sharkey’s lavish lifestyle has drawn criticism from his opponents, and speculation that his wealthy and decidedly capitalist father-in-law is helping to bankroll his family.
Chicago journalist Mark Konkol wrote in a 2019 column for Patch that Sharkey ‘talks like a working-class tough guy’ but drives a Tesla and lives in a luxurious five-bedroom home.
‘How can a union guy, whose wife works for a socialist non-profit book publisher, live like the wealthiest 1 percent?’ wrote Konkol.
Raised in central Maine by his mother, a poet and schoolteacher, Sharkey attended Brown University, where he majored in modern American history.
After graduating, Sharkey went into labor organizing with the United Steelworkers in North Carolina, before returning to Brown for a master’s degree in teaching.
While teaching high school social studies in Providence, Rhode Island, Sharkey met his now-wife Julie Fain, the daughter of business executive Richard Fain, who has an estimated net worth of nearly $200 million.
Richard Fain on Monday resigned as CEO of the Royal Caribbean Group after a 33-year tenure, in a move that was part of a succession plan announced in November.
Sharkey’s father-in-law Richard Fain (above in 2013) was the third-longest serving CEO among current S&P 500 leaders when he retired on Monday
In a statement to Chicago City Wire in 2017, Sharkey said: ‘We don’t choose the family of our loved ones.’
‘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,’ he said.
Sharkey and Julie Fain moved together to Chicago, where she worked as an editor for the leftist magazine In These Times before co-founding radical independent book publisher Haymarket Books.
The couple share two children, Caleb – a graduate from Jones College Prep, a public school, and Leo, who was at one point a student at Harriet Tubman elementary school – both Chicago Public Schools.
In a photo obtained by DailyMail.com where the family is pictured on a trip to Disneyland, the oldest son is seen wearing a t-shirt with a Mustangs logo – the official name used for sports teams at St Rita of Cascia, a $13,000-a-year private, all-boy’s Catholic school in Chicago.
Public records show that Sharkey and Fain own a $868,000 home in Rogers Park, and that his wife’s family trust bought the adjacent lot for $625,000 in 2006.
Meanwhile Sharkey continued teaching and became increasingly involved in the teachers union, as well as far-left political groups.
He was a member of the International Socialist Organization, a Trotskyite group that opposes capitalism, until the group dissolved in 2019 over allegations that its leadership mishandled a sexual assault accusation.
From 2008 to 2013, Sharkey was an occasional contributor to the ISO publication SocialistWorker.org.
In 2012, when he was vice president of CTU, Sharkey appeared shaken when his attendance at the Midwest Marxism Conference was raised in an interview on local radio station WLS-AM.
‘Every time unions have raised issues about what’s fair and what isn’t, and equality, people have branded them as Communists,’ Sharkey replied.
Pressed on whether he agreed with the tenets of Marxism, Sharkey dismissed the interview as a ‘witch hunt’ and said: ‘I’m allowed to attend a Marxist conference.’
In 2019, Sharkey landed in hot water again when a group of Chicago teachers calling themselves a ‘Chicago Teachers Union delegation’ met with officials in socialist Venezuela.
The four teachers documented their trip online and heaped praise on Venezuelan President Nicolás Maduro, whose administration was accused in United Nations reports of ‘grave’ human rights violations.
Sharkey downplayed the incident and tried to distance the union from the controversy.
‘Members go all kinds of places in the summer,’ he told WTTW at the time.
‘This was neither an official trip nor something that was funded by the union. This is a group of people who are members of the CTU who decided to go to Venezuela.’