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‘Libertarian Rex’ Digs Deep Into Sinquefield’s Political Ambitions — And Failures

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Jesse Rubenfeld Illustrations
Jesse Rubenfeld Illustrations
Devin Thomas O’Shea’s chess-themed essay for Current Affairs details “how ‘the king’ of St. Louis was defeated — for now — and how you too can topple your local hometown billionaire.”

For well over a decade, ever since he returned to his hometown, Rex Sinquefield has had an outsize influence on the St. Louis region — whether he’s pushing a city-county merger or turning the Central West End into a world capital of chess. And for much of that time, fellow St. Louis native Devin Thomas O’Shea has been watching to see what the libertarian billionaire’s next moves might be.

O’Shea first became interested in Sinquefield’s life and career in 2012. A University of Missouri-Columbia student in need of an internship to graduate, O’Shea landed an unpaid gig at the Sinquefield-funded Children’s Education Alliance of Missouri. Going in, he knew little of the organization’s privatization commitments.

In a newly published deep dive for Current Affairs, O’Shea recalls that he never got to know either Sinquefield or Travis Brown, the political operative who ran Sinquefield’s public affairs company, Pelopidas.

“I never met The King or Travis Brown, but then, I was a bad intern,” O’Shea writes. “Only a select few got invited out to Sinquefield’s 1,000 acre farm in Westphalia, Missouri for a chat about the future. I was better suited to stuffing envelopes with instructions for the local aldermen, lobbying for changes in the education system that, at the time, I didn’t understand.”

His April 14 Current Affairs essay traces Sinquefield’s trajectory, shedding light on his remarkable path from a Normandy, Missouri, orphanage to enormous wealth, even while it provides insight into St. Louis history. It’s titled “Libertarian Rex: How ‘the king’ of St. Louis was defeated — for now— and how you too can topple your local hometown billionaire.”

“One of the things that I really tried to get to in the piece is just that part of the ideology that Rex has is that he can just use his money to shape the region.

“But St. Louis is an extremely complex political landscape, with lots of different players and lots of different motives. And I think that was one of the things I think that is unique about St. Louis is the history, the fractured lines and sort of these chronic problems that really can't be solved by just one guy coming in,” O’Shea said on Monday’s St. Louis on the Air.

‘Libertarian Rex’ Digs Into Sinquefield’s Political Ambitions — And Failures
Devin Thomas O'Shea talks with host Sarah Fenske about his Current Affairs essay titled “Libertarian Rex: How ‘the king’ of St. Louis was defeated — for now— and how you too can topple your local hometown billionaire.”

As O’Shea’s story details, a striking number of Sinquefield’s initiatives have ultimately proved unsuccessful, and last September, he publicly split with Brown and Pelopidas, effectively shutting down the company. Now, as he focuses on other donations, his political ambitions seem to be waning.

St. Louis on the Air reached out to Rex Sinquefield’s spokesperson for a comment. His representatives

pushed back on O’Shea’s piece, noting that the Sinquefields were never reached for comment (which O’Shea confirmed on the air).

Sinquefield’s wife, Jeanne, also issued a lengthy statement in response to the piece, noting some minor errors in O’Shea’s piece and defending the couple’s political work.

“While some see failure in some of our projects, we see change. The Better Together project resulted in the creation of a Board of Freeholders approved by St. Louis, which has the authority to present ballot initiatives to approve a merger of the city and county,” Jeanne Sinquefield wrote. “Also, Missouri citizens approved a ballot measure to limit future counties and cities from imposing earnings taxes, allowing voters in the cities of St. Louis and Kansas City to approve the renewal of earnings taxes every five years.”

Jeanne Sinquefield did not address whether Sinquefield intends to continue his political efforts. But, she added that their philanthropy efforts for area schools remain steadfast.

“We strongly support education for Missouri students in public schools (including traditional and charter), in private schools and through virtual learning. For example, we support musical composers from kindergarten to university through the Mizzou New Music Initiative. We also support research on education through the Show Me Institute and Saint Louis University Research Institute. In addition, we provide funding for scholarships through the Today and Tomorrow Education Foundation and a number of other organizations. We also fund the St. Vincent Home for Children, an orphanage in north St. Louis where Rex grew up. By the way, our annual Christmas party is actually a fundraiser for St. Vincent’s. We provide the party, food and booze and all donations go to St. Vincent’s. Even the politicians have to donate.”

Devin Thomas O'Shea
In addition to the life and influence of libertarian billionaire Rex Sinquefield, Devin Thomas O’Shea (pictured) has written in depth about St. Louis’ mysterious Veiled Prophet tradition.

O’Shea acknowledged the couple’s philanthropic efforts but reiterated his opposition to relying on charity instead of robust public funding for services.

“The problem that we always get into with sort of neoliberal ways of redistributing wealth through charities is that we always have to come to rich people on their terms and ask for things like access to art, or sports or culture. And that's not really how culture should work,” he said.

O’Shea, a 2018 graduate of Northwestern University’s MFA program in creative writing, has had his writing published in outlets that include Boulevard, Paterson Literary Review and Belt Publishing’s anthology of St. Louis-focused essays. He’s also written an as-yet-unpublished novel that centers on the Veiled Prophet tradition.

St. Louis on the Air” brings you the stories of St. Louis and the people who live, work and create in our region. The show is hosted by Sarah Fenske and produced by Alex Heuer, Emily Woodbury, Evie Hemphill and Lara Hamdan. The audio engineer is Aaron Doerr.

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Evie is a producer for "St. Louis on the Air" at St. Louis Public Radio.

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