How a Nebraska stockbroker built a multi-billion dollar empire and shaped American political discourse.
In short: Joe Ricketts rose from humble beginnings to found TD Ameritrade, eventually controlling the Chicago Cubs and launching diverse ventures from bison ranching to digital news. Yet, his legacy is defined as much by his aggressive political activism and controversial personal communications as by his significant financial success and philanthropic efforts.
Born in 1941 in Nebraska, Joe Ricketts transformed a $12,500 investment in 1975 into the retail brokerage giant TD Ameritrade. His career reflects a restless entrepreneurial spirit, spanning the American Film Company, High Plains Bison, and various digital media outlets. In 2009, his family acquired a controlling interest in the Chicago Cubs, eventually witnessing the team break a 108-year championship drought in 2016. Despite his business acumen, Ricketts has faced significant public scrutiny, particularly regarding his management style and personal views.
Ricketts’ political involvement has been both prolific and polarizing. In 2010, he founded Taxpayers Against Earmarks, later rebranded as Ending Spending, to challenge federal fiscal policies. His political action committees have spent millions to influence elections, often targeting incumbents. However, his methods have drawn fire; in 2012, a leaked proposal suggested an aggressive $10-million ad campaign against Barack Obama, which Ricketts’ organization ultimately rejected as a nonstarter. His shifting allegiances—moving from opposing Donald Trump in the 2016 primaries to donating over $1 million to his general election campaign—underscore the pragmatic, if controversial, nature of his political engagement.
The most significant reputational challenge occurred in 2019 when Splinter News published a cache of his emails from 2009 to 2014. The correspondence contained inflammatory remarks about Islam, conspiracy theories regarding Barack Obama, and racist jokes. Ricketts issued an apology following the disclosure. This incident sits alongside his 2017 decision to shutter DNAinfo and Gothamist just one week after staff voted to unionize, citing his belief that unions foster a corrosive environment. Today, Ricketts continues his work through ventures like Straight Arrow News and various foundations, maintaining a complex footprint that bridges high-stakes finance, professional sports, and the volatile landscape of American political and social debate.
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