On this date, 11 July 1988, Mike Tyson, then World Heavyweight Champion hires Donald Trump as an advisor.

Trump, who is now the current US President had two days earlier told The New York Times that “Mike Tyson has asked me and I have agreed, to serve jointly, with regard to future decisions about Mike Tyson’s career, including but not limited to the lawsuits going back and forth between Mike and his current manager, Bill Cayton.”

Donald Trump and Mike Tyson on this date, 11 July 1988

This pairing happened within hours of Mike Tyson shocking the world with his 91-second knockout victory over till undefeated heavyweight boxer Michael Spinks. Tyson fired Bill Cayton ending four-year contract.

Trump at the time was a real estate mogul. It didn’t seem outlandish that the brash Tyson would look to the brash Trump for financial advice. Trump, however, also intended to manage Tyson’s boxing career — though the story notes he intended to hire a boxing expert to help with those decisions.

It was later revealed that Trump had made millions as the live-site promoter of three Tyson title fights and there was considerable conflict of interest involved in Trump’s new “adviser” role.

Trump later billed Tyson $2 million after the boxer dropped him to work with Don King. Donald Trump spent $11 million on Mike Tyson-Michael Spinks 91-second fight in 1988 to promote his casino business. He made a total revenue of $26 million on the night of the bout.

Despite their eventual breakup, Tyson surprisingly supported Donald Trump in the run-up to the 2016 presidential election. “Let’s run America like a business, where no colours matter,” the former heavyweight champion said.