Donald Trump May 25, 2023; Washington, DC, USA; Former President Donald Trump watches his tee shot on the ninth hole during the Pro-Am tournament as part of the LIV Golf Washington D.C. 2023 event at Trump National Golf Club outside Washington DC. Mandatory Credit: Geoff Burke-USA TODAY Sports

As Donald Trump gears up for a rematch with Joe Biden in the upcoming presidential election, he’s being challenged to a golf match by Rick Reilly.

Last week, the former president proudly boasted about winning the Club Championship and the Senior Club Championship at Trump Golf Palm Beach. “A great honor to have won both the Club Championship and the Senior Club Championship this week at Trump International!” the 77-year-old wrote on Truth Social and Instagram. In response, former Sports Illustrated columnist Rick Reilly urged the former president to hold on boasting about any further golf accomplishments until they take place at a course other than one of his own.

Reilly later joined MSNBC’s Nicolle Wallace for an interview on Deadline White House, where he retold stories about Trump allegedly cheating at golf. Reilly alleging Trump’s golf game has been aided by interference is not new. It began in 2003, when Reilly griped about Trump’s golfing in his book Who’s Your Caddy. Their golf feud was ramped up in 2019 when Reilly wrote Commander in Cheat, where he claimed Trump “throws it, boots it, and moves it. He lies about his lies. He fudges and foozles and fluffs.”

After Reilly went on MSNBC to retell some of those cheating stories about Trump, a spokesperson for the Republican presidential candidate told People “Rick fantasizes about having a golf game as good as President Trump.” To that, Reilly suggested they settle it on the course to the tune of $100,000. Just not one of his courses.

“I bet $100k I can beat Trump on a course he DOESN’T own w/ USGA rules officials watching. (Hey, some white-collar prisons have courses.)” Reilly tweeted.

Last year, Trump challenged Biden to a “test of strength” and he previously claimed he could beat the 81-year-old president in a boxing match, so he’s clearly not averse to athletic contests. Rick Reilly might not move the needle enough for the former president to put his golf skills on display, but if anyone from The Match is paying attention, give these two a shout. Regardless of how you feel about his politics, unfiltered footage of a mic’d up Donald Trump at the golf course would be must see content.

[Rick Reilly]

About Brandon Contes

Brandon Contes is a staff writer for Awful Announcing and The Comeback. He previously helped carve the sports vertical for Mediaite and spent more than three years with Barrett Sports Media. Send tips/comments/complaints to