Nobody is immune to Michael Jordan’s infamous traits. Trash-talk? He’ll take it personally. Can’t wager a bet against him? He’ll gladly sponsor you for bragging rights. Not a pro athlete on any pitch? Doesn’t matter. The ever-competitive Black Cat once even challenged a caddy to make him eat his words. ESPN’s David Kaplan was a witness. He’s been Jordan’s opponent on the greens many times. And his fierceness has intimidated Kap every time. On Stacey King’s Gimme the Hot Sauce podcast, the media veteran narrated an incident when he was playing some high-stakes golf with His Airness and four others.

As a staple in Chicago’s sports media, Kaplan was a regular at a local golf club where Jordan used to play. Kap had a young 20-year-old man as his caddy every time. At that time, Jordan was not particularly in form. Kaplan said he had an “insane” short game in putting. But when Jordan swung way past the tee, the caddy told Kap, “Wow, Michael Jordan hits the ball like a b****.”

Unfortunately, Jordan heard it even 20 feet away. He turned with his cigar, ran across the fairway, and got in the young man’s face. Despite the caddy’s attempt to diffuse the situation, Jordan demanded his handicap, threw down his bag, and challenged him to a round of golf. “Meet me on the first tee, we’re playing for $2,000 a hole right now.” When the kid said he didn’t have that kind of money, Jordan presented a different kind of bet.

Kap further revealed, “‘I don’t want your money. If you beat me, I’ll pay you $2,000 a hole right here. I got the money in a safe in my trunk,’ he said. ‘But when I beat your a**, you see that 100 members over there by the patio on this beautiful July day, you’re going to get down on your knees in front of them and you’re going to call me daddy in front of every one of them.’”

Any NBA players who lost to Jordan should be grateful they didn’t have the same bet going on in a dunk contest because Kaplan said that Jordan not only “destroyed” the kid, he walked the kid over to the club members that boasted a few Bulls players, “the kid got down on his knees, he goes ‘I’m so sorry for doubting you, daddy.’” He should be lucky he wasn’t in Kap’s place.

ESPN veteran made the same mistake against Michael Jordan
Around 2020, Jordan and Kaplan went 36 holes in a match. The Chicago Tribune Live host recalled later that MJ talked trash throughout but he too underestimated him. When Jordan bet him $50 a putt, Kap made the mistake of saying, “Dude, I’m not the Jazz and this isn’t a basketball court. I’ll take the bet.”

Who knows if the caddy incident was before or after, but there’s no excuse for Kap to fall for Jordan’s bets over and over. The score was MJ; 74-74, and Kap; 80-81. Kap’s takeaway was when playing golf with Jordan, always bring cash. Many would agree.

Stay tuned for more such updates and join us in the exciting pilot episode of the “Dual Threat Show” as our host BG12 sits down with Georgia Bulldogs star and SEC All-Freshman Team Selection, Silas Demary Jr.