“I Think I Kicked Your A** Today”: Kevin O’Leary Recalls Losing to Tom Brady Over One-of-a-Kind Super Bowl Watch

Tom Brady’s reputation for collecting luxury watches has almost become just as prominent as his affinity for collecting Super Bowls, so football fans certainly won’t be surprised to hear that he has a few one-of-a-kind pieces to commemorate his victories on the football field. Unfortunately for Kevin O’Leary, however, he wasn’t privy to this until he had already entered an unofficial contest with Brady himself.

“This was a watch contest,” O’Leary recalled. “Brady, Jay-Z, and I thought, what could I wear that could totally kick ass?” The businessman and TV personality ultimately selected a Cartier Crash for the event, thinking no one would be able to outdo its rarity.

Once he was at the event, he proudly proclaimed to the former New England Patriot, “Brady, I think I kicked your ass today.” The seven-time Super Bowl champion proceeded to immediately remind O’Leary that there are, in fact, levels to the game.

“He said, ‘No. I have a one-of-a-kind AP with the Super Bowl wins at the 11 o’clock mark.’ I went, ‘Oh, f**k.'”

The watch itself turned out to be a custom rendition of an AP Royal Oak Flying Tourbillon. The Super Bowl wins that Brady referred to in O’Leary’s story are actually made of sapphires, and the entire face of the piece is outlined with even more precious gems.

From his $317,619,794 career earnings in the NFL to his $375-million contract with Fox Sports, the king of football certainly has no shortage of funds, and he seems more than content with converting them into luxury timepieces.

Whether he’s out partying with Patrick Mahomes or sitting in the hot seat for his Netflix Roast special, Brady’s always left a subtle yet appropriate reminder on his wrist. When it came time for his first official Super Bowl broadcast with Fox, he made sure to honor the occasion by stepping out in a $740,000, diamond- and yellow-sapphire-studded Jacob & Co. Caviar Tourbillon wristwatch.

In addition to its over-the-top price tag, this particular watch is also touted for its extreme rarity.

Given his level of fame and cultural significance, Brady even found himself on the receiving end of some rather luxurious gifts, such as the time when he received a text message from François-Henry Bennahmias, the  CEO of Audemars Piguet himself.

“My friend texted me out of the blue and said, ‘I want to create something for you… Why don’t you work with my friend and designer at Audemars Piguet, Michael Friedman, and figure out what you want to come up with.”

Suffice to say, it pays to have friends in high places. In fact, the end result of that conversation with Bennahmias proved to be the very watch that checked O’Leary’s ego that day at the competition, proving that if you’re going to go against Brady, you better be bringing some serious heat.