Ric Flair Gifted Custom Rolex Recreating Shawn Michaels’ WrestleMania Gift

Ric Flair received an emotional surprise at the National Sports Collectors Convention this week when luxury watch dealer Roman Sharf presented the WWE Hall of Famer with a custom Rolex designed to recreate a piece of wrestling history.

The watch was modeled after the Rolex Shawn Michaels reportedly gave Flair following their iconic retirement match at WrestleMania 24 in 2008 — one of the most emotional bouts in WWE history, capping Flair’s in-ring career on WWE television. Flair is said to have lost track of that original timepiece over the years, and the gesture from Sharf was meant to replace what had become a meaningful, if misplaced, memento.

Footage of the surprise spread quickly online, with the original video topping three million views. Flair shared his own gratitude on social media, writing that the moment left him ​very emotional.

Speaking on his Dual Time podcast, Sharf detailed how the idea came together almost by accident. He explained that Steven Solomon, who handles Flair’s appearances and autograph signings, was at his shop picking up a watch when the story of the missing Rolex came up in conversation. Solomon mentioned it would be nice to replace it someday, and Sharf said the idea clicked instantly given the timing of the upcoming convention.

​“This wasn’t even planned,” Sharf said. “He told me this whole story about how Ric Flair misplaced the watch and the whole to-do… I was like, ‘Why are we going to wait? I’m going to go, take a payday, have a custom dial made, and I’ll give it to him at The National as a surprise.’”

Sharf said he didn’t know what reaction to expect, but Flair’s response affected him deeply. ​“His emotional reaction got me emotional,” he said. ​“I felt like I made a legend’s day. You can see him trying to get out a ‘Wooo!’ and it was a ‘woo.’”

According to Sharf, those around Flair were careful about how the moment played out given his age and health monitoring. ​“His team was concerned a little bit because he’s 77 years old and lived the life of a rockstar. He has a legit heart monitor on his wrist. They were concerned not to get too overwhelmed.”

The original WrestleMania 24 match between Flair and Michaels remains one of the most beloved send-offs in wrestling history, built around the storyline that Michaels would have to be the one to finally end Flair’s career. The image of Michaels reportedly gifting Flair a Rolex afterward became one of those behind-the-scenes stories that added even more weight to an already legendary night. Nearly two decades later, seeing that gesture symbolically restored speaks to how much that match still resonates with fans and with the wrestling community at large.

For Flair, who has remained a visible presence on the autograph and convention circuit in his later years, the gift is a reminder of both his enduring connection to fans and the lasting bond formed in that ring with Michaels. It’s a small story in the grand scheme of the wrestling business, but the kind that underscores why WrestleMania 24 still gets talked about all these years later.

Thank You So Much @romansharf! This Made Me Very Emotional! pic.twitter.com/3gNkguOVI5

— Ric Flair® (@RicFlairNatrBoy) July 31, 2026