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Tom Brady at “The Greatest Roast of All Time: Tom Brady” live on Netflix May 5th 2024 Sunday at the Kia Forum. pic Chris Pizzello / Invision / Associated Press


An Unexpected Visitor in 2005

In 2005, while working in luxury watch retail, I had the unexpected pleasure of assisting NFL legend Tom Brady. Fresh off his third Super Bowl win with the New England Patriots, he entered the store incognito in a grey hoodie and dark sunglasses. Recognizing his need for privacy, I quickly introduced myself and led him to a secluded upstairs area showcasing high-end watches.

I gave Tom a detailed tour, showcasing each watch brand we carried. He was cool and collected, wearing a stainless steel IWC Doppel Chronograph with a silver dial that matched his understated style. This interaction was memorable not just because of his celebrity status but also due to his humble demeanor.

Watching “The Greatest Roast of all Time:Tom Brady”

Fast forward to May 5th, 2024, when “The Greatest Roast of all Time: Tom Brady” aired live on Netflix. As someone who worked with Tom Brady and a Boston native, my curiosity was piqued, and I tuned in with no particular expectations. The event was refreshingly reminiscent of traditional roasts, where comedians spared no expense at humor without succumbing to the pressures of political correctness/woke cancel culture that has permeated much of media in recent years.

A Unique Timepiece Spotted



Tom Brady wearing a unique one of a kind AP Royal Oak Flying Tourbillon Credit: Netflix
Tom Brady’s unique one of a kind AP Royal Oak Flying Tourbillon- Credit: X/GentsPlaybook


During the roast, Tom Brady wore a striking AP Royal Oak Flying Tourbillon with a salmon dial and a baguette diamond bezel—a bold choice that perfectly suited the event’s extravagant atmosphere. This was quite a shift from the more understated style he favored when I worked with him. The dial, adorned with baguette diamonds spelling “Tom Brady” from the eight to four o’clock position and “VII” in sapphires, symbolized his seven Super Bowl victories. The Flying Tourbillon, prominently positioned at six o’clock, added a dramatic finishing touch to this remarkable timepiece.



Kevin Hart at the Greatest Roast of All Time:Tom Brady Credit:Netflix 


Audemars Piquet ROYAL OAK PERPETUAL CALENDAR OPENWORKED in black ceramic Ref. 26585CE.OO.1225CE.01


Another watch that stood out was worn by the host, Kevin Hart. More subdued and to my taste, Kevin sported an AP Royal Oak Perpetual Open Worked in Black Ceramic. Though typically not a fan of black ceramic, this watch, paired with his black outfit, resonated well with me, blending seamlessly with his style.

A ring for the GROAT


View of the “GROAT” ring Credit: JOBH IG
Front view of the “GROAT” ring Credit: JOBH IG
Left side view of the “GROAT” ring Credit: JOBH IG
Right side view of the “GROAT” ring Credit: JOBH IG


To close the show out, Kevin Hart gifted Tom Brady a championship-style ring designed by renowned jeweler Jason Arasheben, with who is a friend and I had the privilege of opening his first boutique at the Cosmopolitan Hotel in Las Vegas back in 2010. The $40,000 yellow-gold piece, adorned with a football design surrounded by a ruby flame and encircled with diamonds and sapphires, celebrated Brady as the “Greatest Roast of All Time.

At the end of the day…

The roast was a showcase for some of the hottest comics like Tony Hinchcliffe(who wore a s/s Rolex Submariner w/Date), Andrew Schulz, Bert Kreischer(who wore an Day/Date 40 in Everose),Tom Segura( who was wearing an AP Code 11:59), and Nikki Glaser. Tony stole the show with unforgettable bits, and SNL writer and fellow Bostonian Sam Jay delivered a knockout performance. At the end of the day, in my opinion, the event marked a shift in the pop cultural landscape, offering humor without the constraints of political correctness. or cancel culture.

Due to the unpredictable and volatile market on certain Rolex, Patek Philippe and Audemars Piguet watches, prices are subject to change.