The GOAT is selling off 27 of his most cherished timepieces, including an ultra-rare Rolex and the IWC he wore during the 2021 Super Bowl victory parade.

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Tom Brady has cemented himself as one of our greatest living watch collectors. Even during his time as an IWC ambassador, he seemed to understand better than most collectors why watches matter. And since being freed from those contractual obligations last year, he’s shown off a massive range of pieces, from the buzzy Cartier Crash to an ultra-rare Rolex Daytona to a swanky Patek Philippe. Now, for the first time ever, Brady is auctioning off a selection of his watches through Sotheby’s in December.

What Brady has always understood about timepieces is their ability to capture a moment. A great watch absorbs the flavor of the emotions that come with life-changing events—the tofu of the collectibles space, if you will. “I’ve been so fortunate to have such an amazing journey in my career, and these watches and collectibles really capture those unforgettable moments and all the hard work behind them,” Brady said in a statement. “I’m excited to give fans and collectors a chance to own and cherish these special pieces from my journey just like I have.”

Brady, a seven-time Super Bowl winner, is not short on stories and accomplishments to infuse with his watches. Take for instance his IWC Pilot’s Watch TOP GUN Edition, the piece with the lowest estimate ($12,000 to 18,000) in the auction. This is the very watch that Brady wore while celebrating the parade for his 2021 Super Bowl victory. More importantly, this is also the watch that Drunk Brady wore, which is maybe my all-time favorite iteration of the GOAT. (As a New York Giants fan, my real favorite is Super Bowl runner-up Brady.)

These watches are part of a larger themed auction titled “The GOAT Collection: Watches and Treasures from Tom Brady.” In addition to watches, Sotheby’s is also bringing the Michigan jersey Brady wore during his very last game for the Wolverines, the shirt he sported during his (uninspiring) 40-yard dash at the combine, and another kind of wristwear in the form of a wristband from the New England Patriots’ legendary comeback against the Atlanta Falcons in Super Bowl LI. (Brady’s stuff does numbers at auction: Pats owner Robert Kraft recently paid $120,000 for a signed rookie card of his.) Sotheby’s plans to bring highlights from this auction to its houses in Los Angeles, Miami, and Dallas. Stay tuned for dates.

And while game-worn jerseys are cool, this auction is really about the watches. “In the past few years that I have come to know Tom Brady, watches have been our common denominator,” Richard Lopez, Sotheby’s senior specialist for watches, said in a statement. “Just as he mastered the language of football, he has devoted himself to understanding the intricacies of watches, curating a world-class assortment of exquisite timepieces in recent years that reflects his deep passion for collecting.”

Given Brady’s past comments on the subject, it’s frankly a surprise to see any of these watches come up for sale. “Hopefully I don’t sell them, which I don’t think I ever will,” he told me in 2020, after I pointed out that his timepieces will have great provenance if he ever decided to move them. “These will be hopefully in my collection for a long time.” People change!

Let’s take a closer look at each of the five watches announced so far.

Update, 2 p.m.: Sotheby’s shared there will be another 22 of Brady’s watches included in the auction. We will further update this story with those details as we receive them.

Custom Audemars Piguet Royal Oak (Estimate: $400,000 to 800,000)

This is an absolutely ridiculous watch and probably the flashiest piece in Brady’s collection: A Royal Oak made of white gold with a diamond-set bezel. The tourbillon and salmon dial already make this piece special, before you even get to the fact Brady’s name is written out—along with the Roman numeral VII—in even more diamonds on the dial. Flip the watch over, and you’ll find even more special details: The rotor (the mechanism that spins and winds the watch) is etched with Brady’s signature. The QB also happened to wear this watch during his recent smash-hit Netflix roast. So what’s the high estimate for a one-of-one, diamond-encrusted AP Royal Oak? A cool $800,000.

Patek Philippe Nautilus ref. 5980/1R-001 (Estimate: $180,000 to 240,000)

This Patek has been lurking in Brady’s collection since 2017, according to Sotheby’s. That means Brady picked this up during his time as an IWC ambassador—he wouldn’t have been able to wear it publicly at the time, but was wise to make a good investment while he could. This particular reference, the 5980/1R-001, was discontinued earlier this year. The Nautilus is one of the most coveted watches on the planet, and when you add in this version’s rose-gold case, chronograph function, and the fact that Patek no longer makes it, you have a very desirable piece.

A Rolex Day-Date reference 228396TBR (Estimate: $80,000 to $120,000)

Since retiring, Brady has proven to be a massive fan of the Day-Date. He owns two with Arabic dials, in green and icy blue, as well as 2023’s fun-loving “Jigsaw” model. This version of Rolex’s iconic dress model is just as sexy and luxurious, with a meteorite dial and diamonds set on the bezel and hour markers.

A Richard Mille 35-03 ‘Baby Nadal’ (Estimate: $300,000 to $500,000)

Brady loves Richard Mille watches inspired by other sports figures. Earlier this year, he wore the RM 11-04 made in collaboration with Roberto Mancinci, former manager of the Italian national football team. The auction, meanwhile, features Brady’s RM 035, which was produced in partnership with the brand’s longtime ambassador Rafael Nadal.

IWC’s Pilot’s Watch TOP GUN Edition ‘SFTI’ model (Estimate: $12,000 to 18,000)

The aforementioned IWC carries the most potent provenance of the bunch. This watch was worn by Brady during the 2021 Super Bowl victory parade and is the only nod in the auction to Brady’s long partnership with IWC.