This shouldn’t be surprising, given Brady’s substantial wealth. Forbes reports that during his 23-year NFL career, Brady accumulated a staggering US$530 million, with US$333 million coming from playing contracts and over US$200 million from off-field endeavours, including endorsements and business ventures.

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Here’s a look at some of the most remarkable pieces in Tom Brady’s opulent watch collection.

A seven-figure, skull-themed Richard Mille

For the eagerly awaited Rose Bowl game between Alabama and Michigan on New Year’s Day, Brady proudly showcased his Richard Mille skull-themed watch on his Instagram Story.

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Rolex Daytona “John Player Special”

Nicknamed the “John Player Special”, this ultra-rare timepiece boasts a distinctive black and gold dial designed to reflect the colour scheme of the 1970s Lotus F1 racing team. Sponsored by John Player & Sons, a cigarette company, the watch’s theme is complemented by three subdials with square lollipop markers, capturing the essence of that era’s racing heritage.

Brady’s version, which he wore to a New England Patriots halftime event honouring him, per Yahoo! Sports, is as inimitable as the star quarterback himself. With only about 3,000 units produced in the 1960s, it fetches a correspondingly high price. In fact, one of these watches was sold at auction for US$1.5 million, ranking it among the most expensive watches ever auctioned in the UK, per Hypebeast.

Rolex Day-Date Platinum with olive green face and Arabic numerals

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IWC Portugieser Tourbillon Hand Wound Squelette

As a former ambassador for IWC, Brady boasts several high-end timepieces from the Swiss watchmaker, including the Pilot’s Watch Timezoner “The Longest Flight” and Big Pilot’s Watch Top Gun Edition “Mojave Desert”.

However, his most stand-out piece is his IWC Portuguese Hand-Wound Tourbillon Squelette, worn last February, per Hodinkee. This watch features a 43mm case in 18-karat red gold, a fully skeletonised dial and movement, and a prominently displayed tourbillon at 9 o’clock. Limited to just 25 pieces, it’s yet another remarkably rare watch in his collection.

Rolex Day-Date 36 “Puzzle Dial”

Brady was one of the first to snag this special version of this beloved Rolex, per GQ, featuring a jigsaw puzzle motif on its dial, hour markers made of baguette-cut sapphires in six colours, and an aperture at 12 o’clock showcasing various inspirational words, like “hope” and “love”. Additionally, 31 different emojis rotate in the window at 3 o’clock.

This whimsical watch shows Brady’s eclectic, diverse taste as a collector, and proves that he has his finger on the pulse of what’s trending.

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Patek Philippe ref. 2499J

The iconic quarterback showcased an exceptionally rare Patek Philippe on Instagram in September, per Robb Report. This ref. 2499 is revered as a “holy grail” among watch enthusiasts – and deservedly so. With only about 349 pieces produced over its 35-year production span, this vintage gem regularly commands multimillion-dollar prices at auctions, reflecting Brady’s significant investment in his growing collection.