Tom Brady’s Collection of Outrageous Rolex Watches Keeps Growing

The insane horological journey of Tom Brady continues apace with the spotting of yet another standout, gem-set Rolex.

Spotted this week at the Cardinals vs. 49ers game, Brady rocked the Rolex Cosmograph Daytona ref. 116578SACO, an 18K yellow-gold version of the Crown’s famed racing watch in an unusual configuration. The bezel is set not with diamonds, but with 36 cognac-colored sapphires, while the dial is mother-of-pearl with diamond-set indices. Brady’s model is only slightly less ostentatious than its predecessor, the ref. 116598SACO “Leopard” Daytona from 2004, though not by much. These colorful Cosmograph are certainly an acquired taste but have become one of the most desirable subsections of the Crown’s catalog.

Like many of Brady’s watches, this Daytona is a rarity, with secondary-market pricing hovering at well over a quarter-million bucks. As far as gem-set Rollies go, it might not have the cachet of a “Rainbow” Daytona—those whose bezels are set with a selection of sapphires in a rainbow-hued configuration—but people go absolutely bananas for these sorts of Daytonas in general.

The ref. 116578SACO is far from the only standout Rolex in Brady’s collection: There’s a “John Player Special” ref. 6241 from the 1960s in yellow gold that’s probably worth a couple-million bucks; there’s a platinum Day-Date with an Arabic dial for the Middle Eastern market that he wore to the French Open last year; the new grey-and-black GMT-Master II that he rocked at the Olympics; a “puzzle-dial-emoji” Day-Date that lit up the internet in 2023; and a whole bunch of other stuff too numerous to elucidate here.

Steve Harvey’s Richard Mille RM 65-01

Steve Harvey’s latest bit of horological fire? The Richard Mille RM 65-01, spotted on his wrist while sitting courtside at an NBA game in Abu Dhabi. The RM 65-01, a split-seconds chronograph with all sorts of bells and whistles, comes in several configurations, but Harvey’s was only introduced this year and distinguishes itself with its yellow and blue quartz TPT case and wildly colorful dial. The model also features a high-frequency movement operating at 5Hz, meaning it can time down to 1/10th of a second. Harvey’s burgeoning watch collection has coincided with his overall style glow-up.

Shaboozey’s Chopard L.U.C Heritage Grand Cru

Singer Shaboozey chose a cool, left-of-center watch to pair with black tie for the 2024 Time100 Next ceremony last week. His L.U.C Heritage Grand Cru, housed in a white gold tonneau case, has a bezel set with neatly three carats’ worth of diamonds and a black bezel with silvered Roman numerals, a chemin de fer minute track, sub-seconds, a date window, and a set of syringe hands. The watch certainly has some Tank-like inspiration, but much like Shaboozey’s spin on J-Kwon’s Tipsy, largely stands on its own as a more modern take on a classic.

Jaylen Brown’s Patek Philippe Annual Calendar ref. 5235R

Also in attendance at the 2024 Time100 Next ceremony was Jaylen Brown rocking a heck of a Patek, the Annual Calendar ref. 5235R. Patek Philippe famously patented the annual calendar—a simplified take on perpetual calendar—in the 1990s, subsequently turning it into a collection of incredible watches that account for each month of the year (except for February) without the need for manual adjustment. The ref. 5235 is particularly novel for its configuration: It’s set up a “regulator” display, with the hours in a subdial at 12 o’clock; the seconds in a subdial at 6 o’clock; and the minutes indicated via a central hand. Days, months, and the date, meanwhile, are indicated via small apertures.

Michael Jordan’s Rolex Cosmograph Daytona

What’s the only thing more desirable than a yellow-gold Daytona with a cognac sapphire-set bezel and a mother-of-pearl dial with diamond indices? How about the 2023 “Le Mans” Daytona in white gold with vintage-inspired details that recall models from the ‘60s and ‘70s? Michael Jordan was one of the lucky few to secure an allocation of the ref. 126529LN, which celebrated 100 years of the 24 Hours of Le Mans and quickly exited the Rolex catalog after less than a year. It was replaced by a yellow-gold version that hasn’t been seen around much— except on the wrist of Roger Federer, Rolex testimonee extraordinaire and perennial wearer of beautiful Rollies.