Mike Tyson VS Jake Paul’s Watch Collection

Nov 15, 2024

Nov 13, 2024; Irving, TX, USA; Jake Paul (right) faces off with Mike Tyson after their press conference at The Pavilion at Toyota Music Factory. / Kevin Jairaj-Imagn Images

By Robertino Altieri , CEO of WatchGuys and Harrison Minihane

As the hours count down towards the biggest fight of the year, potentially the decade, between ‘Iron’ Mike Tyson and Jake Paul, WatchGuys have taken the time to look into the watch collection of Mike Tyson and Jake Paul. Let's see who wins this round!

At 58 years of age, Tyson has one of the longest-spanning careers in the sport. He became the youngest ever heavyweight champion and now almost 40 years later he has gripped the attention of the world once more. He was one of  the highest-paid athletes ever to step into the ring, famously went broke after disputes with his former promoter Don King, and made it all back again. From tigers, to super cars, to mansions, to luxury watches - this man has had and seen it all.

His opponent, Jake Paul has reached superstar-level status. From YouTuber to Pro Boxer, who will win the fight? As the first bell approaches, we’ve handpicked our favorites from WatchGuys in the spectacular watch collection of two of the world’s most fascinating entertainers.

Mike Tyson’s Watch Collection

Piaget Pave Diamond Jewelry Watch

Will this timepiece an appearance at the Tyson vs. Jake Paul main event on November 15? / Robertino Altieri, CEO of WatchGuys.

Estimated Value: $100,000+

This piece is more than just a watch; it’s a testament to Tyson’s larger-than-life persona and one of the most infamous, yet controversial moments in watch history—because Tyson essentially "walked off" with it from the Piaget boutique.

As the story goes, when Mike Tyson was at the height of his fame as one of the biggest names in sports, he walked into a Piaget boutique, spotted the watch, and put it on his wrist. Looking the sales clerk straight in the eyes, he declared, “Showtime will pay for it,” and walked right out.

Afterward, despite repeated demands from Showtime's agents and lawyers to return the watch, Tyson refused. He even threatened to pull out of an upcoming fight—a fight too valuable for Showtime to lose. Cornered, Showtime eventually paid the hefty price tag. Ever since, Tyson has made this timepiece his signature, wearing it to nearly every major fight.

Will it make an appearance at the Tyson vs. Jake Paul main event on November 15th? The watch world certainly hopes so.

Yellow Gold Cartier Pasha Chronograph

Estimated Value: $15,000

Tyson’s yellow gold Cartier Pasha Chronograph is a classic piece with a unique twist—a 38mm case that’s smaller than today’s favored 40/41mm size but perfectly suited to Tyson’s taste. This watch stands out for its black chronograph subdials, adding contrast to the gold, making it a distinctive piece in his collection.

Tyson’s appreciation for the Pasha knows no bounds, as he also possessed a stainless steel variant with a leather strap / Robertino Altieri, CEO WatchGuys.

Tyson was often seen wearing this Pasha during his early days, including in an iconic photo with his manager Don King. Rumor has it that Tyson, as a gesture of loyalty, later gifted this watch to King. Tyson’s love for the Pasha extended further, as he also owned another version in stainless steel with a leather strap, revealing his appreciation for Cartier’s blend of elegance and bold design. Today, the watch is valued at around $15,000, but as a piece of Tyson’s history, it carries a legacy far beyond its market worth.

Rolex Day-Date 18038

Tyson’s selection of this slightly smaller size demonstrates his reverence for the true classic, aligning him with other renowned enthusiasts, including Tony Soprano / Robertino Altieri, CEO WatchGuys.

Estimated Value: $15,000

The Rolex Day-Date 18038 is the classic yellow gold “President” that many picture when they think of this iconic model. While Tyson’s presence might seem suited to a larger 40mm watch, the 36mm Day-Date is the quintessential size, embodying elegance without needing oversized flair. Tyson’s choice of this slightly smaller size shows his respect for the true classic, joining the ranks of many other famous Day-Date wearers, like Tony Soprano. For me, this is the standout piece from his President collection.

Interestingly, Tyson’s taste for refined sizing doesn’t stop there. He’s also been seen wearing a 34mm Rolex Oyster Perpetual—a surprisingly understated choice for “Iron Mike” and one that reflects his unique sense of style. And for moments where he wants to add a bit of extra flash, he turns to his diamond-encrusted Day-Date 18048, complete with a diamond bezel and dial. This piece brings Tyson’s collection to the next level, blending classic elegance with just enough sparkle to remind everyone who’s wearing it.

In Tyson’s collection, the Day-Date series perfectly bridges his powerful image with a touch of timeless style, whether he’s keeping it classic with the 18038 or dialing up the luxury with the 18048.

Jake Paul’s Watch Collection:

While Mike Tyson’s watch collection reflects timeless style and classic flair, Jake Paul’s lineup is all about modern luxury and making bold statements. Known for his larger-than-life personality, Paul’s watches are as extravagant and high-profile as he is. His collection showcases some of today’s most coveted, high-end pieces, including brands like Richard Mille, Jacob & Co., and MB&F, each chosen to capture attention both in and out of the ring.

Today, we’re taking a closer look at three of my favorite Jake Paul pieces:

Jacob & Co. Billionaire Watch

Estimated Value: $7,000,000+

Estimated at a staggering $7 million, Paul was spotted just days before the fight sporting this jaw-dropping full diamond watch in what appeared to be his home and again at the press conference. With over 300 Ashoka-cut diamonds set in 18k white gold, this watch is nothing short of a spectacle. Known for his eye-catching style, Paul announced he’ll be wearing a $1 million outfit for the fight on November 15. He’s promised “the most expensive fight outfit in the history of boxing” and hinted he’ll be arriving in a special vehicle for his ring walk. We’re all eager to see how he’ll up the ante on fight night with this insane watch on his wrist.

Adorned with over 300 Ashoka-cut diamonds and crafted from 18k white gold, this watch is truly a breathtaking masterpiece / Robertino Altieri, CEO of WatchGuys.

Jacob & Co. Bugatti Chiron Tourbillon

Estimated Value: Over $300,000

Inspired by the legendary Bugatti Chiron supercar, this watch seamlessly merges automotive design with luxury watchmaking craftsmanship / Robertino Altieri, CEO of WatchGuys.

In November 2022, during his pre-fight event with Anderson Silva, Paul rode in on a horse to their open workout, all while sporting his new Rose Gold Jacob & Co. Bugatti Chiron Tourbillon. This watch, inspired by the iconic Bugatti Chiron supercar, brings automotive design into luxury watchmaking. Its case fuses glass and metal, reflecting the Chiron’s horseshoe grille, powerful body, and headlights, while a sapphire panel reveals a movement reminiscent of Bugatti’s W16 engine block. Complete with a power reserve mimicking a fuel gauge and a radiator-like tourbillon carriage, this watch channels the thrill and high performance of the Bugatti, blending it into a timepiece that’s as audacious as Paul himself.

Rolex Oyster Perpetual 124300 (Tiffany Blue Dial)

Estimated Value: $30,000

The Rolex Oyster Perpetual 124300 stands out as a beacon of class and elegance in Paul’s impressive collection / Robertino Altieri, CEO of WatchGuys.

Among Paul’s show-stopping collection, the Rolex Oyster Perpetual 124300 is a classy standout. The OP 41 in Tiffany Blue has become highly sought after since Rolex discontinued the color, making it an instant classic. I’m personally a fan of this model; in fact, I own a rare 2020 version, fully stickered and new old stock. The average price for the Tiffany OP 41 sits around $30,000.

WatchGuys are one of America’s leading online buyers and sellers of pre-owned Rolex Watches, located in the heart of Los Angeles’ Jewelry District. They take pride in offering some of the finest selection of timepieces in the world.