I have been a fan of ABC’s Shark Tank ever since it premiered in 2009. Anyone that has a little bit of that entrepreneurial spirit will enjoy average Joe’s pitching their ideas to the Sharks. It was pretty early that I noticed that many of the Sharks had some pretty nice timepieces. Daymond John, the founder of FUBU, always wore unique and large timepieces, which I have not always been able to successfully identify. Robert Herjavec, the founder of the Herjavec Group, always had nice timepieces, including some very nice gold Rolex Daytonas.

And then there is Kevin O'Leary. The self-described “Mr. Wonderful” is a sharply dressed multi-millionaire (his net worth is estimated at about $400 million USD) who is always wearing a black suit, pin-collared button down shirt, and high-end timepiece. I must admit though, I was not initially impressed with O’Leary’s watch knowledge. As an aside, one of the first time I realized he was interested in watches was when I watching in a December 2018 episode of the show. O’Leary was hearing pitches and went off on one of his well known tangents. “Listen Santa” he said (it was a Christmas episode) “I collect watches. There is a watch called the Patek Philippe 7511 blue face. It’s incredibly rare. I’m deserving of one, and I’ve been incredibly good this year.” We all know that the watch is actually a 5711 and it is incredibly, incredibly rare (even more so than back in 2018). But you would expect a true watch collector to get the reference of such an important classic watch right. However, I’ll give him the benefit of the doubt for the gaffe though. I will admit that it was fun to see him botch the classic Nautilus’ reference on national television.

So what watches does Kevin O’Leary wear? It turns out he has quite the collection. He also spends quite some time discussing watches on his YouTube channel. Let’s take a look at a few of his timepieces.

Kevin O’Leary’s Patek Philippe Nautilus 5711

I guess Santa eventually gave in and gave little Kevin that Patek Philippe Nautilus after all. Apparently it only took Santa a year to get Kevin that coveted blue dial Nautilus. He was spotted wearing one in February of 2019. While the now discontinued watch at the time retailed for under $30,000 USD, it is now selling on the secondary market for over $140,000 USD. We know Mr. Wonderful likes a return on investment, and it appears that he will get it with this piece. Here’s my pitch for a new Shark Tank spin-off: Kevin O’Leary Watch Investments. Anyway, moving on.

Kevin O’Leary’s Rolex Daytona 116500

It may be just me, but I think everyone who collects Rolex should have a stainless steel Daytona in their collection (I personally have a 116520 that I’ve owned since 2013). Well, it appears that Kevin O’Leary agrees. He has been seen wearing the new steel Rolex Daytona with ceramic bezel Ref. 116500. This is the very same watch I put my name on the waitlist for before it was released (and before I knew any better) and never heard back (I’m still waiting…). This classic beauty retails for $14,550 USD (yay Rolex 2022 price increases!) but will set you back $36,000 USD plus on the grey market.

It turns out that O’Leary sold his Daytona at auction with Phillips back in 2019. The final price was $56,700 USD. O’Leary donated the watch to benefit the missions of One Drop and the Prince Albert II of Monaco Foundation.

Kevin O’Leary’s Rolex Daytona 116500 — The photo on the right is of O’Leary’s actual Rolex Daytona. Photo courtesy of Phillips Auctions.

Kevin O’Leary’s Rolex Daytona “Eye of the Tiger”

If you watched Shark Tank on January 28, 2022, you will have noticed that O’Leary was once again wearing a watch he hasn’t been seen in. The watch he was wearing is the gold Daytona Ref. 116588TBR “Eye of the Tiger”. Rolex is known to make only a few really blinged out pieces, one of them being the Daytona Rainbow Ref. 116595RBOW, and the other being the Daytona “Eye of the Tiger.” The Daytona “Eye of the Tiger” is not for everyone, with its diamond-set bezel and diamond-encrusted tiger-stripe pattern dial. But if it is your cup of tea, you can purchase one on the secondary market for north of $200,000 USD. Obviously Mr. Wonderful’s piece is on his signature red strap.

Kevin O’Leary’s Rolex GMT-Master II Pepsi

After browsing through some photos of Mr. Wonderful, I noticed he was wearing a watch that hasn’t been spotted before on his wrist. While appearing on Mornings with Maria, O’Leary can be seen wearing a steel Rolex GMT-Master II on his signature red strap. This watch retails for $10,750 USD on jubilee (this photo was taken in 2019 before the oyster version was released) and sells for above $30,000 USD on the secondary market.

Kevin O’Leary’s Jacob & Co. Epic X Chronograph

Who knew that Kevin O’Leary had something in common with Conor McGregor. Well, not really, but both O’Leary and McGregor have a Jacob & Co. Epic X Chronograph in their collection. O’Leary has a black titanium model with red strap. The retail price on this Jacob & Co. piece is $24,000 USD.

Kevin O’Leary’s Jaeger-LeCoultre Reverso Grande GMT

Kevin O’Leary is no Bruce Wayne, but the two do share their love for the classic Jaeger LeCoultre Reverso Grande GMT in rose gold (Bruce Wayne’s was actually in steel). What makes the Jaeger LeCoultre Reverso so unique is that the case can be flipped over and locked in place to show only the caseback with engravings and serial, hiding the dial. While the retail price on this piece is $28,400 USD, you can actually buy it on the secondary market for a significant discount at around $17,000 USD.

Photo courtesy @kevinolearytv on Twitter.

Kevin O’Leary’s Panerai Luminor Base Destro Ref. PAM 219

It seems O’Leary is a fan of red straps on his watches (his Daytona and Epic X have both been mounted on red straps). Well, his Panerai Luminor Base Destro Ref. PAM 219 44mm is also on a red strap. This piece is one of the more basic Panerai models and currently is available on the secondary market for between $5,000 and $6,000 USD. Interestingly, while O’Leary is not left-handed, this watch is considered a left-handed watch with the crown on the left side of the case.

Kevin O’Leary’s F.P. Journe Élégante 48 mm Titalyt

Forgive me Mr. O’Leary for doubting your watch collecting knowledge. Anyone who has an F.P. Journe in their collection must know at least a thing or two about watches (Nautilus gaffes aside). For those who don’t know F.P. Journe, it is a Swiss independent watch brand, that happens to be the only three-time winner of the Aiguille d'Or grand prize from the Fondation du Grand Prix d'Horlogerie de Genève. The company’s motto of Invenit et Fecit (Latin for "He invented it and made it") denotes the fact that their movements are completely designed and manufactured in-house. Indeed, F.P. Journe watches remain some of the most coveted watches on the market. Kevin O’Leary’s F.P. Journe Elegante 48 MM Titalyt is also on red strap. His watch has a titanium case with a luminescent sapphire dial quartz electromechanical, patented two-rotor motor movement. While the retail price of this piece is under $14,000 USD, the current market price is over $60,000 USD.

Kevin O’Leary’s Audemars Piguet Royal Oak Jumbo Ultra Thin 15202

If anyone caught Shark Tank on January 21st, 2022, you definitely caught Kevin O’Leary wearing a shiny new watch (on his signature red rubber strap). So what watch was Kevin O’Leary watching on the Shark Tank Season 13, Episode 12? He was wearing perhaps the most highly sought after Audemars Piguet, the AP Royal Oak Jumbo Ultra Thin Ref. 15202 with blue dial. You can tell that it is this piece and not the 15500 because of the thin profile, shape of the lugs and the AP marking at 6 o’clock. This Audemars Piguet Royal Oak Jumbo Ultra Thin retails for $33,200 USD but is currently selling on the secondary market for anywhere from $100,000 USD to $140,000 USD depending on the age and condition.

Kevin O’Leary’s 1 of 1 Audemars Piguet Openworked with Ruby-Set Bezel

If you have been following O’Leary in early 2023, you’d know that he has taken his watch collecting up a notch. He recently posted a couple of Instagram reels showcasing his new one of one piece unique Audemars Piguet Royal Oak. This piece has an openworked dial and the bezel is set with rubies. Beyond that, we don’t know much about this watch (besides it is the only one in the world). We would assume the case is either white gold or platinum, but it could be steel. And yes, Kevin has it on his signature red (gator) strap.

Kevin O'Leary's Watches - What is in the Shark Tank Star's Watch Collection?