"Competition was fierce" — Shark Tank's Kevin O'Leary wins a rare Chanel watch at a Phillips Auction

Shark Tank star Kevin O'Leary has added another trophy to his already impressive watch collection. The businessman recently won a one-of-a-kind Chanel Boy.Friend watch at a Phillips Auction in Singapore, paying $222,000 for the privilege. The proceeds go to charity. O'Leary announced on Instagram:

"Here it is — the Chanel 'Boy.Friend,' a watch so rare it brought grown collectors to tears."

He further wrote:

"I won this one-of-a-kind piece at the Phillips Auction in Singapore for $222,000, all for charity. Let me tell you, the competition was fierce, but no one messes with Mr. Wonderful. This design is pure art — Roy Lichtenstein vibes with a timeless edge. There's only one, and it's mine. Why? Because it looks fabulous on me, and as always, I deserve it."

Known for his sharp business acumen and even sharper instincts on Shark Tank, the Canadian television personality and investor has established a solid reputation as a devoted watch collector. Some of the most coveted timepieces in the world, such as rare pieces from Patek Philippe and Rolex, are part of his collection, frequently adorned with his signature red straps.

Kevin O'Leary fights fiercely for the Boy.Friend

Kevin O'Leary isn't just another wealthy investor with expensive taste. Since 2009, he's been a fixture on Shark Tank, where his direct approach and memorable one-liners have earned him the nickname "Mr. Wonderful." Beyond the television screen, O'Leary is known for his impeccable style — always appearing in tailored suits, trademark red ties, and carefully chosen timepieces.

The Phillips Auction in Singapore turned into quite the spectacle, according to O'Leary's account to Fox Business. O'Leary said about his main competitor at the auction:

"He would not stop. He would not stop, but he was messing with Mr. Wonderful. That's important to know."

The Chanel Boy.Friend watch is more than just another addition to O'Leary's collection. Its unique design, which O'Leary compares to Roy Lichtenstein's work, sets it apart from his other timepieces. The fact that it's a one-of-a-kind piece makes it particularly special in a collection that already includes numerous rare watches.

Kevin O'Leary’s ever-growing collection of watches

O'Leary's watch collection reads like a who's who of luxury timepieces. His vault includes the highly coveted Rolex Daytona 'Panda' 116500LN, valued at around $35,000, and the more extravagant Rolex Daytona 'Eye of the Tiger' 116588TBR, which commands over $200,000 in the market.

Perhaps the most striking piece in his collection before the Chanel acquisition was the Patek Philippe Aquanaut Luce Rainbow. Despite being designed for women, the $500,000 timepiece has found its way onto the wrists of several male celebrities, including Kevin O'Leary.

This latest acquisition cements O'Leary's status in the watch-collecting world. His collection now spans from the business-like Rolex GMT-Master II Pepsi to the avant-garde Jacob & Co. Epic X Chronograph, and includes the respected independent watchmaker F.P. Journe's Élégante 48 mm Titalyt.

What makes Kevin O'Leary's collection unique isn't just the valuable timepieces, but his personal touch. He's known for switching out original straps for red rubber ones, creating a signature look that matches his bold personality.

The addition of the Chanel Boy.Friend watch, with its artistic design and charitable connection, adds a new dimension to O'Leary's collection.

"Amongst watch collectors around the world, grown men are weeping about this piece. This is absolute madness,"

he said, while proudly displayed the watch on live television.