$1,000,000 Watch Collection Challenge with Kevin O'Leary
There are watch shopping trips. And then there is this.
I met up with Kevin O’Leary at The 1916 Company’s collector lounge in New York City with a simple idea: let’s build watch collections on camera. My original thought was a $250,000 budget.
Kevin immediately said no.
Instead, we each got $1,000,000 to spend.
What followed was one of the most entertaining watch conversations I’ve had. Kevin approached the challenge like a pure investor. Maximum diversification. No two dials alike. Big statements. Heavy hitters. I took a different route. I wanted sport watches, complications, independents, and pieces I could actually imagine wearing regularly. When you’re staring at six- and seven-figure watches, strategy starts to matter very quickly.
That mindset actually shows up in Kevin’s real-world watch choices too. While he’s known for wearing some very high-end pieces on Shark Tank, he occasionally throws something unexpected into the mix. On the March 4, 2026 episode, that watch was the Wren Diver 38 Aqua.
It’s a 38 mm diver with a vivid aqua dial, powered by a Swiss-made ETA 2892 automatic movement, with a ceramic bezel insert and sapphire caseback with a custom rotor. In other words, not a million-dollar watch. Just a well-executed, thoughtfully designed diver. If you want the same watch Mr. Wonderful wore on TV, the Diver 38 Aqua is available directly from us here.
Back to the $1,000,000 challenge.
There were surprises. There were controversial picks. And yes, there was plenty of trash talk. The best part of episodes like this is that there is no single right answer. Two collectors can walk into the same room, look at the same watches, and build completely different collections.
Watch the full video above and let me know who built the better $1 million collection.
If you’re curious about what else Kevin wears when he’s not building a fantasy $1,000,000 lineup, you can dive into our full breakdown of Kevin O’Leary’s watches and what’s in the Shark Tank star’s collection.
