Kevin O'Leary's Watches: Why Mr. Wonderful Wears Two at Once
Last updated: June 2026
Kevin O'Leary, the investor better known as "Mr. Wonderful" from Shark Tank, wears two watches at the same time on purpose: one set to New York time and one to Abu Dhabi time, because he does heavy business in the United Arab Emirates. He is not just a wealthy guy who buys watches, either. He is a member of the Horological Society of New York, sits for collector interviews, and runs his own watch content on YouTube. So when he straps on two at once, it is a deliberate choice from someone who thinks hard about what is on his wrist.
Below is what is actually documented about O'Leary's watches, pulled from his own on-camera comments and from tier-one interviews rather than guesswork. We will start with the two-watch question everyone asks, then walk through the collection he has talked about publicly.
Table of Contents
Why he wears two watches at once
In a 2024 NewsNation interview with Chris Cuomo, O'Leary held up both wrists and explained the setup plainly: "New York time and Abu Dhabi time. This is where all the money is in the world." That is the whole reason, and it is function, not theater. One zone for home, one for the Gulf, where a chunk of his business runs. It also fits a habit he has described of rotating through several watches in a day to keep them running, which we will get to. Two time zones, two wrists.
The two-watch habit has a long lineage
Wearing two watches at once sounds eccentric until you look at who else has done it, and why. The reasons usually come back to tracking two time zones at the same time. On the first American spacewalk, during NASA's Gemini 4 mission in June 1965, astronaut Ed White wore two Omega Speedmaster 105.003 chronographs, one tracking mission-elapsed time and one set to Houston time, according to NASA engineer James Ragan as told to Fratello.
During the Gulf War, General Norman Schwarzkopf reportedly wore two watches, his left wrist on Saudi time and a Seiko on his right set to Eastern Standard Time, per Watches of Espionage and aBlogtoWatch. Go back further and Fidel Castro was photographed in the 1960s wearing two Rolexes at the same time, as Quill & Pad notes. O'Leary's New York and Abu Dhabi arrangement follows the same dual-time logic, just with a banker's calendar instead of a flight plan.
The "three horsemen"
In an interview with Quill & Pad, O'Leary described what he calls his "three horsemen," the trio he reaches for most: an Audemars Piguet Royal Oak "Jumbo" in blue, a Patek Philippe Nautilus 5711/1A in blue, and a Vacheron Constantin Overseas in blue. He has said he swapped Rolex out of that top slot in favor of the Vacheron. We are not going to pin exact reference numbers on the AP or the Vacheron here, because the tier-one interviews name the models, not the catalog codes.
The Vacheron Overseas is the one that ties his whole approach together. The Overseas Dual Time, below, carries a second time zone right on the dial, which is the mechanical version of the two-handed trick he does by strapping on a second watch. It sits in the same family as one of his three horsemen, and it is one we stock.
Beyond the trinity
Robb Report, in a July 2022 profile, filled in the rest. O'Leary owns four F.P. Journe pieces, including the Chronometre a Resonance and the Centigraphe Souverain; he told the magazine that when a boutique showed him the Centigraphe, he felt it "was made for me." His first luxury watch was a 1975 Omega Speedmaster, which he still has. He owns two Rolex Daytonas, one a gold diamond piece he calls his "Eye of the Tiger." And tying right back to the dual-time theme, he has a limited Montblanc Orbis Terrarum world timer, number 18 of 71, made for the United Arab Emirates' 50th anniversary. We are leaving the exact Daytona references out, since the tier-one coverage names the watches but not the specific refs.
A collector who actually wears them
O'Leary is not a safe-queen collector. He told Quill & Pad, "I believe that the soul of a watch is kept alive by wearing it, and I often wear three different watches in a day." That is the same instinct behind the double-wristing: watches are built to run, so he runs them. He is also publicly anti-smartwatch, which fits someone with this many mechanical pieces. Between the HSNY membership, the on-camera collector interviews, and his own watch content, he is about as engaged as a public-figure collector gets. Values here vary by condition, box and papers, so treat any number as a moving target.
Sources: Quill & Pad; Robb Report (July 2022); NewsNation (Chris Cuomo interview, 2024); Fratello (NASA engineer James Ragan on Ed White's Gemini 4 Speedmasters); Watches of Espionage and aBlogtoWatch (General Schwarzkopf); Horological Society of New York membership. Secondary-market commentary reflects industry experience and is not financial advice; values vary by condition, completeness of box and papers, and seller. Watches Off 5th is an independent pre-owned and grey-market dealer.
Frequently Asked Questions
Why does Kevin O'Leary wear two watches at the same time?
He sets one to New York time and one to Abu Dhabi time for his business in the United Arab Emirates. As he put it on NewsNation, "New York time and Abu Dhabi time. This is where all the money is in the world." It also keeps both watches running. It is function, not a flex.
What watches are in Kevin O'Leary's collection?
His "three horsemen" are an AP Royal Oak Jumbo, a Patek Nautilus 5711/1A, and a Vacheron Overseas, all in blue. He also owns four F.P. Journes including the Resonance and Centigraphe, a 1975 Omega Speedmaster, two Rolex Daytonas, and a UAE-edition Montblanc world timer, per Quill & Pad and Robb Report.
Is wearing two watches a real thing or a gimmick?
It has a real traveler and military lineage. Astronaut Ed White wore two Speedmasters on Gemini 4 in 1965, General Schwarzkopf wore two in the Gulf War, and Fidel Castro was photographed in two Rolexes in the 1960s. O'Leary follows the same dual-time logic, one wrist per zone.
Is Kevin O'Leary a serious collector?
Yes. He is a member of the Horological Society of New York, sits for collector interviews, and runs his own watch content on YouTube. He is publicly anti-smartwatch, and his stated philosophy is that "the soul of a watch is kept alive by wearing it."