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While growing up, Kevin O’Leary received many opportunities to travel since his step-father was in the United Nations and would travel for work. He spent a good portion of time in Geneva, Switzerland, where he fell in love with. Today, with a growing net worth of $400 million, the business tycoon has spent a fortune buying suitable timepieces every time he achieved success in something related to his work. O’Leary ensures that every time he is on television, he has a uniform that includes a white shirt, a black suit, and a matching tie. His watches also follow the pattern, and most of the timepieces in his collection have a red strap.
A person who believes in the brand and follows his heart rather than the trends when it comes to watchmaking, Kevin O’Leary has a masterful watch collection worth more than a few hundred thousand dollars.
F. P. Journe Elégante 48 mm Titalyt- $65,000
F. P Journe is a unique luxury watchmaking brand in the world. It is a large independent brand still run by the owner, one of the world's youngest watch manufacturers. The exclusivity of the watches makes them a good investment option for the future. O’Leary owns the Elégante 48 mm Titalyt timepiece, a watch that took eight years to develop and features a mechanical motion detector. As mentioned by F. P. Journe, the sensor helps the watch go on standby mode when it is not being used to save energy.
Patek Philippe Nautilus 5711- $100,000
Patek Philippe launched the 5711 series to commemorate Nautilus’ 30th Anniversary in 2006. The watch instantly became a sought-after timepiece, and the watch's price has only skyrocketed over time. The octagon-shaped bezel holds the black-blue dial, while the exterior is made from steel. While the Nautilus 5711 was for $30,620, it has now increased to upwards of $100,000 as the series will be discontinued after 2022, as stated by The Watch Lounge.
Jacob & Co Epic x Chronograph- $33,955
Epic x Chronograph is a bold statement piece that combines high-tech materials and traditional design. There are many models offered in the collection, and O’Leary owns the timepiece in a black titanium ceramic bezel crafted from Grade 5 titanium. Smoked sapphire glass covers the dial, and the inserts are designed in an all-black theme. The hour and minute hands are skeletonized, while the second's hand is red.
Rolex GMT-Master II ‘Pepsi’- $19,000
Nicknamed Pepsi due to its two-color red and blue ceramic bezel, the GMT-Master II, owned by O’Leary, is one of the most popular timepieces in Rolex’s collection. It is specifically designed to show two different time zones during an intercontinental flight, as noted by Rolex. The watchmaker has used innovative technology, introduced the 24-hour rotatable bezel, and finished it with a stylish ceramic bracelet.
Jaeger-LeCoultre Reverso Grande Gmt- $11,000
Jaeger-LeCoultre first introduced the Reverso Grande Gmt in 2009, and Kevin owns the timepiece in the shade of rose gold. The 18-carat rose gold watch has an art-deco classic dial, a large space to display the date, and a second dial for local time. The manually winded Reverso Grande has a power reserve indicator, and a new brown alligator leather strap with a matching rose gold clasp.
Panerai Luminor 1950 Acciaio- $8,000
One of O’Leary’s favorite watches, the Panerai Luminor 1950 Acciaio, features a circular crown guard and a cushion-shaped case. According to the Swiss Watch Expo, O’Leary switched the usual brown strap of the watch for a red one on the 45 MM timepiece. It has the Panerai signature sandwich dial between the movement and the dial’s surface, which enhances the bright background of the watch.
Cartier Roadster- $3,690
The business tycoon once owned a Cartier Panthere, one of his first watches ever; however, the watch was stolen from him. He replaced it with a Cartier Roadster, which, as the name suggests, was inspired by automobiles, specifically from the 1950s. The curves of the vintage cars inspire the tonneau-shaped case of the timepiece, and O’Leary has another watch that sports his signature red strap.
Rolex Cosmograph Daytona- $24,790
The first oyster-cased Chronograph, Rolex rolled out the first edition of the Cosmograph in 1963, nicknamed the Daytona during World War II. It remains the most iconic watch produced by Rolex and has improved its iterations over time. O’Leary owns two Daytona timepieces with black and white dials. He once again replaces the ceramic bezel of the watch with his favorite red strap.
Other notable watches in his collection include a Rolex Submariner Steel Yellow Gold Blue Dial and a Rolex Sea-Dweller with a red strap. Kevin O’Leary has created a standard for himself when collecting watches and remains true to them. He keeps his childhood fascination with watches alive by collecting the best timepieces that will remain invaluable to him.
Sources: The Watch Lounge, Rolex, Swiss Watch Expo, F. P. Journe