Watch Paparazzi

Entrepreneur Kevin O'Leary spotted wearing Rolex

Kevin O'Leary was recently spotted wearing one of the most audacious watches in the Rolex catalogue — the Daytona 'Eye of the Tiger' Ref. 116588TBR — a piece that demands attention in any room, boardroom or television set included.

The Rolex Daytona Ref. 116588TBR is built on the marque's workhorse Calibre 4130 automatic chronograph movement, a column-wheel mechanism with a vertical clutch that Rolex developed entirely in-house and introduced in 2000. It offers a 72-hour power reserve and COSC-certified chronometer accuracy. The case measures 40mm in 18k yellow gold, and the bezel is fully pavé-set with brilliant-cut diamonds. The defining feature, however, is the dial: baguette-cut diamonds are arranged in a tiger-stripe pattern across the subdials and chapter ring, requiring extraordinarily precise gem-setting work that places this squarely in Rolex's high-jewellery tier.

The reference was introduced as part of Rolex's broader push into gem-set complications, sitting alongside the now-iconic Rainbow Daytona Ref. 116595RBOW. Where the Rainbow opts for spectral sapphires on the bezel, the 'Eye of the Tiger' commits entirely to diamonds and yellow gold, producing a warmer, more singular aesthetic. Production numbers are deliberately limited, and the watch has never been easy to source even at authorised dealers — a rarity that has only compounded its desirability among serious collectors.

O'Leary has long cultivated a reputation as a committed watch collector, regularly appearing with significant pieces on Shark Tank and in media appearances. His choice of the 116588TBR is consistent with his broader collecting philosophy: high-complication, high-visibility pieces that function as wearable statements of financial confidence. The 'Eye of the Tiger' nickname suits his public persona almost too neatly.

On the secondary market, the Rolex Daytona Ref. 116588TBR commands prices well north of $200,000 USD, a substantial premium over its already considerable retail price. Demand consistently outpaces supply, and the combination of gem-set craftsmanship, Daytona provenance, and extreme scarcity ensures the reference retains strong collector interest. For those with the means and the disposition, it remains one of the most singular Daytonas money can buy.