Sports

Kevin O’Leary Wears $30 Million Kobe, LeBron, Jordan Triple Logoman Necklace at the Oscars

O'Leary paired a seven-month-in-the-making Dolce & Gabbana jacket with the historic NBA collectible set in a bespoke diamond necklace.

Kevin O'Leary in a black and silver ornate suit poses with open arms in front of an Oscars backdrop.
(Photo by Gilbert Flores/Penske Media via Getty Images)

Kevin O'Leary turned heads on the Academy Awards red carpet with a piece of jewelry that doubles as one of the most valuable sports collectibles in the world.

The businessman and television personality, who also appears in the upcoming film Marty Supreme, arrived wearing a custom necklace built around the legendary Triple Logoman card, a rare collectible featuring game-worn patches from three NBA icons: Michael Jordan, Kobe Bryant, and LeBron James.

The piece is estimated to be worth somewhere between $25 million and $30 million, making it one of the most expensive items ever worn on a red carpet. O'Leary teased the look earlier in the day with a "get ready with me" video on Instagram while preparing for the ceremony.

"Doing a final fitting ahead of the Oscars," he wrote.

According to O'Leary, the outfit itself took months to create. His embroidered black Dolce & Gabbana jacket reportedly took seven months to complete. But the centerpiece of the look was the necklace, which was custom-made by Tiffany & Co.. The design features white gold, diamonds, and carefully matched rubies surrounding the historic card.

Inside the frame sits the first-ever Triple Logoman card, which contains pieces of the iconic NBA logo patches taken from jerseys worn by Jordan, Bryant, and James during games. The collectible holds additional prestige because it is also the only PSA 10 graded Exquisite Logoman card known to exist, making it a one-of-a-kind item in the sports memorabilia world.

The Oscars appearance follows another headline-grabbing red carpet moment earlier this month when O'Leary attended the Screen Actors Guild Awards wearing a signed Jordan and Bryant card reportedly valued at around $20 million.

Related Stories

HOLLYWOOD, CALIFORNIA - MARCH 15: Timothée Chalamet attends the 98th Oscars at Dolby Theatre on March 15, 2026 in Hollywood, California.
pop-culture

Why Timothee Chalamet's Ballet and Opera Comments Likely Won't Affect His Odds of Winning an Oscar

The 'Marty Supreme' actor was in the running for Best Actor long before his comments on ballet and opera went viral.

Julian Hamilton/Getty Images /  ANGELA WEISS / AFP via Getty Images
pop-culture

Conan O’Brien Roasts Timothée Chalamet at Oscars, Jokes Tight Security Because of Ballet Remarks

The couple appeared unfazed as the late-night host poked fun at Chalamet’s recent comments about ballet and opera.

A close-up of a golden Oscar statuette, symbolizing the prestigious film award, with a blurred background.
pop-culture

Oscars 2026 Winners: 'Sinners,' 'One Battle After Another,' and More

'Sinners' is the most-nominated of this year's titles, setting a new Academy record.

Stay ahead on Exclusives

Download the Complex App