Kevin O’Leary Turns Heads With Striking Accessory At Actor Awards

Canadian entrepreneur and TV personality Kevin O'Leary made headlines at the SAG Actor Awards, turning heads with an unexpected accessory. The bold choice served as a tribute to a late basketball legend, adding personal meaning to his daring sense of style.

O'Leary attended the 2026 Actor Awards in Los Angeles as part of the "Marty Supreme" cast, and he brought glitz and glamor to the event. He donned a black, sequined blazer over trousers, but what caught the attention of attendees was his necklace.

Hanging on O'Leary's neck was a Michael Jordan-Kobe Bryant basketball card fashioned into a necklace. Moreover, the card was signed by the two basketball legends, increasing its value. According to reports, the businessman said his accessory was worth $19.2 million.

Before the event, O'Leary posted a video on social media, explaining his unusual accessory. He was at Tiffany's on Rodeo Drive, where the card was transformed into a necklace. Per the caption, the necklace features an impressive 101 carats of diamonds and 10 carats of rubies set in white gold.

"The weight of this thing is over two pounds of solid gold and diamonds," O'Leary said before kissing the accessory.

On the red carpet, O'Leary talked to several reporters about his fashion statement, and as he told Page Six, his basketball card necklace is a great investment. "I'm looking at this card at the same way as if you could have bought a Picasso in 1962," adding that the card has "done better than crypto."

Moreover, the entrepreneur-turned-actor wanted to honor the late Kobe Bryant. "I brought this back because I want to bring Kobe back to LA on such a big night in the city," adding that it's the first time he brought the basketball card out since his purchase.

The former Los Angeles Lakers shooting guard passed away in a helicopter crash in January 2020. Among those who perished in the accident was Bryant's 13-year-old daughter, Gianna.

In August 2025, O'Leary purchased the one-of-a-kind basketball card for nearly $13 million together with two other investors. Owning the card was a dream come true for the businessman, who said that he had his eyes on the rare card for some years. It's another addition to his growing collection of basketball cards.

In an interview with CNBC, O'Leary compared the purchase to his cryptocurrency and commodity investments, saying, "It's going to be a part of an index that I'm going to continue to grow along with my partners. We look at it no different than our bitcoin holdings, our ethereum holdings, our gold holdings."

O'Leary said that purchases like the basketball card continue to appreciate, which is why it's a good investment. As for whether the Upper Deck Exquisite Collection Dual Logoman card will return to the market, O'Leary said it won't happen in his lifetime.

In "Marty Supreme," O'Leary plays the role of Milton Rockwell, a ruthless magnate. In 2025, O'Leary shared how he got the part, saying director Josh Safdie approached him, saying that he was looking for someone to play Milton Rockwell.

"He's the richest man in America in 1952, and we're looking for a real a--hole, you're it," Safdie told him. That statement brought back memories of the time when executive producer Mark Burnett was looking for someone to appear on "Shark Tank," and he was also approached for being an "a--hole."

"I'm starting to think this a--hole thing works for me," O'Leary joked. He didn't have experience acting, especially in a scripted movie, but he threw caution to the wind, saying, "I don't give a sh-t. I'm gonna do it."

Despite no acting lessons, O'Leary said that it was a bit "easy" to get into character, partly because of Timothee Chalamet's performance and Safdie's guidance. "I was never in a situation where I didn't feel totally in the moment. I was always right in it. I was not acting," he shared.

O'Leary's performance earned praise, and as for whether this means he will be acting more, he said he has already been sent two scripts, but admits "scheduling is a b-tch for this filmmaking stuff."

For now, O'Leary isn't ruling anything out, but a return to the screen will have to align with having a compelling script and free time from his demanding schedule.