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

Canadian entrepreneur and TV personality Kevin O’Leary made headlines on the SAG Actor Awards, turning heads with an unexpected accessory. The daring selection served as a tribute to a late basketball legend, adding personal intending to his daring sense of favor.

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

Hanging on O’Leary’s neck was a Michael Jordan-Kobe Bryant basketball card fashioned right into a necklace. Furthermore, the cardboard was signed by the 2 basketball legends, increasing its value. In keeping with reports, the businessman said his accessory was value $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 cardboard was transformed right into a necklace. Per the caption, the necklace features a powerful 101 carats of diamonds and 10 carats of rubies set in white gold.

“The burden of this thing is over two kilos 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 an awesome investment. “I’m taking a look at this card at the identical way as for those who could have bought a Picasso in 1962,” adding that the cardboard has “done higher than crypto.”

Furthermore, the entrepreneur-turned-actor desired to honor the late Kobe Bryant. “I brought this back because I would like to bring Kobe back to LA on such a giant night in town,” adding that it is the first time he brought the basketball card out since his purchase.

The previous Los Angeles Lakers shooting guard passed away in a helicopter crash in January 2020. Amongst those that perished within 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 along with two other investors. Owning the cardboard was a dream come true for the businessman, who said that he had his eyes on the rare card for some years. It’s one other addition to his growing collection of basketball cards.

In an interview with CNBC, O’Leary compared the acquisition to his cryptocurrency and commodity investments, saying, “It may be an element of an index that I will proceed to grow together with my partners. We have a look at it no different than our bitcoin holdings, our ethereum holdings, our gold holdings.”

O’Leary said that purchases just like the basketball card proceed to understand, which is why it’s an excellent investment. As for whether the Upper Deck Exquisite Collection Dual Logoman card will return to the market, O’Leary said it won’t occur 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 in search of someone to play Milton Rockwell.

“He’s the richest man in America in 1952, and we’re in search of an actual a–hole, you are it,” Safdie told him. That statement brought back memories of the time when executive producer Mark Burnett was in search of someone to seem on “Shark Tank,” and he was also approached for being an “a–hole.”

“I’m beginning to think this a–hole thing works for me,” O’Leary joked. He did not have experience acting, especially in a scripted movie, but he threw caution to the wind, saying, “I do not 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 due to Timothee Chalamet’s performance and Safdie’s guidance. “I used to be never in a situation where I didn’t feel totally within the moment. I used to be all the time right in it. I used to be not acting,” he shared.

O’Leary’s performance earned praise, and as for whether this implies he can 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 is not ruling anything out, but a return to the screen may have to align with having a compelling script and free time from his demanding schedule.