Kevin O’Leary, the Canadian investor and entrepreneur best known as “Mr. Wonderful” on ABC’s Emmy-winning Shark Tank, has recently revealed himself as one of three buyers behind the most expensive sports card sale: a one-of-one 2007-08 Upper Deck Exquisite Collection Dual Logoman card featuring NBA legends Michael Jordan and Kobe Bryant.

The ultra-rare card – which includes both players' autographs and logo patches cut from their game-worn jerseys – sold for US$12.9 million at Heritage Auctions on what would have been Kobe’s birthday, 23 August. Initially estimated at US$6 million, just above the previous record for a basketball card, the final price narrowly surpassed the US$12.6 million paid for a 1952 Topps Mickey Mantle #311 in August 2022.

O’Leary disclosed that he partnered with hobby veterans Matt “Shyne” Allen and Paul Warshaw to form a syndicate, allowing the trio to avoid a bidding war and secure the card together. In a televised interview this week, the 71-year-old said he doesn’t expect the card to return to the market in his lifetime. Instead, it will be part of an index he plans to grow with Allen and Warshaw. 

A Shark in the Card World

Known as “Mr. Wonderful” on Shark Tank, O’Leary has an estimated net worth of about US$400 million. He became a millionaire more than 25 years ago after selling his software company, SoftKey Products, to Mattel for US$4.2 billion in 1999. Today, he maintains investments in over 30 private companies and owns several businesses he founded, including O’Leary Fine Wines and O’Leary Ventures, his private venture capital firm.

In his Monday interview with CNBC, O’Leary said he joined the bidding group as “the analytical guy,” while Allen and Warshaw brought deep expertise in the sports card world.

“We stayed up until 3 in the morning on Saturday night... We got together on a Zoom call. My wife thinks I’m nuts. She just went to bed saying, ‘This is too crazy. You guys are all crazy.’ And I woke up the next day with her, and we owned the card.”

Inside the Winning Team

Allen – “the guy who did the research,” according to O’Leary – is widely recognized as one of the most prolific collectors in the hobby. On social media, he’s known as @Shyne150, and his display at Fanatics Fest 2024 featured a selection of cards valued at an estimated US$70 million.

“Normally, I would win a card like this at auction and keep it hidden until the new year at minimum,” Allen wrote in an Instagram post. “Yet this is an entirely different situation.”

Meanwhile, Miami-based entrepreneur Paul Warshaw, a well-known figure in the sports card world, is O’Leary’s business partner – and the one who first introduced him to the hobby.
 

From Skeptic to All In

When Warshaw brought him into the world of high-end sports cards three years ago, O’Leary – a seasoned investor – admitted he was initially skeptical.

“I said, ‘Why would anyone want to pay a million bucks for a piece of cardboard?’ He said, ‘You don’t get it.’ And I slowly kept looking at the numbers.”

Since then, he says he’s become “all in” – viewing high-end sports cards as a serious alternative asset class, on par with gold, Bitcoin, fine art, or luxury watches.

"I've kind of looked at the research back in contemporary art and modern art," O'Leary explained. "The majority of the capital gains accrue to the rarest Pollocks or Warhol pieces that are extraordinarily priced. You think, and then you wait a decade, look at them again, and see you get extraordinary capital gains. It's a very thin market, but as an alternative asset class, I'm all in."

“It’s no different than collectible watches, in some way,” he added. “It’s so rare that the prices continue to appreciate, and they seem to defy recessions.” 

He now aims to allocate around 5% of his investment portfolio to sports cards – the same weighting he gives to gold and crypto. “I can't believe how much interest there is in this thing called ‘the hobby’. Every father's son loved this trade."

The Card That Made History

The record-breaking card belongs to Upper Deck’s Exquisite Collection Dual Logoman Autographs series, produced between 2004 and 2009. Among the most coveted by modern basketball collectors, these are prized for combining game-worn NBA logo patches and autographs from two top-tier players.

This particular card is the only autographed Dual Logoman ever produced featuring both Jordan and Bryant. Jordan has eight cards in the series – four paired with LeBron James – while Bryant appears on eleven.

Notably, Jordan’s patch on the right is the gold variant used during the NBA’s 50th anniversary season in 1996-97, when he led the Bulls to the second championship of their second three-peat – making the card even more unique.

The Jordan/Kobe dual-signed Logoman is now the most expensive sports trading card ever sold at auction, surpassing both the US$12.6 million Mickey Mantle and the previous basketball card auction record: a Luka Dončić 2018 Panini National Treasures Logoman rookie card, which sold for US$3.12 million PWCC Marketplace in 2022 but had changed hands in a private sale a year earlier for US$4.6 million.

The all-time record for any known basketball card sale had been held by a one-of-one Stephen Curry 2009 Panini National Treasures Logoman autographed patch rookie card, which sold in a private transaction for US$5.9 million.

However, the Jordan/Kobe still falls short of the most expensive piece of sports memorabilia ever sold: Babe Ruth’s legendary 1932 “called shot” jersey, which fetched US$24.12 million at Heritage Auctions in 2023.