The sports card hobby has attracted its share of high-profile collectors in recent years, but few have a background in investing quite like Kevin O’Leary. Long before getting involved with cards, he was already collecting everything from watches to guitars, with a strong interest in alternative assets.
As his involvement in the hobby has grown, I recently had the opportunity to sit down with him and talk about his expanding role in the sports card world.
Where It All Began
When I asked him where his interest in sports cards began, he went back to when collector Shyne introduced him to the high-end card market while the two were attending a crypto conference in Dubai in August 2025. Shyne later invited him to join a group bidding on the one-of-one Michael Jordan and Kobe Bryant Dual Logoman, which ultimately sold for $12.9 million.
:// Generate —> #CardLadder#EyeCatchingSale
Eye-catching Sale: The 2007 Exquisite Collection Kobe Bryant / Michael Jordan #DL-KM Dual Logoman Autographs 1/1 PSA 6 sold for $12,932,000#TheHobby#SportsCardspic.twitter.com/6ym39y5STD
— Card Ladder (@CardLadder) August 24, 2025
“That was the beginning of my journey,” he said. From there, he had his team look back at the sports card market over the previous decade and came away comparing its potential to the art market in the 1950s. Looking to diversify into the space, he approached Shyne about building a collection of cards together, which they would call the “Wondershyne Index,” with Shyne helping choose the cards.
Secure Collectibles
That conversation led Shyne to tell him about Secure, the company he was building as a hobby, and ask if he wanted to become an investor. Kevin did, and his involvement in cards has only grown from there. “The thesis is, very simply, that this asset class is an alternative, no different than gold or crypto,” he explained. “This is the most fun I’ve ever had investing.”
That confidence in the asset class has left him open to putting even more money into the hobby. When I asked where sports cards rank within his overall portfolio, he said they make up around 2.5%, a number he would be willing to increase to 5% or potentially even higher. “From everybody I talk to, this isn’t going away,” he said, adding that he’s increasingly hearing from people in traditional equities asking him how they can get involved in the space.
We then discussed what people in the hobby can expect from Secure moving forward. Kevin said they’ve already assembled a full team and are exploring several areas of the hobby, mentioning plans around everything from vaulting to lending. At its core, though, he described Secure as a place to house their index. The plan is to raise additional capital and continue going into the market in search of more “piece-uniques,” with a focus on the best of the best and building a diversified collection.
Kevin also noted how he’d like to make that collection more accessible to the public, floating the idea of displaying the cards at museums on both the East and West coasts, potentially around Father’s Day.
Collector vs. Investor
That growing investment in cards has also made it harder for him to separate investor from collector. When I asked where he falls on that spectrum today, and whether there are cards he simply wouldn’t sell, he admitted he’s already having a hard time letting some of them go. “We get offers every day on different portions of the portfolio,” he said. “I can’t sell a piece-unique. I can’t sell the Ohtani. I’m never gonna get it back. You’re right, it’s a horrible virus.”
From there, I challenged him on one card I noticed in the index, a dual Logoman featuring LeBron James and Luka Doncic. Given his reputation on Shark Tank for structuring deals to limit his downside, I asked why he would be comfortable investing in a player like Doncic, who doesn’t carry the same established track record as names like LeBron James, Michael Jordan, Kobe Bryant or Stephen Curry.
Kevin acknowledged the risk and said he actually raised a similar concern with Shyne when he first saw the card. He pointed to Shohei Ohtani as another example of the uncertainty that can come with investing in an active player, whether through injury or something else. His view, though, is that the risk becomes easier to take as part of a larger index, as it’s only one piece of a much broader collection rather than an investment they’re relying on by itself. He also admitted to having a particular connection to Doncic after years of working alongside Mark Cuban on Shark Tank, who introduced him to Doncic and the Mavericks organization. We both acknowledged that maybe a bit of that inner collector in him is starting to come out after all.
Eyeing the Ultimate Grail
With that, I asked if there was any particular card he had his sights set on next, and one immediately came to mind. “Well, maybe I’m making news here, I don’t know, but there is a card; a very, very grail card, and we all know what it is. The 1952 Topps Mickey Mantle PSA 10,” he said. “If you’re a collector or investor, that’s the ultimate card.”
Today in 1997, Sports Cards Magazine & Price Guide bumped the 1952 Topps Mickey Mantle in a PSA 10 to $122,000.
29 years later, the card in a 10, is worth $50 million.
Pretty much beat out every stock over that time, minus Amazon (you’d have $252M) and Monster Beverage ($985M). pic.twitter.com/uX72EMHgvF
— Darren Rovell (@darrenrovell) September 22, 2026
With just three PSA 10 copies, he compared the prospect of owning one to buying the Mona Lisa, calling it “the most iconic card on earth” and something that would represent the pinnacle of the index. And when it comes to what he would be willing to pay, he suggested a card of that caliber almost transcends traditional pricing.
“I don’t know the price, but in some cases it doesn’t matter,” he said. “What’s it worth? Who knows. It ain’t gonna be cheap, I’ll tell you that.”
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Jason is an experienced basketball card collector with a focus on writing and educating others about the sports card industry. Find him on Instagram @jeancardz
