Kevin O'Leary's Collectibles Bet Beat the S&P 500 - But There's a Catch

Popularly known as Mr. Wonderful, Kevin O'Leary has lived up to his nickname, taking a profit-driven and unsentimental approach to business and his investments. That's why some people might question one of his latest interests: collectibles. O'Leary has invested millions of dollars in watches and sports memorabilia. These investments might sound less like Wall Street choices and more like hobbies to people who don't understand his strategy. However, O'Leary believes that collectibles are profitable.

Should everyday investors looking to improve their financial fitness also take the leap and invest in the asset class? The answer might not be as simple as yes or no. This article walks you through O'Leary's investments and the factors to consider before buying collectibles.

Editor's note: This article is for informational purposes only and should not be considered investment advice.

O'Leary isn't just collecting items for sentimental reasons

Some people invest in collectibles for emotional and psychological reasons. For Kevin O'Leary, however, these assets are more than just dopamine and comfort providers; they're investments that could bring in considerable returns.

Mr. Wonderful has said on multiple occasions that he enjoys collecting high-value items. In an appearance on the YouTube channel Wrist Enthusiast, for example, he noted that he loves collecting watches. His collection includes many luxury pieces such as A. Lange & Söhne, Patek Philippe, Rolex Daytona, Audemars Piguet, and F.P. Journe.

O'Leary says he buys these brands not just because they align with his personal style but also because they appreciate. The legendary investor highlighted that he particularly loves the F.P. Journe collection because it has seen consistent value increases over the years.

Mr. Wonderful's biggest collectibles bet

O'Leary has been an avid collector for decades. However, nothing beats the Kobe Bryant and Michael Jordan sports card he bought at auction in 2025.

Kevin, along with two other investors, Matt Allen and Paul Warshaw, bought the card for nearly $13 million, breaking the record for the highest price paid at auction for a trading card. In an interview with CNBC, O'Leary said that he has no intention of selling the card. Instead, he plans to incorporate it into an index, stating that it's no different than his gold and crypto holdings.

In a separate interview with The Iced Coffee Podcast, Mr. Wonderful argued that the signed collectible is a unique piece, a feature that almost guarantees its appreciation. In fact, he noted that the card was already better than the S&P 500, having appreciated to an estimated $17.2 million by the time of the recording.

Is investing in collectibles a good idea?

For Kevin O'Leary? Yes. The Shark Tank investor already has a comprehensive investment portfolio, featuring everything from stocks and bonds to real estate. For him, collectibles such as the Kobe-Jordan sports card provide even more diversification. Their appeal particularly lies in the fact that they aren't tied to the traditional market. As such, they may provide O'Leary with a means to further spread his risk.

A collectibles investment strategy is also feasible for O'Leary because his vast net worth gives him the freedom to lock up significant sums of money in illiquid assets. What's more, he partners with other expert collectors rather than going at it alone.

What to consider before investing in collectibles

O'Leary's investment strategy works for him, but the situation is a little different for everyday investors. While you could invest in affordable collectibles worth a few thousand dollars, it's worth noting that they carry unusual risks, such as illiquidity and subjective valuation, as they could be difficult to sell quickly, and their worth might shift based on trends and perception. With that in mind, consider the following factors before you invest in the asset class.

Scarcity and demand

O'Leary has banked heavily on the scarcity of the signed Kobe-Jordan sports card. As a unique piece, the card's chances of increasing in value are quite high. What's more, there's a sense of exclusivity that comes with owning something that rare.

While scarcity might also be a valuable characteristic for everyday investors looking to get into collectibles, it shouldn't be the only one. A collectible's value lies not just in its rarity but also in its demand. So, look into each potential collectible's market. Otherwise, you might end up locking up money you'd use for other investments.

Condition

The value of collectibles also hinges on their condition. The better an item's state, the higher its likelihood of fetching good returns.

Carefully assess each potential collectible's condition before adding it to your portfolio. Look for signs of wear and tear such as discoloration and scratches, and identify any repairs that might affect its value.

Also, review items' grades and authenticity. For example, if you want to buy trading cards, request their PSA scale ratings, and invest in options with high scores.

Transaction costs

A collectible worth $5,000 might cost you more than that amount. Depending on your chosen asset and source, you may incur dealer markups, insurance premiums, authentication or grading fees, and storage costs. You might also have to pay auction or marketplace fees when you want to sell. These costs could take a significant chunk of your eventual profits.

To reduce your risk of making losses on collectibles, consider their all-in costs rather than just their buying price. Then, price the items accordingly when you decide to sell. For example, if you incur $1,000 in additional costs for your $5,000 asset, factor in the $1,000 when quoting the item.

Bottom line

Kevin O'Leary has increased his investment in collectibles. While it might be tempting to start investing in this asset class as well, be cautious, especially if you need or prefer liquid investments. The truth is, some collectibles require a lot of patience. You may need to wait for their demand to pick up, for authenticity verification, or for scarcity to grow.

If you want to diversify your portfolio and are comfortable with long-term investing, collectibles might be worth considering. However, if you're just getting started with building your portfolio, investments such as stocks and index funds may be a better fit.

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