Peter Mallouk leads bets with Mark Cuban as S&P 500 doubles stock picks

Creative Planning CEO Peter Mallouk is decisively ahead of Mark Cuban at the halfway point of their pair of 10-year stock market and cryptocurrency performance bets to benefit charity. 

The high-profile wager emerged from an April 2021 Twitter spat between the two billionaires that began with Mallouk criticizing Cuban’s vocal backing of the cryptocurrency Dogecoin. Their exchange eventually led to an agreed upon $1 million wager on their investment preferences—Mallouk siding with broad diversification versus stock-picking for Cuban. 

The $1 million bet was on the 10-year stock performance of Amazon and Netflix (Cuban) versus the S&P 500 index (Mallouk). Cuban’s concentrated choice—50% Netflix, 50% Amazon—has climbed about 39% since 2021—while Mallouk’s S&P 500 exposure has more than doubled that with around a 90% gain, as of an updated July 17 graphic from Creative Planning.  

“I think that the premise of going into the bets, which is that the S&P 500 is going to beat selecting a couple of stocks, your best picks — the S&P 500 is probably going to win that the majority of the time over a long period of time,” Mallouk said on his recent Signal or Noise? Podcast published by Creative Planning.  

Their other bet was on Cuban taking the 10-year performance of a 50-50 portfolio split of Bitcoin and Ethereum against Mallouk taking the S&P 500. As of Mallouk’s recent podcast episode recording earlier this month, Cuban’s crypto side was down seven percent over the past five years. 

“Crypto assets that don't produce earnings are likely to lag in assets that do produce some sort of earnings in the future, or have expected earnings probably over a long period of time,” said Mallouk, whose mega-RIA behemoth Creative Planning oversees over $700 billion in client assets. 

Mallouk says that community food network Harvesters and Pathway Financial Education are the two Kansas City-based charities that would benefit from his two active bets with Cuban totaling $2 million in anticipated donations. On his recent podcast with Creative Planning co-host Charlie Bilello, Mallouk said he was “closer to 70” percent confident in his chances at winning the two decade-long wagers. 

“When we made these bets, there was not total certainty. I consider them both in my favor, good bets, but not in the bag,” said Mallouk. “And even at the halfway part, I would say there's a long way to go, and anything can happen, and the odds are probably just a little bit better than they were five years ago.” 

Shared taste for sports ownership

While Cuban and Mallouk clashed on their stock market projections, the two have a shared interest in sports investing. The former Shark Tank star remains a minority owner in the Dallas Mavericks after he sold his majority stake in the NBA team in 2023, while Cuban is also part of Harbinger Sports Partners, a private equity group that just announced its minority stake in the Athletics ahead of the MLB team’s planned move to Las Vegas in 2028.

Mallouk has also been growing his sports portfolio, which originated with him investing in MLB's Kansas City Royals in 2019. More recently, he bought a majority stake in MLS club Sporting Kansas City in a deal that valued that franchise at $700 million, according to ESPN.