Airballs Off the Court: NBA Stars Who Missed Billion-Dollar Plays

July 25, 2025

Welcome to Buckets and Riches — where NBA stars don’t just shoot threes, they stack Gs. From tunnel fits worth mortgages to endorsement empires and crypto hiccups, we break down how basketball’s elite earn it, flex it, and sometimes… brick it. 🏀💸

The latest edition of our newsletter covers:

  • Fortune Fumbled in Footwear

  • Billion-Dollar Brew Missed

  • No Crypto, No Fortune

💸Bag Fumbled

Magic Johnson: One Swoosh Away From a Fortune

Magic Johnson was the best at reading the basketball court and making the correct decision with the ball. He usually did it with his signature flair and smile, becoming one of the most endearing legends of the game.

Magic has made a lot of money on and off the court, too. His investments and endorsements range from big brands to the AIDS awareness cause, making him one of the most interesting cultural figures we’ve ever had.

Johnson has hosted his own talk show and has been featured in documentaries and TV shows. He’s been the president of basketball operations for his beloved Los Angeles Lakers. He’s a partial owner of the L.A. Dodgers, Washington Commanders, L.A. Sparks, Los Angeles Football Club, and the Washington Spirit. 

But when it comes to financial decisions, Johnson’s calls have not always been impeccable. One of his decisions was later proven to be a mistake that cost him billions. 

When Magic was first coming into the league, he had his choice of which shoe company to sign with. After all, he was the No. 1 pick in the draft, and he had just finished leading Michigan State to a national championship.

“Three companies came in: Converse, Adidas, and Nike. Nike was just a year or two old. And so, Converse offered me the most money. You know, when you grow up broke, you take the money,” Johnson told the All the Smoke podcast in 2022.

Nike wasn’t a big name at that point, so company co-founder Phil Knight couldn’t offer as much to Magic up front. He did offer stock, though, shares which would be worth over $5 billion today. Yes, billion with a ‘b’.

A few years later, Michael Jordan took Nike up on their offer, and the rest is history. Magic said he didn’t know anything about stocks at that point in his life. Even if he did, it would have been a risky bet to get into business with a company like Nike that didn’t have much of a track record at that time. 

Unlike today’s NBA players, pros back then couldn’t count on making life-changing money on the court. So, Magic can certainly be forgiven for taking the sure thing from Converse.

And Magic has no regrets either. “When you don’t know something, that’s OK. It’s when you know, and then you make mistakes. But I’m also a guy who never looks back. I live in the moment,” he said.

“I’m always moving forward,” Johnson continued. “If something happened to me that wasn’t good, I leave it in the past, and I keep moving forward. That’s who I am,” added Magic. 

It’s that kind of attitude that has allowed Magic to overcome everything in his life. From growing up poor to missing out on that Nike fortune to being diagnosed with AIDS, he’s kept moving forward. And he has been changing lives along the way, etching himself into the history books as a true living legend.

💰 Spilled The Beans

Shaquille O’Neal: “Black People Don’t Drink Coffee”

Shaquille O'Neal is a man who always knew how to get that bag. The Diesel has a net worth of roughly $500 million thanks to his lucrative NBA contracts when he was a player, his endless endorsements, his earnings as a TV personality on Inside the NBA, and his massive investment portfolio that includes Google, Papa John's, and more. 

However, Shaq did not always make the right investment play. He missed out on another cash-cow franchise, one that might have even catapulted him into billionaire status and probably would have required him to work a whole lot less. The Diesel, the General, whatever you want to call him, missed out on investing in Starbucks. 

Shaq once spoke about his big miss during an interview with Graham Gensinger. He mentioned how Howard Schultz approached him back in 1998 with the opportunity to establish over 100 Starbucks in Black neighborhoods. Shaq didn’t expect the idea to work. 

”Growing up in my household, I never saw a Black person drink coffee. So it was my thought process that Black people didn't drink coffee,” Shaq told Gensinger.

He later reiterated his ideology when it came to investments. “I'm always a guy that, if I don't believe in it, I can't do it. No amount of money can make me endorse something that I'm not 100% behind.” 

It was a decision that O’Neal would certainly regret, especially when he saw how successful Starbucks became. Magic Johnson took the deal, and the coffee chain took off like gangbusters. Years later, Magic sold his 50% stake in Starbucks and netted himself a sweet $70 million. 

While it’s not known whether Shaq’s deal would have been the same as his fellow Lakers legend, that’s still a whole lot of cheddar to be leaving on the table.

In 1998, Starbucks fluctuated between $4-$6 a share. Today, they are worth $95 per share. Say Shaq purchased one million shares for $5 apiece, that’s $5 million he would have thrown down. That $5 million is worth $95 million today. If O’Neal’s deal with Schultz had included a large number of assets like stock options, it would have dwarfed the $70 million Magic cashed in on. 

The Diesel does love having his name attached to greatness, in the business world, much like in basketball. But there is no No. 2 when it comes to the coffee world. Starbucks is on top, and Shaq was left in the dust. 

“Every time in every corner in every city in every country I see a Starbucks, and it stings,” O’Neal once told CNBC about not taking the deal. It’s okay, Shaq. You couldn’t have known.

💸 Moneyball Moments

At one point in the early 2000s, Allen Iverson turned down an equity deal with Reebok in favor of guaranteed money. He still secured a $32 million trust fund (available at age 55), but had he taken a slice of the brand’s future sales instead, he'd likely be worth significantly more today.

💰Crypto Failure

Tristan Thompson’s $32B Bitcoin Regret

The craze behind Bitcoin has its ebbs and flows, but it’s clear that there is more than just potential in this market. As of July 2025, the market cap for Bitcoin has reached a staggering $2.37 trillion. Hindsight is 20/20, and it’s easy to say everyone should’ve been on board. That logic Tristan Thompson is all too familiar with.

Thompson signed an $82 million contract in 2015 after quite a successful outing with LeBron James and the Cleveland Cavaliers. For 2015 standards, this was a solid deal for a player who wasn’t merely a plug-and-play starter, since the salary cap in 2015-16 was a modest $70 million.

Thompson, at the time, had the option to convert part of his salary into Bitcoin. In 2015, the price of BTC was around $270. He would have gotten the equivalent of $82 million. Fast-forward 10 years, and that same piece of the pie would be worth an otherworldly $31.75 billion.

The price of BTC today is around $119,000, a 440x increase from a decade prior. “It’d be so much, I’d be laughing and kicking, being like, ‘This is the best gamble in American sports history,’” said Tristan while reflecting on this missed opportunity.

“It was funny because, during that same time, a good friend of mine from Toronto, we had a basketball group chat, and he was like, ‘Guys, buy Bitcoin,’” Thompson recalled.

Of course, it isn’t all doom and gloom for the 2016 champ. He pointed out the volatility of the Bitcoin market and how the COVID-19 pandemic put the world’s economy in flux. 

“Would I have the education and knowledge to withstand that storm? Obviously, now the things I know and the knowledge and power that I’ve gained over the years, of course,” he said.

Regardless of Thompson’s past missed opportunities, he’s all in on cryptocurrency now. He’s even dabbling in Ethereum and recently posted a screenshot of ETH’s $385 billion market cap to social media, captioning it, “Ethereum up next?”

Many athletes have now jumped on the crypto bandwagon just like Tristan. Scottie Pippen’s social media accounts are littered with him promoting his cryptocurrency. Guys like Odell Beckham Jr. and Andre Iguodala have asked for their contracts to be fully or partially given in BTC.

A perfect encapsulation of Tristan’s feelings toward Crypto is what he said a while back: "It's not about buying Lambos. It's about buying freedom."