Big Checks, Bad Choices: NBA Stars Who Spent and Regretted

September 06, 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:

  • Pippen’s $4M Paperweight

  • Draymond Partied Too Hard

  • Haslem’s Guzzling Hummer

💸Jet Didn’t Fly

Scottie Pippen: The $4 Million Jet That Never Took Off

In 2002, Scottie Pippen made one of the most regrettable purchases of his post-Bulls career: a Gulfstream II jet. The price tag was reported to be about $4.3 million, but almost immediately after the deal closed, Pippen learned that the aircraft required nearly $1 million in engine repairs before it could be flown. What should have been a luxury quickly became a liability.

Pippen pursued legal action against the Chicago law firm Pedersen & Houpt, which had represented him in the purchase. Through his company, Air Pip, he alleged the attorneys failed to review the transaction and protect his financial interests properly. In June 2010, a Cook County jury agreed in part, awarding him $2 million in damages, though far less than the $8 million he had originally sought.

The case continued through appeals, and the judgment was ultimately reduced to about $790,000. Court records highlighted that the jet, already more than two decades old at the time of sale, had significant maintenance needs that were overlooked during the purchase process.

For Pippen, the outcome was frustrating. He had invested millions into an aircraft that never became operational and spent years in court, only to recover a fraction of his losses. The jet was never remembered for its intended use but instead became a case study in failed financial oversight.

Pippen’s ill-fated jet deal remains one of the most expensive cautionary tales among NBA stars. The lesson was clear: the price of luxury isn’t just the purchase, but the expertise required to make sure it’s worth the money.

💰 Partied too Hard

Draymond Green: A $21,000 Night Out Regret

NBA players are known to party hard, and the bills can pile up fast. Draymond Green learned that firsthand with one unforgettable night.

“I had a $21,000 night in the club,” Green admitted. Looking back, he said he could have had just as much fun spending $4,000.

Green, who once worked at car washes and diners in Saginaw, Michigan, to help his family, saw his three-year, $2.6 million rookie deal as life-changing. But he also recognized how easily money can slip away without discipline.

Now a four-time All-Star with over $200 million in career earnings, Green keeps his focus on saving and investing. “That’s $21,000 I can never get back,” he said. “People say: ‘That isn’t anything to you.’ $20,000 is still $20,000. I don’t care how much money you have, it’s still $20,000.”

Determined to become a billionaire before age 40, Green runs his decisions through one filter: does this help me reach that goal? His portfolio includes investments in Lobos 1707 Tequila, Blink Fitness, and Uninterrupted.

Green now encourages young athletes to ask questions, seek mentors, and learn financial literacy early to avoid costly mistakes. Reportedly worth $90 million as of 2025, he still has a way to go before billionaire status, but he’s confident: “I can reach it.”

The $21,000 party may have stung, but Green views it as a turning point. A reminder that even one bad night out can be a valuable lesson.

💸 Moneyball Moments

In 2001, Allen Iverson lost roughly $10 million in a single year, not on cars or jewelry, but on entourage expenses. His financial adviser estimated Iverson was paying for over 50 people’s travel, housing, and shopping bills. The costs spiraled so high that Reebok eventually structured his lifetime deal with a $32 million trust fund, locked until he turns 55.

💰Costly Wheels

Udonis Haslem: Yet Another Early 2000s Hummer Regret

When LeBron James gets a Hummer gifted to him with ‘under the table’ money as a high schooler, you know the craze revolving around that car is otherworldly. Udonis Haslem was yet another early 2000s kid who indulged in the same, but without the investigation.

Rookie contracts back in UD’s time paled in comparison to ones handed out in today’s league. Though even for 2003, signing a $986,977 deal was life-changing. This was Haslem’s contract that spanned from 2003-05.

Most would look at this sum and look to either invest it or spend it on assets that don’t depreciate the second they leave the lot. The latter didn’t really hit the Heat forward’s mind until he was given the power of hindsight two decades later.

“My first year was $400,000, and I spent half of that on that big dumba** H2 Hummer. The other half I spent gassing that big dumpster.” The H2 was never designed for fuel efficiency, much to Haslem’s chagrin. Its mileage is an atrocious 11-13 miles per gallon.

Calling it the “worst gas-guzzler” he’d ever seen in his life, he would go on to state it was the “dumbest idea” he ever had. Fair, considering that he earned less than $500,000 his rookie year, and about 80% went away with a Hummer.

Fortunately for Haslem, things only looked up from then on out. He wrapped up his career earning $71 million in total while securing himself a spot in the Heat organization, presumably for life.

Speaking on getting money at an early age, Udonis rejected the idea of NIL deals being good for teenage athletes. “Ain’t no way in hell we knew what to do with it (NIL money).”

Haslem pushes for more financial literacy to be bestowed upon the youth, especially when it comes to athletes earning millions of dollars before legally being able to drink.

So, while he does regret the H2 Hummer, it wasn’t all doom and gloom for him. And well, in all fairness, riding around in a Hummer in 2003 was the epitome of what was considered cool at the time. So perhaps UD has a couple of good memories he can look back to that came from the loss of $400k.