Fast Money, Hard Lessons: NBA's Biggest Financial Falls

August 01, 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:

  • From Endorsements to Empty Accounts

  • From Ballin’ to Broke to Better

  • Burned Out After the Bulls

  • Living Fast, Spending Faster

💸Blew That Dough

Larry Johnson: From Grandmama to Gone Quiet

Larry Johnson, an up-and-coming NBA superstar in the 1990s, won an NCAA championship (1990), Naismith College Player of the Year (1991), and NBA Rookie of the Year (1991-92 season) all in the span of two seasons. He even made two All-Star appearances by the time he was 25. 

But after a third quality season with the Charlotte Hornets, he couldn’t take his strong play to the New York Knicks. Johnson went from superstar to role player almost overnight. He promptly left the league at age 32. How could a player’s career fall off a cliff like that? What happened? 

Johnson’s unraveling started with injuries. A herniated disk from a sprained back caused chronic pain and forced him to retire after the 2000-2001 season. His style of play was never the same after the initial injury in 1993.

However, things didn’t get any easier for Johnson after retiring. In the ensuing eight years, he fathered five children with four different women. This started a string of financial problems. Though he had $80 million in the bank when he left the league, he filed for bankruptcy in 2015. 

Even after selling his house to accommodate the expenses, Johnson was still strapped for cash. Between what he was shelling out in child support and his expenses, times got tough. One of the women still claims he has $30 million stashed in a private account and says she’s entitled to it, but it has never been found. 

Johnson eventually completed his college education, earning a Bachelor of Arts degree in social sciences from UNLV in 2007. He returned to the NBA in 2012 as a business operations specialist and player developer for the Knicks. His current salary is unknown, but he seems to be making a decent living as he tries to leave his ugly past behind. His life is a blueprint of what not to do if you’re a young athlete with a lot of money.

💰 Bounced Back

Antoine Walker: Fast Life, Hard Fall, Real Recovery 

Antoine Walker accomplished it all in the NBA. By the time he retired in 2008, he had a championship ring and $108 million to his name, marking the end of a fruitful 13-year career and the start of his post-basketball life. But that life came to an abrupt halt two years later. Walker filed for bankruptcy with $4.3 million in assets but $12.7 million in debt. 

How did this happen? Well, Walker was not used to having such cheddar in his pocket. He even admitted to this once. “I came into the league at 19 years old,” Walker told CNBC in a 2021 interview about his tremendous financial downfall. “I came from humble beginnings, so I was not used to having money at all.” 

The young kid in Walker saw those NBA earnings and tried to live the life of someone he wasn’t. He spent it all on lavish items like cars, clothes, and jewelry. His remaining funds were lost in real estate deals, which tanked in the 2009 market crash. 

It seemed Walker’s once-promising life, which had been built up by his even more promising NBA career, was gone. But the night is always darkest before the dawn. 

In 2012, Walker managed to bounce back and become debt-free. It required some sacrifices, like severely downsizing his lifestyle and even selling off his NBA championship ring for liquidation. 

Antoine immediately shifted into the role of an educator to help young future athletes avoid making the same mistakes he did. Walker later became an analyst for networks like FS1 and 120 Sports. He also started speaking at universities.

The most important lesson Walker learned from his curveball was not to look back with regret. “I may never make $108 million [again], but I can have a comfortable lifestyle,” he told CNBC in 2021. “That’s been my mindset as I got back on my feet.” 

Mission accomplished, Antoine.

💸 Moneyball Moments

Vin Baker earned over $100 million in his NBA career, but lost it all to bad investments and alcoholism. At one point, he was working at Starbucks, a job he embraced as part of rebuilding his life. Today, he’s an assistant coach with the Milwaukee Bucks and a vocal advocate for recovery.

💰Rings But No Bling

From Winning 2 Rings With Michael Jordan to Going Broke: The Jason Caffey Story

When you think of the greatest NBA teams of all time, the Michael Jordan-era Chicago Bulls have to be at or near the top of the list. The Bulls won six titles in eight years, a streak that very well may have been uninterrupted if Jordan hadn’t taken a career detour to play minor league baseball.

Any fan of 1990s basketball can name Scottie Pippen, Dennis Rodman, Horace Grant, and Toni Kukoc as integral parts of Jordan’s all-conquering Bulls. Many will also remember Luc Longley, B.J. Armstrong, Steve Kerr, and John Paxson. One player who seems to fall through the cracks, though, is Jason Caffey.

Caffey was the Bulls’ first-round pick in the 1995 draft. He won rings in his first two years in the league before being traded to Golden State in February of 1998. It was a puzzling move, given that Caffey sometimes started and was a quality role player. Even his former Bulls teammates didn’t understand it.

The silver lining for Caffey was that he was able to expand his game with the Warriors. He put up his two best scoring and rebounding seasons while in a Golden State uniform, and he also made good money with a seven-year, $35 million contract.

Caffey was eventually dealt to the Milwaukee Bucks in 2000, where he finished his career while going through some personal difficulties in 2003. The Bucks bought out the end of his deal, and that wrapped up his pro career.

Unfortunately, Caffey’s difficulties extended into retirement. He struggled to stay afloat because he was paying unfathomable amounts of child support for his 10 kids, whom he had with eight different women. Failure to keep up with those payments even landed him in jail for a time. He eventually filed for bankruptcy in 2007.

The story does have a happy ending, as Caffey was able to get his life back together. He briefly coached the Mobile Bay Hurricanes, an ABA expansion team, and co-authored Richard and the Boyz: The Puberty Experience, which aims to help adolescent boys navigate the wobbly waters of puberty. In the book, Caffey referenced his s**ual foibles in hopes of helping young men avoid the same mistakes he made.

In 2019, Caffey founded the Universal Youth Foundation, an Alabama-based non-profit that, among other initiatives, has organized numerous basketball camps and worked to improve relations between the community and the police. He also went back to school to finish his degree in physical education.

🏀 Life Saving Deal

How Reebok Brought Allen Iverson Back From Bankruptcy

The average NBA salary is just over $10 million, and that doesn’t even take into consideration the top talent, who earn significantly more. Although NBA contracts have ballooned in recent years, many past players raked in boatloads of dough, too.

One of the famed fortunate was Philadelphia 76ers star Allen Iverson. The 6-foot guard earned roughly $154 million in his 14-year career (1996-2010). That amount of money should have been enough for him to live a comfortable life and for many generations after him to thrive as well. Unfortunately, Iverson experienced a rude awakening following his retirement.

In a shocking turn of events, Iverson declared bankruptcy in 2012, brought about by irresponsible, extravagant spending. His splurges included luxury cars, late-night outings, and jewelry, according to Talksport.

All the work Iverson put forth during his career seemed to be for nothing. But even in his darkest moments, the fruits of his labor began to show. His unconventional decision to sign with Reebok over bigger-name competitors started to prove beneficial during this turbulent time.

Iverson has been a partner with Reebok since he entered the league in 1996. They took their partnership to new levels in 2001 with a contract requiring Reebok to issue AI an $800,000 payout per year for life. That income kept him afloat during his financial slide, but it wasn’t the biggest draw of the deal.

Once Iverson turns 55, which will be in 2030, he will gain access to a trust fund from Reebok. How much is the lump sum? $32 million. Iverson remained loyal to Reebok through the company’s highs and lows. In return, they have done the same for their marquee talent.

Now, Iverson has emerged as a key member of Reebok’s basketball department initiative. The president of their basketball division, Shaquille O’Neal, recruited him as his vice president in 2023. The income from that role is in addition to the money the 11-time All-Star is receiving from the company as part of his existing partnership with the brand.

At one point in time, Iverson may have seemingly lost it all. But Reebok had “The Answer” to solve AI’s financial problems.