I won two NBA titles with Michael Jordan but declared bankruptcy after losing $34m paying child support to eight different women

Michael Jordan’s Chicago Bulls dominated the NBA in the 1990s.

Scottie Pippen, Dennis Rodman, Toni Kukoc, Steve Kerr, John Paxson, and others helped His Airness on his way to basketball immortality.

Caffey won two championships with the BullsCredit: Getty
Jason Caffey was also part of the dynastic Bulls, winning two of the Bulls’ six NBA championships.

Caffey played college basketball at the University of Alabama for four years before he was drafted 20th overall by Chicago in 1995.

Caffey played the first three and a half seasons of his career with Chicago, winning the 199 and 1997 NBA titles.

He averaged 7.3 points per game during the Bulls’ second consecutive championship run in 199 –97 and started five playoff games, making him one of eleven Bulls players to start a playoff game amid their championship runs.

The ft 8in star was denied a third straight ring when he was traded halfway through the 1997-98 season to the Golden State Warriors.

He enjoyed the best statistical season of his career with the Dubs in 1999-2000, averaging a career-best 12 points and seven rebounds per game in 5 games started.

Caffey eventually joined the Milwaukee Bucks, where he would spend the final three years of his career before retiring in 2003.

The former forward earned an estimated $34,0 8,5 8 from his NBA contracts but quickly ran into financial difficulty amid an undiagnosed mental illness and bouts of depression and anxiety.

He struggled paying child support, having reportedly fathered ten children from eight different women.

Caffey reportedly owed more than $200,000 in child support and legal fees, and had debts of $1.9 million.

He starred alongside Michael Jordan, Scottie Pippen and Dennis RodmanCredit: Getty

He was traded to the Warriors halfway through the 1997-1998 seasonCredit: Getty

Caffey ended his career in MilwaukeeCredit: Getty
Upon retirement he was living in Mobile, Alabama, where he made a reported $11,500 a month from a string of day-care centers and a sports bar.

According to CNN, he spent time in jail for failure to pay child support and eventually filed for bankruptcy after racking up millions in debt.

In 2010, he was involved in an alleged domestic violence case as his life continued to spiral.

Thankfully, he has managed to turn his life around, using his experiences to help younger men speak about the perils of a frivolous sex life.

In 2019, he authored a book with Nadine Pierre-Louis geared for young men entitled: “Richard and The Boyz: The Puberty Experience,” designed to educate those at the most pivotal time of their sexual development.

“One thing about the NBA for me, battling mental illness, is it took me going to clinicals to find out what I was dealing with,” he told The Boston Globe in 2019.

“Being in the NBA was like being a rock star and then you’re playing with the best player in the world. It was tough for me, country boy, coming from Mobile. Definitely not used to that lifestyle, that kind of money. I always deal with women in abundance.

He went on: “Some of the things I did was very unethical. However, of those ten kids that I have, six of them are currently in college right now.

“My kids turned out real well. It’s because they had great mothers. I can’t say anything about them.”

He credits his former teammates for helping him get his life back on trackCredit: Getty

He has gone back to college and will graduate later this yearCredit: Getty

More recently, Caffey decided to return to college and finish a degree in Physical Education at the Alabama State University – the school he originally attended in the 1990s.

He was set to graduate in December 2024.

“I am proud to have chosen ASU as the school that I want to proudly one day soon say that I am one of its alumni,” Caffey said.

“I chose ASU also because it gives me that personal touch – a boutique experience – like a small elite academy, which will teach me and others world-class educational standards in a small class setting while preparing me for the future by reminding me of the toils of the past.”

After going through dark times, Caffey is on the right path and says he owes a lot to his former Bulls teammates.

“It’s no secret I went through a major downfall, some decisions I made in life after my basketball career,” Caffey said in 2020.

“But the teachings I learned from Michael Jordan, Scottie Pippen, Dennis Rodman – they’re the reason I’m still alive today and I’m still able to provide for myself.

“Had I not learned that ‘never say die’ mentality from those guys, there’s no telling where I might be.

“I thank the Lord for putting me in that position, with the best of the best.”

The Bulls of the 1990s are remembered for their six championships where their two three-peats were led by Jordan and Pippen and coached by Phil Jackson.

The 72 games won during the 1995/9 season was an NBA record that stood until the Golden State Warriors won 73 in the 2015/1 season. However, the Bulls have yet to regain their dominance since their last title in 1998.

The franchise, which has won six world championships, finished the 2024/2025 regular season with a 39–43 (.47 ) record.

They finished ninth in the Eastern Conference, gaining a berth into the Play-In Tournament.

However, the Bulls were eliminated from playoff contention for the third season in a row after losing in the first stage of the play-in tournament to the Miami Heat.