I earned two NBA championships alongside Michael Jordan and the Bulls but faced financial difficulties, including declaring bankruptcy, after spending $34 million on child support for eight women.

Caffey had a collegiate basketball career at the University of Alabama, spanning four years, before being selected as the 20th overall pick by the Chicago Bulls in 1995, where he joined the likes of MJ, Scottie Pippen, and Dennis Rodman.

During his time with the Bulls, Caffey secured two NBA championships, winning in 1996 and 1997. He contributed notably during the Bulls’ second consecutive championship run in 1996-97, averaging 7.3 points per game and starting in five playoff games, making him one of eleven Bulls players to start a playoff game during their championship runs.

Standing at 6 feet 8 inches tall, Caffey missed out on a third consecutive championship ring when he was traded midway through the 1997-98 season to the Golden State Warriors. However, he had a standout season with the Warriors in 1999-2000, recording career-high averages of 12 points and seven rebounds per game in 56 games started.

Following his stint with the Warriors, Caffey went on to join the Milwaukee Bucks for the final three years of his NBA career before retiring in 2003.

Despite earning an estimated $34,068,568 from his NBA contracts, Caffey faced financial challenges due to undiagnosed mental health issues, including depression and anxiety. He struggled with child support payments, reportedly fathering ten children from eight different women. His child support and legal fees accumulated to over $200,000, while he also had debts amounting to $1.9 million.

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