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In the world of basketball, New York City is one of the sport’s meccas. From Madison Square Garden to Rucker Park, there’s no shortage of talent in the Big Apple; all-time greats like Kareem Abdul-Jabbar and more modern stars like Stephon Marbury cut their teeth on the city’s courts. Then there was Kenny Anderson.

While Anderson had plenty of talent and spent 14 seasons in the NBA, that didn’t make the guard invincible. After making $63 million playing basketball, Mr. Chibbs found himself bankrupt and coaching a high school in Florida.

Kenny Anderson’s impressive basketball career

Growing up in Queens, New York, Kenny Anderson’s talent was obvious from an early age. He cut his teeth in pick-up games and started attracting college recruiters in sixth grade; before long, he was starring for Archbishop Molloy High School and dominating the New York City basketball scene.

Anderson had his pick of college programs and headed to Georgia Tech. He spent two seasons with the Hornets averaging 23 points and seven assists per game; that was enough to make him the second-overall pick in the 1991 NBA draft.

The guard started out his professional career with the New Jersey Nets and, after a slow rookie season, developed into an All-Star. While he started bouncing between teams—Anderson spent time with the Nets, Hornets, Trail Blazers, Sonics, Celtics, Pacers, Hawks, and Clippers—he still made a solid living. During his 14 seasons in the NBA, the guard made approximately $63 million in salary. That reality, however, wouldn’t guarantee future success.

Declaring bankruptcy and coaching high school basketball

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As almost every sports fan can tell you, countless athletes fall into financial difficulties once their playing careers come to an end. Unfortunately, Kenny Anderson became one of those stars.

In 2005, shortly after he officially retired from the NBA, Anderson declared bankruptcy. “I thought [the money] would last and I didn’t know how to say no,” he told Forbes in 2015. “I had great attorneys that advised me well throughout my career, but I never listened.”

“I wasn’t a gambler or a drug addict,” he continued, “but I did foolish things.” Those things apparently included three separate marriages and having seven children with five different women.

Eventually, however, Anderson found his feet. The former guard earned a degree in organizational leadership and, in 2011, returned to basketball. He wasn’t joining an NBA organization or even a college program, though. Anderson became the head basketball coach at David Posnack Jewish Day School. Even that gig, however, wouldn’t end happily.

Where is Kenny Anderson today?

In 2013, Kenny Anderson was arrested and charged with driving under the influence. His contract with Posnack had expired at the end of the academic year; after his arrest, the school confirmed he wouldn’t be returning in September.

After that, Anderson bounced around for a bit. He headed to North Korea with Dennis Rodman; the former guard appeared on reality TV and starred in a documentary about his life. Then, in 2018, opportunity knocked once again.

Anderson returned to the bench, this time as the coach of Fisk University, a small HBCU in Nashville, Tennesse. While things still haven’t been a walk in the park—the school is far from an athletic powerhouse and Anderson suffered a stroke in February 2019—but the guard is still coaching the Bulldogs.

As Vince Lombardi told his Green Bay Packers, “It’s not whether you get knocked down, it’s whether you get up.” By that measure, Kenny Anderson is still an All-Star, even after retirement, bankruptcy, and everything else life threw at him.


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