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I Played Tennis Against Drug Kingpin Freeway Rick Ross

Freeway Rick RossEXPAND
Freeway Rick Ross
Kristian C. Libman

Freeway Rick Ross was one of the most successful and famous drug dealers in American history. In the '80s he sold an estimated near-billion dollars of cocaine.

The South Central former kingpin inspired not one but two rappers to name themselves after him, Philadelphia heavyweight Freeway, and Miami hitmaker Rick Ross, who is literally a heavyweight, and whom the real Ross sued over his name. 

Things don't look good for that case, but after being released from prison in 2009 following 13 years inside, things are looking better for Ross himself. Having exited the drug game, he now does speaking gigs at fancy schools around the country, and though until he went to prison he was illiterate he recently self-published a memoir, Freeway Rick Ross: The Untold Autobiography, with Cathy Scott. It seems destined for Hollywood. Nick Cannon's apparently interested in optioning it.

The book is a good read, and taught me something new about the man: He was a high school tennis star. Hipped to the game by a generous local psychiatrist who bought him equipment named Doc — Ross won't divulge his real name — he eventually used his aunt's address to enroll at Dorsey High School, where he became one of the best singles players on a team stacked with talent. 

Recruited by Long Beach State, Ross's career was derailed when the coach found out he couldn't read. He eventually started selling drugs, buying wholesale from a Nicaraguan who funneled money to that country's rebel Contras. The CIA looked the other way, the Nicaraguan ratted on him (which is how Ross ended up behind bars), and a groundbreaking journalist killed himself. 

Boring! What I wanted to know, as a former high school regional champion myself, was: Could Ross still play tennis?

I Played Tennis Against Drug Kingpin Freeway Rick RossEXPAND
Kristian C. Libman

Yes, it turns out, he could. In fact, many of the federal prisons where he stayed had courts. Though he hadn't hit balls in a few years, he agreed to meet me at the Rancho Cienega courts, which is where the Dorsey team plays, and are right across from the mammoth Baldwin Village housing projects — formerly known as The Jungle. (You may remember them from Training Day.)

The courts themselves are bright blue, and the spot is now named for former champion Arthur Ashe, a UCLA alum who was known to play there. (He died from AIDS complications in 1993.) Long before the Williams sisters, Ashe was an inspiration to aspiring black tennis players, including Ross himself. "He was up on the pedestal for tennis," says Freeway. "At the time he was the best pro in the world." 

Upon our meeting, it's immediately clear that Ross is still in full (legal) hustler mode, wearing his "The Real Rick Ross Is Not a Rapper" t-shirt (which are for sale) and insisting his book will sell four million copies. Whatever he's doing, it's keeping him young. Dude looks amazing. Needless to say, he didn't smoke crack himself, and his face has no lines, though his beard has some grey. 

But whatever. I kicked his ass. We played one set, and I won 6-2. Take that, Freeway Rick Ross.

I probably should mention at this point that he's 54. Also, it was super hot and there is absolutely no shade on those courts. "Let's take a break," he said at one point. "My chest is burning."

Long!EXPAND
Long!
Kristian C. Libman

But what also may have led to his downfall was his absurd politeness. Like, we wouldn't call my balls out. Repeatedly, I'd hit serves that were long by six inches or more, and he played them. He also complained that he'd lost the timing in his backhand (it happens), and he, like I, was double-faulting like crazy.

But it was great talking to him. Much has been written about his drug-dealing exploits, but he seemed most interested in talking about his high school tennis glory days. It's crazy; he can remember the outcomes of specific matches, and can still name specific opponents, almost 40 years later. 

But whatever. Stop living in the past old man, I said as I spit on the court and stomped off.

Just kidding. What really happened was we shook hands and took a picture together.

I Played Tennis Against Drug Kingpin Freeway Rick RossEXPAND
Kristian C. Libman

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