Over the weekend, it came to light that attractive but mediocre tennis player Ashley Harkleroad had posed nude for a Playboy pictorial that will run in the August issue, prompting sports bloggers everywhere to scour Google Image Search for hints of what's to come.  Darren Rovell breaks down what it took for Harkleroad to end up in Playboy.

Playboy seems to signal the end of a marketing career for an athlete. It means you are accepting you won’t get blue chip endorsements so it’s time to cash in what you can get. That pretty much fits the mold for Harkleroad.

I remember watching Harkleroad’s U.S. Open debut in August 2001. Although she was playing on Court 11, she was the buzz of Flushing Meadows at the time. She was, after all, the next Anna Kournikova. And her outfit made me shy to even watch. I felt guilty. She was only 16…

But things didn’t pan out for Harkleroad. Her career high ranking–No. 39–was hit five years ago. Over the course of her career, she’s made less than $1 million playing tennis ($927,881). And she has managed to do one thing like Kournikova: she hasn’t won a WTA singles title.

Hmmm… there seems to be a bit of a "win or get naked" policy.  I like it.  But that would mean… wait a second.  Did Anna Kournikova not get a memo?