Winn was born in Los Angeles and attended San Ramon Valley High School. He attended college at Santa Clara University, and played baseball and basketball (where he played guard alongside former roommate and future NBA Most Valuable Player Steve Nash).\n', '

Winn was selected in the third round (65th overall) of the 1995 MLB amateur draft by the Florida Marlins. He was taken by the Tampa Bay Devil Rays in the 1997 MLB expansion draft.\n', '

Winn made his major league debut on May 11, 1998 as a pinch runner for the Tampa Bay Devil Rays. On October 3, 1999, he hit an inside-the-park grand slam against the New York Yankees. Winn represented Tampa Bay in the 2002 All-Star Game.\n', '

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