Early Tiger Woods autographs pre-dating his monumental 1997 Masters victory are hard to come by in the hobby. Woods made his official PGA Tour debut as a 20-year-old at the Greater Milwaukee Open on August 29, 1996. He had already played in the Masters and The Open Championship as an amateur while competing for Stanford, but this was the first tournament as a pro where he could actually receive a paycheck. He shot under par both Thursday and Friday to sit in 8th place entering the weekend, but ended up finishing in 60th place. Seven months later, Tiger would begin his unprecedented run with 14 majors in 11 years, dominating the golf world unlike any player has before or since.

This generic white and black Nike hat is signed by Tiger on the front in lovely 9/10 black marker. The provenance is what makes this piece extra special as it came from a retired City of Milwaukee detective who directed the security for Tiger's first professional golf tournament. The included letter states that on the third day of the tournament, August 31, 1996, Woods signed this hat for him. One of the first items Tiger ever signed as a pro, if not the first. Also comes with LOAs from PSA/DNA (Mint 9 Auto.) and Beckett.