Osborne attended Carson High School in Carson City, Nevada before he was drafted by the Montreal Expos in the 1987 Major League Baseball Draft. After declining to sign with the Expos, Osborne attended the University of Nevada, Las Vegas (University of Nevada, Las Vegas), where he played for the University of Nevada, Las Vegas Rebels baseball team
Out of University of Nevada, Las Vegas, Osborne was chosen by the Saint Louis Cardinals in the first round (13th overall) of the 1990 amateur draft. Osborne was the Cardinals" Opening Day starter in 1999, and he consistently produced season ERAs below four despite recurring battles with injury. He ranked among the National League top-10 in walks per nine innings, shutouts, European Research Area+, and strike-to-walk ratio.
At his peak, Osborne"s arsenal included a low 90"s fastball with late life, a plus changeup, and an average slider.
His control was regarded as excellent, and he was known to throw his fastball to all four quadrants of the strikezone. Ultimately, Osborne"s career was derailed by a series of severe shoulder injuries.
He was limited to 225 innings from 1997 to 2004, and he spent the entire 2003 season rehabbing his left shoulder. When Osborne started for the New York Yankees in 2004, he became the first Yankee pitcher since Babe Ruth to start for the team after not having started a game for over five years.
Osborne signed with the Long Island Ducks of the independent Atlantic League for the 2005 season, played for the Bridgeport Bluefish in 2006, and back with the Ducks in 2007 until his retirement on July 4, 2008.
