Milton was selected by the New York Yankees in the 1st round of the 1996 Major League Baseball Draft. He played one season in the Yankees minor league system and was then traded to the Minnesota Twins on February 6, 1998 in exchange for Chuck Knoblauch. He made his Major League debut on April 5, 1998 for the Twins against the Kansas City Royals, working six scoreless innings to pick up the victory. He was 8–14 in his debut season with a 5.64 ERA in 32 starts. On September 11, 1999, he struck out 13 batters in pitching a 7–0 no-hitter against the Anaheim Angels, the fifth no-hitter in Twins history. He finished the season with an ERA a full run lower than in his previous season, lowering it to 4.49 in 34 starts. He also completed 5 games with 2 shutouts. In 2000, Milton went 13-10 in 33 starts. He led the team in wins. In 2001, Milton enjoyed the best season of his career, going 15-7 with a career low 4.32 ERA and pitching in a career high 220 innings. In 2002, Milton made just 29 starts due to injury. He walked a career low 30 batters, he finished the season 13-9 with a 4.84 ERA in a career low 171 innings. He was limited to 3 starts in 2003 due to a knee injury. With Minnesota, Milton had a record of 57–51, with 715 strikeouts and a 4.76 ERA, and was selected to the 2001 AL All-Star team. He went 1–0 with a 1.65 ERA with the Twins in the 2002 and 2003 playoffs, and was traded to the Philadelphia Phillies for pitcher Carlos Silva and infielder Nick Punto following the 2003 season.
Philadelphia Phillies
Milton led the Phillies in wins, starts and strikeouts in 2004, going 14–6 with a 4.75 ERA and 171 strikeouts in 34 starts. He took a no-hitter into the 9th inning on July 25 against the Cubs but lost it before recording an out.
At the end of the 2004 season, he signed a three-year, $25 million contract as a free agent with Cincinnati. His record in 2005 with Cincinnati was 8–15 with a 6.47 ERA, one of the worst ERA's for a full-time starter in NL history. The following season, Milton lowered his ERA to 5.19 despite giving up 29 home runs in 26 starts. He finished 8-8 in just 26 starts after missing 3 weeks to repair a torn cartilage in his left knee. After lingering elbow problems in 2007, Milton underwent Tommy John surgery after just 4 starts, ending his season. Due to his poor performance and high contract, NPR of Minnesota called him a bust, ESPN named him to their all-overpaid team, and Sports Illustrated named him as the only pitcher on their all bust team, noting he gave up one home run per 11.9 batters.
New York Yankees
He left the Reds as a free agent after the 2007 season and went unsigned due to his injury history until signing a minor league deal with the New York Yankees on July 11, 2008. He never pitched for any of the Yankees minor league teams during 2008 however and was shortly released.
Milton signed a minor league contract with the Los Angeles Dodgers on February 10, 2009 with an invitation to spring training. He did not make the Major League team and was assigned to the AAA Albuquerque Isotopes to open the season. In 7 starts with the Isotopes, Milton was 3–2 with a 2.83 ERA. His contract was purchased by the Dodgers on May 14 and on May 16, Milton made his first appearance in the Major leagues since 2007 when he started for the Dodgers against the Florida Marlins. On May 26, Milton made his second start of the season for the Dodgers against the Colorado Rockies at Coors Field. He worked five innings in the Dodgers 7–1 victory, recording his first Major League win since September 12, 2006. He made a total of five starts for the Dodgers, with a 2–1 record and a 3.80 ERA. His season ended when he underwent surgery to remove a herniated disk on July 14.
Coaching
Milton joined the Maryland Terrapins baseball program in September 2011 as an assistant coach. On June 28, 2012, Milton was named the interim head coach of the Terrapins after head coach Erik Bakich left to take the head coaching position at the University of Michigan.
