Winchester spent two seasons with the U.S. National Team Development Program, then moved to his hometown
University of Wisconsin–Madison, where he played for four seasons. At six feet, five inches tall and 228 pounds, was the largest player the Oilers had drafted since the
1995 NHL entry draft. In December 2000, Winchester participated in the
World Junior Hockey Championship with the United States, finishing in fourth position. Winchester made his professional debut in the
2003–04 American Hockey League season, playing for Edmonton's farm affiliate, the
Toronto Roadrunners. He moved with the team to Edmonton during the
2004–05 NHL lockout, where he tied for the team lead in goals and was six points behind
Tony Salmelainen and
Raffi Torres for the team scoring lead. Winchester split
2005–06 between the Oilers and the
Hamilton Bulldogs, going scoreless during the NHL regular season but scoring the game-winning goal in his playoff debut, the second game of a series with the number one seeded
Detroit Red Wings. His goal gave the eighth seeded Oilers their first win in the series on the road. The Oilers went on to lose to the
Carolina Hurricanes in seven games of the Stanley Cup Finals, with Winchester spending most of the latter games as a healthy scratch. On June 26, 2007, the Oilers declined to make Winchester a qualifying offer, which allowed him to become an unrestricted free agent as of July 1, and on the 6th, he signed with the
Dallas Stars. After playing in 41 games for Dallas in 2007–08, Winchester signed with the
St. Louis Blues on July 10, 2008. He was recalled from the Blues'
Peoria Rivermen (
AHL) affiliate on November 20, 2008. On February 28, 2011, Winchester was traded from the Blues to the
Anaheim Ducks for a 3rd round draft pick in
2012. On October 3, 2011, Winchester signed a one-year, $725,000 deal with the
San Jose Sharks. A free agent through the duration of the
2012–13 NHL lockout, Winchester accepted a try-out to the
Calgary Flames training camp once the dispute was resolved on January 12, 2013. At the conclusion of camp, Winchester was unsuccessful and released by the Flames. On January 22, midway through the
2012–13 AHL season, Winchester signed a professional try-out with the
Milwaukee Admirals. On July 24, 2013, Winchester agreed to a one-year contract as a free agent with the
Chicago Blackhawks. He was assigned to AHL affiliate, the
Rockford IceHogs, to start the
2013–14 season. On February 26, 2014, Winchester was traded by the Blackhawks to the
Minnesota Wild in exchange for
Brian Connelly. Winchester was not re-signed by the Wild after the conclusion of the season and on September 11, 2014, the Norfolk Admirals announced they had signed him. Winchester recorded 9 points in 15 games before suffering a shoulder injury with the Admirals on January 15, 2015. Winchester was traded by Norfolk to the
Oklahoma City Barons for future considerations on March 6, 2015. On September 17, 2015, Winchester announced he was retiring from professional hockey. ==Personal==