Winter grew up in Hyde Park, NY and graduated from Franklin Delano Roosevelt High School in 1992, where he was a member of the varsity soccer and rowing teams. While in high school, he also represented the Hudson Valley in rowing in the Empire State Games. Upon graduation, he enrolled at Boston University where he was first introduced to rugby after failing to make the rowing team. At B.U., he was also a member of the Lambda Chi Alpha fraternity, but transferred to SUNY New Paltz after one year. There, he played rugby for the newly promoted Hawks in there first ever season in Division 1 in 1993 up until their playoff run in 1996. He then attended Northeastern University, playing rugby for the NU "Maddogs" throughout the remainder of his college career until his graduation in 1999. After college, Winter played briefly with Clontarf Rugby in Dublin, Ireland, making just a handful of appearances as a utility forward with their junior sides before the 2001 foot-and-mouth outbreak halted the majority of the 2001 rugby season. Following the lifting of the travel ban, Winter joined Bus Éireann RFC in the Leinster junior league for the remainder of their season.
Upon returning to the United States, Winter began his career with Mystic River in 2002, where he was a prop / utility forward. Secondary roles with the club included second row and the number 8 position. He played twelve years with the Mystics helping them to five Northeast Championships and five straight USA Rugby Division I Sweet 16 tournaments between 2008 and 2012, including three trips to the National Quarter-Finals. Due to injuries during the 2014–2015 season, Winter saw his playing time split between the Mystic's D1 side and the D2 Mystic Barbarians, suiting up for only two league matches that year.
International Rugby
Indonesia
Winter, whose father emigrated from Bandung, Indonesia, was named to the 42-man training squad for the Indonesian National Rugby Team after a trial session while in Bali in 2008. In 2009 he attended the national training camp held in Jakarta. He first wore the Indonesian jersey in June 2009 when he was selected to play for the Indonesian XV squad in the inaugural Minister's Cup, scoring a try and earning a position on the 28-man roster that would travel to Manila, the Philippines to compete in the HSBC Asian 5 Nations Tournament, part of the Rugby World Cup qualifier tournaments for countries in the Asian Rugby Football Union. On July 1, 2009, Winter made his international test match debut for Indonesia as the starting loose-head prop against Guam. Later that week, he would again start in the front row against Iran in the tournament consolation final, where the Rhinos would lose 48-13 and place 4th in the tournament.
Rugby League career
Boston Thirteens
In 2009, Winter signed with the Boston Thirteens in the American National Rugby League where he played prop, though he was forced to miss much of the second half of the season due to national team duties with Indonesia. Winter re-signed with Boston for the 2010 season, suiting up for all six matches at prop. He continued with the Boston Thirteens after the AMNRL/USARL split in 2011 as a utility forward. The following year, he was traded to Oneida FC, playing in just three matches before retiring from rugby league after the 2012 season.
Winter was named to the New England Immortals RLFC, a representative side consisting of the top players from the New England area. He made his rugby league rep side debut in July 2010 in an exhibition match against Canada at the 2010 AMNRL "War at the Shore" tournament.
