Winter grew up in Hyde Park, New York and graduated from Franklin Delano Roosevelt High School in 1992, where he was a member of the varsity soccer and rowing teams.

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.

[6] Winter, whose father emigrated from Bandung, Indonesia, was named to the 42-man training squad for the Indonesian National Rugby Team (known as the Rhinos) after a trial session while in Bali in 2008.

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,[8] part of the Rugby World Cup qualifier tournaments for countries in the Asian Rugby Football Union.

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.