Sinclair was born in Lachine, Quebec. He was the youngest of Elizabeth and James Sinclair\'s four children and grew up in Montreal. Sinclair served with the Royal Canadian Air Force during the Second World War between 1943 and 1945. He then enrolled at McGill University where he earned a degree in commerce in 1949.\n', '

While attending McGill, Sinclair played collegiate hockey where he was a star right wing and centre over five seasons. He scored 53 goals in 52 games over that time and twice led the Redmen in scoring. In an February 25, 1949, game against the University of Montreal Carabins, Sinclair scored ten points (three goals, seven assists), tying a school record for points in one game that he continues to share. Serving as captain of the Redmen in 1948–49, he was named the most valuable player of the Senior Intercollegiate Hockey League after leading the circuit in scoring with 35 points in 12 games.\n', '

Sinclair joined the Sherbrooke Saints of the Quebec Senior Hockey League (QSHL) for the 1949–50 season. After scoring 46 points in 56 regular season games, he then led the QSHL in playoff scoring with 30 points in 22 post-season games. The Saints reached the Eastern Canada Final for the 1950 Allan Cup, but lost the series to Ontario champions Toronto Marlboros. The National Hockey League (NHL)\'s New York Rangers became interested in Sinclair as a result of his performance with Sherbrooke and signed him to a contract. Sinclair negotiated hard with New York general manager Frank Boucher and emerged with a two-year contract worth $25,000 in addition to a $10,000 signing bonus that made him the highest paid player on the Rangers.\n', '

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