But he played it well. Described as "a good sized man, very fast on his skates, a dazzling stickhandler and a prolific scorer" in the book The Renfrew Millionaires, Whitcroft starred as an amateur in Peterborough. He later made name for himself professionally with Kenora, joining the Thistles just after their Stanley Cup victory, and Renfrew but especially out west in Edmonton.
Whitcroft may have found refuge in Edmonton following a nasty incident in Kenora. While playing for the Thistles he clubbed Montreal Wanderers star Moose Johnson from behind with his stick. It was suggested the Thistles were never quite the same after that, and Whitcroft headed west the next season.
Nonetheless Whitcroft remained amongst the very best in the west, and word of his dominance returned to the East soon enough.
In December 1909 Ambrose O'Brien, owner of the Renfrew Creamery Kings, was looking to build a super-team to win the Stanley Cup. Whitcroft was amongst his first targets, offering him $2,000 to return to the east. That was an exorbitant sum back then. Whitcroft jumped at it and played in only 5 games! Renfrew also had four other future Hockey Hall of Famers on the roster that year, but failed to win the Stanley Cup.
Whitcroft retired as a player soon after and returned to Edmonton to coach.