A native of Toronto, Ontario, May was claimed 14th overall by the Buffalo Sabres at the 1990 NHL Entry Draft. A member of Canada’s 1991 Gold Medal World Junior Team, May showed plenty of spunk as a rookie with the Sabres in 1991-92 with eleven goals and 309 penalty minutes. In 1992-93, May’s defensive work improved and he scored the overtime winner in the first round playoff match up that eliminated the Boston Bruins.
After parts of seven seasons in Buffalo, May was traded to the Vancouver Canucks in February 1998 and was a steady hardnosed player for them over the next two and a half seasons. In June 2000, he was acquired by the Phoenix Coyotes to add grit to their fast skating team. May also played for the Colorado Avalanche before being dealt to the Anaheim Ducks, the trade proved to be a blessing in disguise as his physical presence led the Ducks to their first Stanley Cup championship in 2007.