After the Phoenix Coyotes were not able to come to terms with Wheeler, on July 1, 2008, Wheeler signed an entry-level contract with the Boston Bruins. The Coyotes received a compensatory second-round pick as a result of his signing elsewhere. On October 7, the Bruins made their final cuts for the 2008–09 season and Wheeler remained with the NHL club. Two days later, on October 9, Wheeler scored his first NHL goal, in his NHL debut, against goaltender Peter Budaj of the Colorado Avalanche. Wheeler then collected his first NHL hat trick the next month on November 6, against the Toronto Maple Leafs.