 He was never selected in the NHL Entry Draft; he was signed as a free agent by the Washington Capitals on June 25, 1985.In his NHL career, he played for the Capitals, the Hartford Whalers, the Pittsburgh Penguins (with whom he won the Stanley Cup in 1991 and 1992), the Toronto Maple Leafs, and the Buffalo Sabres.Jennings appeared in 389 NHL games, scoring 14 goals and adding 43 assists.