Harold Darragh died on today’s date in 1993, a Wednesday. He was 90. Born in Ottawa in 1902, he was a younger brother to the early Ottawa Senators’ Hall-of-Famer Jack Darragh. Hal — they called him Hal — was a leftside winger who played nine seasons in the NHL, starting out with the Pittsburgh Pirates in 1925 and going on to skate for the Philadelphia Quakers and Boston Bruins before joining the Toronto Maple Leafs.

As a Pirate in 1928, Darragh won the Roosevelt Hotel Clean Play Trophy, one of the NHL’s short-lived New-York-hotel inspired trophies that pretended the Lady Byng didn’t exist. The Rangers’ Frank Boucher won the Byng that year, but Darragh was deemed saintlier when it came to the Roosevelt. He seems to have been the one-and-only recipient of the trophy.

Conn Smythe claimed Darragh for the Leafs when the Bruins waived him in 1931. He was the lightest of the 16 Leafs who convened at training camp for coach Art Duncan in St. Catharines, Ontario, that fall. Alex Levinsky weighed in at 212 pounds, while Darragh was a feathery 149. When the Leafs faltered in the season’s early going, Dick Irvin replaced Duncan behind the bench. Darragh seems to have played at least some of the season on a line with Bob Gracie (151 pounds) and Frank Finnigan (169 ½).

In April of 1932, the Leafs completed their revival by sweeping past the New York Rangers in three games to win the Stanley Cup. “Darragh is never spectacular,” Lou Marsh wrote in the Toronto Daily Star in the aftermath. “He is just quietly effective — a great man to have around when the other fellows threaten to break loose.”