Jack Darragh was one of those old-time players who grew up, played and died in the same city - his home town of Ottawa, Ontario. He was a rarity in that he played right wing but was a left-hand shot. While not an unusual strategy today, in the early days of the century, playing on the "wrong wing" was pioneering. He was a superb skater, a very clever stickhandler and had a good backhand shot. As a result, Darragh was a prolific scorer. In 1919-20, he scored 22 goals in 23 games, and over his 13-year pro career he averaged better than a goal every two games. In an era of fierce and often violent hockey, Darragh also had a reputation for being a pacifist.
Darragh won four Stanley Cup championships, all with the Ottawa Senators. His first victory came in 1911 during two challenges. On March 13 the Sens defeated Galt, which had won the Ontario Professional Hockey League title. The 7-4 score was generous to Galt and Darragh was acknowledged to have been one of the best players on the ice. Three days later the Sens had to defend their championship against the Port Arthur Bearcats after the Bearcats had beaten Prince Albert to earn the right to challenge. This time the Senators swamped Port Arthur 14-4, with Marty Walsh scoring 10 goals and Darragh anchoring the defense once again.
Darragh's Senators made only one other foray for the Cup during the years of the NHA. In March 1915 the Senators and the Canadiens were tied for top spot in the league. The two teams played a two-game, total-goals series that Ottawa won 4-1. But in the best-of-five finals against the Pacific Coast champions, the Vancouver Millionaires, the Sens were no match and lost in three lopsided games.
While player movement in the early days of hockey was frequent - many players swapped teams between the NHA and PCHA - Darragh remained constant to Ottawa, a decision that reaped tremendous rewards once the NHA folded in 1917 and gave way to the NHL. In the spring of 1920, the Sens were champions of the new NHL and played the Seattle Metropolitans for the Stanley Cup. Although the best-of-five series was supposed to have been played entirely in Ottawa, mild weather forced the final two games to be shifted to the artificial ice of Toronto's Mutual Street Arena. In game one of the series, Darragh scored the game-winning goal in a 3-2 win, and in the fifth and deciding game for the Cup, he scored a hat-trick in a 6-1 clobbering of the Mets.
The next season the Sens again won the Cup, and again Darragh was the hero. The best-of-five series was played in Vancouver that year and once more the Cup was decided in the fifth game. Darragh scored both Ottawa goals in a 2-1 win and the Senators became the first NHL team to win consecutive Cups. In all, Darragh had seven goals in seven playoff games in 1921.
Darragh took the entire 1921-22 season off, but when he returned to the Senators the next year, it was as though nothing had changed. The Sens beat first the Millionaires and then the Edmonton Eskimos to win their third Stanley Cup in four years. Darragh played one more full season in the NHL, but in the summer of 1924 he succumbed to peritonitis.