Toronto Arenas: 1918-19
The NHL started operations as a four-team league, and was one of a couple of leagues to challenge for the Stanley Cup. The number of teams in the league dropped to three almost immediately when the Montreal Wanderers’ arena burned down after just six games.
The three remaining teams in the NHL in 1918 were the Montreal Canadiens, Ottawa Senators (no relation), and the Toronto Arenas. Each team had just one jersey, so there were just three jerseys to pick which one is worst. This will be the last time you’ll see the Canadiens mentioned as contenders, as their design is gorgeous and timeless. Ottawa’s classic barber-pole design wasn’t pretty, but it was a steady look that worked while the team was winning.
The Arenas started NHL life with a plain blue sweater with a big T on the front. Yawn. By default, this was the worst jersey in the league. What did the team do to improve things the next season? Added stripes to the arms (good move), and the team name to the front. Why is that a problem? They kept the T there, so the front of the jersey actually spells “Aretnas, not Arenas. Yikes. The Arenas solved the problem by changing their name and colors to the St. Pats in 1919.