Lyric discussion by edge24 

Cover art for Fifty-Mission Cap lyrics by Tragically Hip, The

Bill Barilko had gone on a fishing trip to James Bay, in a float plane with a friend from Timmins, Ontario (his hometown) a dentist named Henry Hudson (who was the pilot). Another Henry Hudson, the explorer (Hudson Bay is named after him) also died in James Bay. I just had this conversation about this song with writter Joseph Boyden who has taken Gord Downie fishing, up in James Bay, a few times.

There is an article on Barilko in the Beaver magazine August/Sept, 2001 issue.

Some of the lyrics are directly off a "PRO SET" hockey card.

The 50 mission cap is a separate thread woven into the Barilko story that I had assumed was a cap picked after so many tour dates...