Lyric discussion by jriemerm 

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

When I saw them in concert at First Avenue in Minneapolis, maybe around 1993, Gordon Downie introduced it saying "This is a song about wasted potential." The obvious meaning of that phrase is Bill Barilko's death. But I think there's another kind of wasted potential in the idea of a "fifty-mission cap", a veteran, probably in a crappy job, dreaming about his glory days in the war. Downie does a lot of that sort of thing, making great leaps from one story line to another, with a mysterious but undeniable continuity of theme between the two stories. This sort of thing happens in Pigeon Camera and Locked in The Trunk of a Car, too.

That's my take on it, anyway.