"Since I didn't grow up in Chicago, I never gave it a thought," Alan Ruck, the actor who plays Cameron, tells MEL.
The Red Wings jersey was part of a convoluted backstory that was never revealed to viewers, he says.
"John [Hughes] had spent some of his boyhood in Detroit," Ruck continues. "[Hughes] had decided that Cameron had a horrible relationship with his father, but a great relationship with his grandfather, who lived in Detroit and would take Cameron to Red Wings games. That's all it was, and it was never explained in the movie."
The revelation provides further insight into Cameron's relationship with his father, whom he obviously despises. Assuming that Cameron's dad is a Blackhawks fan, Cameron's rooting for the Red Wings is an open act of rebellion against the old man.
It also rules out the theory that Cameron has recently moved to Chicago from Detroit and is just clinging to his sports roots.
"The psychology was that it was something that made Cameron feel good about himself, even though he was a Chicago kid," Ruck says.
The jersey is something of a security blanket for Cameron, then. This explains why Cameron chooses a Howe jersey, as opposed to that of some other Red Wings player. Howe was renowned for his toughness, playing in the NHL until he was a 52-year-old grandfather, and Cameron shields himself with that persona.
But the jersey is also a way for Cameron to assert his individuality, much like the winter cap Holden Caulfield wears in The Catcher in the Rye.
"If you look at the rest of what I wear [in the film], it's pretty straightforward — khaki pants and loafers. Nothing too crazy. [Cameron] was kind of a bottled-up kid, and his dad was authoritarian and had a lot of rules. The Red Wings jersey was his own little act of defiance—of saying, 'This is who I am.'"