After a successful career playing Junior B hockey in Toronto, Dryden was selected by the Boston Bruins in the 1964 amateur draft in the third round with the fourteenth pick. After the draft, Boston traded his rights to the Montreal Canadiens. Dryden had made it clear that he wanted to attend college, and while Montreal was willing to let him do that, they had their own plan for him. The team wanted him to play junior A in Peterborough and attend Trent University. Dryden, ever the individual, forged his own path.
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