Dryden was raised in Islington (then just outside Toronto) and Boston traded Dryden to the Montreal Canadiens, along with Alex Campbell, for Paul Reid and Guy Allen, whom the Bruins highly valued.
Dryden was raised in Islington (then just outside Toronto) and drafted fourteenth overall by the Boston Bruins in the 1964 NHL Amateur Draft. Later the same day, Boston traded Dryden to the Montreal Canadiens, along with Alex Campbell, for Paul Reid and Guy Allen, whom the Bruins highly valued.