The younger brother to Jack by some 15 years, Terry had no two-sport choices to make in life as had Jack. Small, rugged, and fearless, he dreamed of the NHL from the get-go, though Jack's injuries also pointed to the ephemeral nature of a career in hockey.
Terry had been drafted 3rd overall by Chicago in 1966, though it was three years still before he ever played for the Hawks. He was with the Marlies for three years in the mid- to late 1960s and joined Father David Bauer's National Team for a season, in 1968-69, appearing for Canada at the 1969 World Championships. That fall, he made his NHL debut with Chicago, though he spent all but six games in the minors.
He was traded to Minnesota during 1970-71 but again played just eight games with the North Stars and the rest in the minors. Realizing his NHL dreams weren't likely to be fulfilled to any greater reward, Caffery signed with the WHA's New England Whalers that summer where he played most of the next five seasons.
However, Terry blew his knee out in a game near the end of the 1972-73 season and missed the entire year of 1973- 74 recovering. He played more or less regularly in the WHA, but his knee never fully recovered and he retired in 1976.