After a spectacular career in junior with the Oshawa Generals, Middleton started his career in New York with the Rangers, who drafted 14th overall in 1973. He had great speed and puckhandling, but he was not well received in The Big Apple. He was often criticized for being lazy and weak defensively.
The Rangers grew impatient with him, and moved him to Boston. The Bruins offered the aging Ken Hodge to the Rangers, who jumped at the chance to reunite him with Phil Esposito. The two were great together early in the 1970s with the Bruins. The Rangers had hope to rekindle the magic in New York.
Ultimately, that never happened thanks mainly to father time. Middleton, meanwhile, exploded in Boston. He became an exciting fan favorite, even though he was not the typical Boston hockey hero. He was not rough and tumble, but rather a fancy pants with incredible stickhandling ability especially in traffic. Add to that his great skating which featured a couple different gears to change it up and he could deke defenders right on to the highlight reel.
Moreover, Middleton rounded out his game into a solid overall game. And he did it all very cleanly, only collecting 157 penalty minutes in over 1000 NHL games. In 1982 he won the Lady Byng Trophy in 1982.
Middleton, who teamed memorably with Barry Pederson, was Boston's top goal scorer from 1979 through 1984, scoring 38, 40, 44, 51, 49 and 47 goals in respective seasons. Only Mike Bossy, Wayne Gretzky and Marcel Dionne scored more goals in that time frame.
Despite that company, Middleton was never considered to be in that class. Perhaps he was nicely comparable to Lanny McDonald, who was right behind Middleton in goals in that time frame. Lanny was a more physical player, but Middleton, not McDonald was included on Team Canada 1981 and 1984 (playing with Wayne Gretzky). For whatever reason, McDonald (perhaps because he starred in Canada?) is in the Hockey Hall of Fame. Middleton is not.
Rick Middleton played in 1005 NHL games, scoring 448 goals, 540 goals and 998 points. He just missed the 500 goal and 1000 mark plateaus, which are generally considered as musts to be Hall of Fame material. His career was cut short by a nasty concussion. The helmetless Middleton took a puck to the temple in 1986, ending his season. He did return to play two more seasons, but he continued to suffer headaches that eventually ended his career.