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He made the big club during the [[1974–75 NHL season|1974–75 season]], and despite suffering injuries that restricted him to 47 games, scored 22 goals in that limited time. The following season was not as spectacular, as he scored 24 goals in 77 games while showing defensive deficiencies.
Middleton was traded to the Boston Bruins for [[Ken Hodge]] on May 26, 1976. Rangers head coach and general manager [[John Ferguson Sr.]] was confident that his team had enough young talent to justify making Middleton expendable. What the Bruins got was a player who was ten years younger and a swifter skater than Hodge.<ref>{{Cite news|url=https://www.nytimes.com/1976/05/27/archives/rangers-acquire-hodge-of-bruins-for-middleton-rangers-get-bruins.html|title=Rangers Acquire Hodge Of Bruins for Middleton|last=Eskenazi|first=Gerald|date=May 27, 1976|work=The New York Times|access-date=April 29, 2018}}</ref> The transaction became even more one-sided in favor of the Bruins when head coach [[Don Cherry]] developed Middleton's defensive skills to make him a solid two-way player.<ref>{{Cite news|url=https://www.nytimes.com/1983/01/15/sports/rick-middleton-s-new-priority.html|title=Rick Middleton's New Priority|last=Moran|first=Malcolm|date=January 15, 1983|work=The New York Times|access-date=April 19, 2018}}</ref> Hodge played only a single season more before his career ended, while Middleton became a great star in Boston, scoring a hat trick in his first game as a Bruin (October 7, 1976 versus Minnesota) and nearly nine hundred points in a Bruins uniform over the next twelve years. Generally paired with centre [[Barry Pederson]], Middleton had five straight seasons of at least forty goals and ninety points and led the Bruins to perennial glittering records. His leadership was apparent in being named [[captain (ice hockey)|co-captain]] (with [[Ray Bourque]]) to succeed [[Terry O'Reilly]] in 1985, a position he held until he retired, wearing the "C" during home games. Regarded as one of the best one
His best season was the [[1981–82 NHL season|1981–82 season]], during which Middleton scored a career high 51 goals, won the [[Lady Byng Trophy]] for excellence and sportsmanship, and was named to the NHL's Second All-Star Team. The following season he led the Bruins to the league's best regular season record, and set unbroken records that year for the most points scored in the playoffs by a player not advancing to the finals (33) and for a single playoff series (19, in the quarterfinals against Buffalo). His 105 points in the [[1983–84 NHL season|1983–84 season]] tied Ken Hodge's team record for most points scored in a season by a right winger, and remains unbroken.
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