He led the team in scoring three more times and notched 20 or more goals in seven of his nine seasons with the club, recording a career-high 32 in 1958-59. The following season, McKenney posted a career-high 69 points and led the league with 49 assists, while also being named to the NHL's Third All-Star Team.
McKenney, known as a well-respected defensive forward, won the Lady Byng Trophy for Most Gentlemanly Player in 1959-60 and finished in the top four of the voting in six consecutive seasons from 1956-62.
In 1961, McKenney was named the club's 10th captain following the retirement of Fern Flaman. Overall, he played 592 games with Boston, collecting 195 goals (21st in Bruins history), 267 assists (23rd), and 462 points (22nd).
He was traded to the New York Rangers in 1962 and spent two seasons with the Blue Shirts, before finishing his career with stints in Toronto, Detroit, and St. Louis.
For his career, McKenney had 237 goals, 345 assists, and 582 points in 798 games across 13 NHL seasons.
Following his playing career, McKenney joined Flaman's staff as an assistant coach for the Northeastern University men's hockey team, a position he held for roughly two decades, before being elevated to head coach from 1989-91.
McKenney was inducted into the Northeastern Hall of Fame in 1999. He later went on to scout for the Colorado Avalanche.