He began as a junior with first the Windsor Spitfires in 1951-52 followed by a move to the Barrie Flyers later that same season. A defenseman, Cherry played three seasons with Barrie, which concluded with a Memorial Cup championship in 1953.
Cherry turned professional with the AHL Hershey Bears in 1954, and following a full season with the Bears, made his one and only appearance in an NHL game with the Boston Bruins during the 1955 Stanley Cup playoffs.
The following two seasons were spent with the Bears before moving to the Springfield Indians, also of he AHL, where he clashed with cantankerous Indians owner and former legendary NHL defenseman Eddie Shore. Cherry would spend the next two and half seasons with the Indians before splitting the 1959-60 season with the Indians and the Trois-Rivieres Lions of the EPHL.
In 1960-61, he set a personal best of 39 points while skating for the Kitchner-Waterloo Beavers of the EPHL before moving on yet again, this time to the Sudbury Wolves in 1961-62 before finding himself back in Springfield for 11 games that same season.
A move west was in the cards for 1962-63, as Cherry joined the Spokane Comets of the Western Hockey League.
The 1963-64 season saw a move back east and a period of stability arrive when Cherry became a member of the Rochester Americans. Aside from 17 games with the Tulsa Oilers in 1965-66, he would spend the next six seasons with the Americans.
In addition to stability, success was also part of Cherry's time in Rochester, as they would win the Calder Cup during his second season with the Americans after they defeated his former club Hershey 4 games to 1.
Rochester went back-to-back when they defeated the Cleveland Barons 4-2 to claim the 1966 Calder Cup. Their streak of titles fell was stopped when they lost in the 1967 finals to the Pittsburgh Hornets but 1968 saw Cherry and the Americans take their third championship in four years when they defeated the Quebec Aces 4-2.
He would play one more season, splitting time between the Americans and the Vancouver Canucks of the WHL to close out his playing days - for now.
For the next two seasons Cherry worked as a car salesman, construction worker and painter before tiring of a non-hockey life and making a comeback as a player for the 1971-72 season with the Americans. Rochester was not playing well and Cherry wasn't getting much playing time as the parent club dictated the team to go with younger players. In an attempt to change the club's fortunes, Cherry was made the new head coach in the middle of the season.
He was an instant success as a head coach, winning Coach of the Year honors. The next year he also became the club's General Manager and followed that with another Coach of the Year award in 1974.
That success earned him a promotion to head coach of the Boston Bruins, a position he would hold for five seasons, guiding he Bruins to two Semifinals and two Stanley Cup Finals while earning the Jack Adams Award as Coach of the Year in 1976.
After being fired by the Bruins, Cherry landed a job as head coach of the Colorado Rockies, a tenure marked by several incidents which did not endear him to the club's management, including calling his own goaltender Hardy Âström "The Swedish Sieve"! His tenure in Colorado lasted but one season, bringing to an end his NHL coaching career.
Following the Rockies failure to qualify for the playoffs, Cherry was hired by the CBC as a studio analyst, starting him on the route to the career he is best known for today - along with his outlandish wardrobe!
Today's featured jersey is a 1967-68 Rochester Americans Don Cherry jersey. The Americans were founded back in 1956 and have six championships to date. Their shield logo is an icon of minor league hockey and remains in use today.
This classic minimalist style from Cherry's playing days features a lace-up collar, simple arm stripes and just enough stars to create a perfect balance with the crest and stripes.
Today's video segment is a departure from the usual, as we bring you "Keep Your Head Up Kid - The Don Cherry Story" in two parts of 90 minutes each. It's a fantastic look at Cherry's trials and tribulations during his minor league career on his way to becoming a head coach and media icon.
We've watched this film more than once and can't recommend it enough. There are some hilarious scenes in the movie and Jared Keeso as Cherry is just fantastic.