Jackson played 15 National Hockey League (NHL) seasons between 1929 and 1944 for the Toronto Maple Leafs, New York Americans, and Boston Bruins.

He was a member of the Maple Leafs' famed Kid Line with Joe Primeau and Charlie Conacher, one of the early NHL's dominant scoring trios.

Off the ice, Jackson was well-known for his high-spending lifestyle and drinking habit that prompted his trade from Toronto to New York in 1939.

Selke signed Jackson to a contract and assigned him to the Toronto Marlboros in the Ontario Hockey Association (OHA)'s junior league for the 1927–28 season.

[4] Jackson was a leading offensive player for Toronto in the 1929 Memorial Cup playdowns, scoring 15 goals and 25 points in 13 games.

[3] The Marlboros reached the final, defeating the Elmwood Millionaires in a best-of-three series to win the franchise's first Memorial Cup championship.

I told him I wasn't a stick boy, I was a hockey player, so he said I was nothing but a fresh busher [a term for someone who had just been called up from the minors] and the name stuck.

At 21 years, 3 months old, he became the youngest scoring champion in NHL history, a record he would hold until 1980–81, when it was broken by Wayne Gretzky.

While they remained consistent offensive performers, they lacked defensive ability and opposing teams began to find success playing their own top scoring lines against the trio.

[3] Following the season, the Maple Leafs traded him to the New York Americans, along with Jimmy Fowler, Murray Armstrong, Doc Romnes and Buzz Boll in exchange for Sweeney Schriner on May 18, 1939.

Though he played left wing throughout his career, the Bruins switched him part-time to defence when they lost players to injury or the Second world war.

[3] The Bruins reached the 1943 Stanley Cup Finals by defeating Montreal, but lost the series to the Detroit Red Wings in four straight games.

[24] Considered to have the looks of a movie star,[15] Jackson lived the lifestyle of a Hollywood actor during his playing career, spending money freely, driving fast cars, and attending posh parties.

[29] Though he was considered one of hockey's greatest left wingers[15] and was famed for his attacking style of play and backhand shot,[4] Jackson's personal problems led Hall chairman Conn Smythe to blacklist him from entry.

It would be another five years until the remainder of the selection committee finally overruled Smythe and posthumously inducted Jackson into the Hall of Fame in 1971.

[31] In 1975, Jackson was inducted into Canada's Sports Hall of Fame,[8] and The Hockey News ranked him 55th in its 1997 book, The Top 100 NHL players of All-Time.