In the 1940–41 season, he briefly played with the Toronto Marlboros, managed by Harold Ballard, whom Smythe had known since he was a young boy.
In March 1957, Smythe became chairman of a seven-person committee appointed by his father to run hockey operations for the Leafs.
Stafford accused Day of mismanaging younger players, especially those coming up from the Marlboros, and of sticking with an outdated defensive style of hockey.
Profitability was increased through expanded seating capacity at Maple Leaf Gardens and the sale of advertising to sponsors throughout the building.
Following an 8–7 vote of the board of directors on June 26, 1969; Smythe and Ballard were both fired, and Bassett was appointed president of the Gardens.
This proved to be a serious strategic blunder; Smythe was the largest single shareholder in Maple Leaf Gardens, and he and Ballard controlled almost half the company's stock between them.
Ballard would be convicted of tax evasion, but Smythe died of a bleeding ulcer at age 50 just before his trial was scheduled to begin.