He became a reporter for Toronto's The Globe and Mail newspaper after graduating from university. After World War II, he was hired by the Toronto Telegram as advertising director.[2] His first experience in newspaper ownership was with the Sherbrooke Daily Record, which he bought from his father. In 1952, Bassett purchased part ownership of the Toronto Telegram. In 1960, he founded Telegram Corporation (later Baton Broadcasting) to run Toronto's first commercial television station, CFTO-TV. A few months later, he won the television rights to the Eastern Conference of the Canadian Football League. He needed a network in order to broadcast the games. The result was the Canadian Television Network, later to become CTV, with CFTO as the flagship station. Starting in the 1980s, Bassett began a drive to take over CTV by buying as many stations as possible. He succeeded in 1997, a year before his death.
In 1957, he was named to the "Silver Seven," a committee that oversaw hockey operations for the Toronto Maple Leafs. In 1961, longtime Maple Leafs owner Conn Smythe sold most of his shares in Maple Leaf Gardens Ltd. (which owned the Maple Leafs and Maple Leaf Gardens) to a partnership of his son Stafford, Toronto Marlboros president Harold Ballard and Bassett for $2.3 million. Smythe later claimed that he thought he was selling only to his son, but it is very unlikely that Stafford would have been able to raise the money on his own. Bassett became vice chairman of the Gardens' board of directors, ascending as chairman after Smythe resigned shortly after the Leaf’s won the Stanley Cup in 1962. Bassett's name appears on the Stanley Cup 4 times—in 1962, 1963, 1964, 1967.
In 1969, Ballard and Stafford Smythe were charged with tax evasion and accused of using Maple Leaf Gardens Ltd. to pay for their personal expenses. Bassett persuaded the board to fire Smythe as president and Ballard as executive vice president. The board elected Bassett as the new president.
However, Bassett did not force Smythe and Ballard to sell their shares, and they both remained on the board. This was a serious strategic blunder on Bassett's part; Smythe was still the largest shareholder, and he and Ballard controlled almost half the shares between them. A year later, Ballard and Smythe staged a proxy war to win back control. Faced with an untenable situation, Bassett resigned and sold his shares to Smythe and Ballard.
Bassett married fellow Bishop's University graduate Eleanor Moira Bradley of Sherbrooke on April 26, 1938, in the university's St. Mark's Chapel.[3] They had three children: John, Doug, and David. After their divorce, Bassett married Isabel Bassett on July 17, 1967.[4] They had three children (Avery, Sarah, and Matthew) and remained together until his death.