He was a big personality in a small league, too big, it sometimes felt, to be contained within its boundaries.

But somehow, a cozy, tradition-bound insiders club located in a country that tends to squirm around brash Americans, was a perfect fit for Don Matthews, a brilliant and cocky lone wolf who suffered from no lack of swagger.

He coached in the Canadian Football League’s largest city and its smallest, he thrived during the CFL’s short, doomed foray into the United States, he roared into town on his motorcycle, delivered Grey Cups with regularity, then hit the road en route to his next stop just in advance of – or just after – wearing out his welcome.

That long trek totalled 22 seasons as a head coach, 231 wins (only Wally Buono, Matthews polar-opposite in the personality department, has more), nine appearances in the Grey Cup game, five victories, and a place in the Canadian Football Hall of Fame. Aside from the two times when he was hired or fired mid-season, his teams never missed the playoffs.

His players loved him for his passion, his loyalty, and his willingness to go easy in practice – though he could be ruthless in making personnel decisions. Other coaches and general managers often feuded with him. Those who covered the CFL could in one minute be put off by his arrogance, and in the next see a different, softer side of the man, while all along being schooled in the nuances of the game.

Matthews was born in hard-scrabble circumstances in Massachusetts and died in Beaverton, Ore., following a five-year battle with cancer, but Canada was his professional home. He was a linebacker and a Marine who learned about the three-down version of the sport on Hugh Campbell’s staff in Edmonton, where the Eskimos won five championships in a row during Matthews’ five years on the job. After that, he struck out on his own as head coach of the B.C. Lions in 1983, taking over a franchise that participated in the Grey Cup game precisely twice since coming into the CFL in 1954, a near-statistical impossibility in a league that at the time had only nine teams.

His Lions made it to the Grey Cup in his first year as a CFL head coach, losing the championship game to the Toronto Argonauts. Two years later, the team featuring Roy Dewalt and Swervin’ Mervyn Fernandez defeated the Hamilton Tiger-Cats, winning Matthews’ first Cup as a head coach, and making football more popular in British Columbia than it had been since the heyday of Joe Kapp.

It wouldn’t be the last time Matthews would get credit for reviving a franchise in a league where fortunes tend to rise and fall dramatically.

By 1987, Matthews had exhausted any remaining goodwill in Vancouver and was fired. He resurfaced with the Argonauts in 1990, led the team to the playoffs, then during a tumultuous, uncertain period when the CFL’s very existence seemed to be in question, he took off for a job coaching the Orlando Thunder of the nascent (and doomed) United States Football League.

There was much speculation at the time that the next logical step for Matthews would be a job in the National Football League, and his name was associated with several coaching vacancies. But in a league that puts a high value on conformity, he never got the chance. Instead, he returned to Canada in 1991, taking over when John Gregory was fired by the Roughriders.

Matthews was unable to work his magic there, and left in a cloud of dust following the 1993 season, landing the next year in Baltimore as head coach of one of the CFL’s American expansion franchises, which would eventually be known as the Stallions. Unburdened by the rules that forced Canadian teams to employ a fixed quota of homegrown players, Matthews put together a powerhouse that lost to the Lions in the championship game in 1994 before crushing Doug Flutie and the Calgary Stampeders the following year, and taking Lord Grey’s mug south of the border for the first and only time in its long history.

The CFL’s American experiment ended there, and Matthews jumped to Toronto, where with Flutie at the helm his teams won consecutive Grey Cups, the coach’s second and third in a row.

In 1999 and 2000, Matthews returned for an unsuccessful stint with the Eskimos. It seemed for a moment as though his time had passed. And yet there would be a final renaissance, with the Montreal Alouettes team that had been built from the foundations of the club Matthews coached in Baltimore. In a four year stretch beginning in 2002, the Als appeared in three Grey Cup games, winning Matthews’ final championship in 2002.

Those last years, though successful on the field, also provided hints that Matthews might be physically, and emotionally, breaking down. (He would eventually acknowledge that he suffered from debilitating anxiety attacks.) In 2006, because of what were then undisclosed health issues, he stepped away as the coach of an Alouettes team that went on to play in the Grey Cup game.

His last season was a sad one, thrown to the wolves as the interim boss of a terrible Toronto team in 2008 that lost all of the eight games he coached to end the season.

After that, Matthews largely disappeared from the league in which he had been such a commanding presence, popping up for his Hall of Fame induction, and for a reunion of the 1985 Lions Grey Cup team, but otherwise living in Oregon, in the same town where long ago, before coming to Canada, he had coached the high school team.

The league has chugged along in his absence. Champions have been crowned, commissioners have come and gone, and the circle of those who experience The Don during his heyday has naturally diminished.

But as long as there’s someone left to say, “Hey do you remember the time…?”, his name will invariably come up.

That’s what happens when you’re a one off.