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Former Toronto Argonauts’ general manager and coach Leo Cahill, left, poses with team president Ralph Sazio in 1985.John Felstead

In a previous life, Toronto Argonauts' former head coach Leo Cahill must have been a sideshow hawker, the guy who worked the circus crowd by telling it of the wondrous and uncommon attractions that waited for them inside the tent.

Consider who he had on his roster: the mustachioed defensive back who wrote poems and went by the nickname Tricky Dick; the long-haired tight end who owned a unisex clothing boutique and became an author and actor; the former University of Notre Dame quarterback who would go on to win a Super Bowl; and the Tampa, Fla., running back whose lasting images are of him scrambling to recover the football, and the championship, he has fumbled away.

Those players, characters all, were part of the 1971 Argonauts, a collection of free-thinking fun seekers that live in Canadian Football League infamy as the best team never to win a Grey Cup. And leading them was the calculating Mr. Cahill, who died on Feb. 15 at the age of 89.

As head coach, Mr. Cahill would talk up his players, extol their virtues then do anything to better their chances of winning. That was Mr. Cahill at his core: promoter, recruiter, the kind of coach who let his players revel in their individualism as long as they functioned as a unit on game day. He had a fondness, too, for making controversial remarks. He wasn't afraid to shake the tree and watch the nuts fall, even if they landed on him.

Take this classic tale from the 1969 East Division Final: Against the Ottawa Rough Riders, the Argos won the first encounter of the two-game, total-point series. Prior to the second game, Mr. Cahill joyously decreed, "It will take an act of God to beat us," which is exactly what happened. Ottawa crushed the Argos 32-3 after a storm front blew in and made for treacherous field conditions. It was a reminder of why the Argos' coach was known as Leo the Lip.

"I'm trying to think who you would relate him to in the modern era. I'm not sure there's anybody who is as flamboyant and outspoken as he was," said Peter Martin, who played for the Argos from 1965 to 1972 (mostly during Mr. Cahill's tenure as head coach). Mr. Martin joined Toronto's CFRB as a radio colour commentator during the Lip's second run as coach of the Argos (1977-78). Mr. Cahill went on to serve as the team's general manager.

"He was full of piss and vinegar," Mr. Martin added. "If there wasn't a story, he would create a story. The newspaper guys loved him. If it was a slow news day, [they'd] go talk to Leo and he'd come up with something."

Mr. Cahill was born in Utica, Ill., on July 30, 1928, to Catherine (née Coleman) and Dennis James Cahill. Football became his passion and he was good enough to earn a scholarship at the University of Illinois, where he was a member of the 1947 Rose Bowl team that beat UCLA by more than four touchdowns.

After a tour of duty in Korea with the U.S. Army, Mr. Cahill took to coaching at Illinois. He helped with the offensive line before moving to other opportunities. In 1960, he worked as an assistant with the Montreal Alouettes. Five years later, he became head coach of the Toronto Rifles of the semi-pro Continental Football League.

The Argos took note of the Rifles' success under Mr. Cahill and hired him in 1967. It was the start of a new era for pro football in Toronto, a time when the Argos flourished and their counterculture image made them loved by Torontonians and loathed by the rest of the country. On the roster: the Fu Manchu mustache-wearing Dick Thornton as Tricky Dick; the hippie pass catcher Mel Profit; Joe Theismann, the Notre Dame quarterback who would win a Super Bowl with the Washington Redskins; and super-slippery running back Leon McQuay, who was dubbed X-ray because X-rays are so fast you can't see them, he reasoned.

Those players, along with defensive back Tim Anderson and defensive linemen Jim Stillwagon (who also died this month) and Jim Corrigall, gave the Argos their swagger. Mr. Cahill gave them their cunning. Together, they made football matter in a city that would later turn its attention to baseball's Blue Jays and basketball's Raptors without ever losing its love for the NHL Maple Leafs.

"I appreciated the character Leo was because he coached a bunch of characters with character," said Mr. Theismann, who rattled off the names of his Toronto teammates who had played in the NFL or were collegiate all-Americans or serious students who studied serious subjects. "Mike Eben having a PhD in Germanic languages. Paul Desjardins having a PhD in biochemistry. Leo didn't have a whole bunch of normal people. I would call that [1971] group anything but normal."

Former Argos receiver Bobby Taylor acknowledged Mr. Cahill was "not my favourite coach by any stretch, but he put the Argos back on the map. We had 33,000 seats at [Exhibition Stadium] and we had 32,000 season-ticket holders. I figured we'd win some Grey Cups with him."

The Grey Cup they should have won was the 1971 rain-soaked showdown at Vancouver's Empire Stadium against the Calgary Stampeders. In that game, the Argos' offence failed to score a touchdown but was well positioned with the ball at the Calgary 11-yard line in the closing minutes of the fourth quarter. Mr. Theismann handed the ball to Mr. McQuay, who slipped on the turf and fumbled. Calgary's Reggie Holmes made the recovery in a 14-11 win.

Within a year, the Argos would go from a team of promise to one that lost 11 of 14 games and failed to make the playoffs. As the season wound down, Toronto fans began serenading Mr. Cahill with, "Goodbye Leo. We're glad to see you go." He co-authored a book with sportswriter Scott Young about his time and firing in Toronto, and titled it Goodbye Argos.

The players' biggest complaint about Mr. Cahill had to do with his coaching: He had to be involved in every aspect of the team, from running the offence to overseeing the defence to tinkering with the game plan right up until game day, sometimes rotating his quarterbacks (Mr. Theismann and Greg Barton) on every down.

"The thing with Leo that infuriated the players was he never seemed to be satisfied with a game plan," Mr. Martin said. "There would be times when we'd be in the dressing room ready to go out – referees would be yelling for us to go out for the national anthem – and he'd be making adjustments to the offence. We'd be lined up for the kickoff and he'd be, 'What if we do this?'"

Following Mr. Cahill's second stint coaching the team, the CBC hired him as a colour commentator for its CFL broadcasts, from 1981 to 1985. The team then hired him back to serve as general manager in the late 1980s.

Mr. Cahill underwent surgery a year ago for a bowel blockage, but his health continued to deteriorate so he moved to Atlanta to be with his family. His family and friends set up a GoFundMe account, requesting donations to cover his medical expenses. The final amount raised was US$34,450, with contributions coming from the Argos Alumni Association, the CFL Players' Association and from teammates and rivals alike. His family issued a statement soon after his death: "Even as his health began to fail, he was still razor sharp. Sarcastic and hilarious. In other words, still Leo."

Mr. Cahill was inducted into the Ontario Sports Hall of Fame in 2013. He married Shirley Smith and the couple had five children together before divorcing in 1977, after 22 years of marriage. Mr. Cahill leaves his children, Steve, Terry, Christy, Lisa and Bettye, along with seven grandchildren and three great-grandchildren.

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