Former CFL head coach John Gregory dies at the age of 84

John Gregory, who guided the Saskatchewan Roughriders to their second Grey Cup title in 1989, has died. He was 84.

The cause of death wasn't immediately known. The Iowa Barnstormers, an Arena League team Gregory also coached, confirmed Gregory's passing Monday.

"We are deeply saddened to learn about the passing of legendary Iowa Barnstormers head coach John Gregory," the team said. "John was a huge part of the Barnstormers organization, laying the foundation for Barnstormers football.

"Words cannot express how much he will be missed by the Barnstormers staff, fans and community. Our deepest condolences to the Gregory family during this very difficult time. We love you, John."

Gregory began his CFL coaching career in 1983 as the Winnipeg Blue Bombers offensive line coach. He was hired as Saskatchewan's head coach in 1987.

After posting an 11-7-0 record in 1988 - which earned Gregory the CFL's coach of the year honour - the Riders finished third in the West Division in 1989 with a 9-9 mark. But Saskatchewan advanced to the Grey Cup game with upset playoff wins over Calgary and Edmonton.

Saskatchewan faced the Hamilton Tiger-Cats at the SkyDome, eventually prevailing 43-40 on Dave Ridgway's 35-yard field goal with three seconds remaining in regulation time. It was just the franchise's second CFL title and first since 1966.

For many, that game remains one of the most exciting in Grey Cup history.

"The Saskatchewan Roughriders are heartbroken to learn of the passing of our Grey Cup champion coach John Gregory," the Riders said in a statement. "He will be remembered as an incredible coach and an even better person.

"On behalf of Rider Nation, the club sends sincere condolences to the Gregory family, the players he coached over his long and successful career and all the people lucky enough to know him."

Glen Suitor, a former Riders defensive back and member of the '89 Grey Cup-winning team, took to social media to pay his respects to Gregory.

"An athlete never forgets that coach that believes in them, then backs them when their confidence is at an all time low," tweeted Suitor, a longtime football broadcaster with TSN who was inducted into the media wing of the Canadian Football Hall of Fame last month in Regina. "RIP coach Gregory and thank you!"

The Riders fired Gregory early in the 1991 season, replacing him with the legendary Don Matthews. Gregory compiled a 35-43-1 regular-season record during his time in Regina.

He was hired by the Hamilton Tiger-Cats during the '91 season, replacing David Beckman as head coach after the club's 0-8 start. Under Gregory, the Ticats reached the playoffs twice during his four years with the franchise, posting a 24-40 overall record.

Over eight CFL seasons as a head coach, Gregory had a 61-82-1 regular-season record. He had a 5-4 career playoff mark, with a Grey Cup title. He also earned another ring while with Winnipeg.

"John Gregory was the O-line coach in Winnipeg when I was at the University of Manitoba," said CFL commissioner Randy Ambrosie, who spent nine seasons in the CFL as an offensive lineman (1985-93) with Calgary, Toronto and Edmonton. "He encouraged me to pursue my dream of a CFL career.

"A remarkable man, he will be missed by the many players he taught and inspired."

Gregory, a native of Webster City, Iowa, was a four-sport athlete in high school. He was an elite all-state selection as a senior running back-linebacker-kick returner and earned a scholarship to the University of Northern Iowa.

Following his time in Canada, Gregory was named the first head coach of the Barnstormers in 1995. During his tenure with the club, Gregory teamed up with quarterback Kurt Warner, who’d later lead the St. Louis Rams to a Super Bowl title before being inducted into the Pro Football Hall of Fame.

"I'm very sad to learn of the passing of John Gregory," said Stampeders president John Hufnagel. "He was a great football man and friend I’ll always be grateful to him for giving me the opportunity to begin my coaching career 25 years ago when he was head coach of the Saskatchewan Roughriders.

"I learned a lot from John and I was very pleased in 2014 when he agreed to attend the Stampeders’ training camp as a guest coach. On behalf of the entire Stampeders organization, I offer my deepest condolences to John’s family and friends."

Gregory spent 16 seasons coaching in both the Arena Football League and afl2 from 1995 to 2011, compiling a 117-90 record.

He was named coach of the year in both the CFL and AFL and is a member of eight Halls of Fame, including the University of Northern Iowa (2003), Saskatchewan Roughriders Plaza of Honour (1996) and Webster City High School (1994).

Gregory served as the commissioner of the National Arena League before stepping down after the inaugural 2017 season.

Gregory also wrote a book, 'So You Want To Be a Football Coach,' which he penned with his wife, Carolyn.

In a 2019 interview with The Canadian Press, Gregory said one lesson he carried into coaching was writing commitment notes to himself. He first did that as a five-foot-six 126-pound high school player.

“I told my friends I was going to be a first-team all-state player as a senior and get a scholarship,” Gregory said at the time. “They all laughed at me and made fun of me like, ‘You’re not even going to have a chance.’

“I went home and cried all the way and sat down on my bed and felt what a fool I’d made of myself. But I wrote a note to myself that I was going to make all-state and get a scholarship. I put it in my drawer and looked at that every single day.”

Gregory also did that in 1983 when he joined the Blue Bombers.

“When I first went to Canada I wrote a note to myself that I wanted to be a head coach and win the Grey Cup and I pointed toward that,” he said. “I never told anyone, but I made a commitment to myself.”

Gregory said it was his grandmother who taught him the importance of patience and determination. Each Sunday, Gregory and his family had dinner at his grandmother’s residence, where he'd also play checkers with her.

“She beat me every time,” Gregory said. “I’d get mad and tip the board over, I was a really bad sport.

“One time, my aunt and uncle and mom and dad asked my grandmother to let me win just once. But she said, 'John will win when he deserves to win.' And then I beat her, then I beat her again and again.

“The city had a kids’ checkers tournament and I won it going away and got a nice trophy, my first trophy. I won when I deserved to win and I’ve always remembered that.”