John Gregory, who led the Roughriders to their 2nd Gray Cup title as head coach, dies at 84

John Gregory, who led the Saskatchewan Roughriders to their second Gray Cup title in 1989, has died. He was 84 years old.

The cause of death was not immediately known. The Iowa Barnstormers, an Arena League team that Gregory also coaches, confirmed that Gregory passed away on Monday.

“We are deeply saddened to learn of the passing of legendary Iowa Barnstormers head coach John Gregory,” the team said. John was a big part of the Barnstormers organization and laid the foundations for Barnstormers football.

“Words cannot express how much he will be missed by the Barnstormers team, 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 as offensive line coach for the Winnipeg Blue Bombers in 1983. He was hired as Saskatchewan’s head coach in 1987.

After announcing an 11-7-0 record that earned Gregory the CFL’s Coach of the Year award in 1988, the Riders finished third in the Western Division 9-9 in 1989. However, Saskatchewan advanced to the Gray Cup game with sad playoff wins over Calgary and Edmonton.

Saskatchewan faced the Hamilton Tiger-Cats at the SkyDome and eventually prevailed 43-40 on Dave Ridgway’s 35-yard throw with three seconds left on rule time. This was the franchise’s second CFL title and the first since 1966.

For many, this match remains one of the most exciting games in Gray Cup history.

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

“On behalf of Rider Nation, the club offers its sincere condolences to the Gregory family, the players he has coached throughout his long and successful career, and all those lucky enough to know him.”

Glen Suitor, a former Riders defender and a member of the ’89 Gray Cup winning team, used social media to pay tribute to Gregory.

“An athlete never forgets the coach who believed in him and then supported them when their confidence was at an all-time low,” tweeted Suitor, a longtime football broadcaster at TSN and most recently entering the media wing of the Canadian Football Hall of Fame. One month in Regina. “RIP coach Gregory and thank you!”

Center John Gregory celebrates with Saskatchewan Roughriders coaches Ted Heath (left) and Ron Cherkus (right) after they beat the Edmonton Eskimos for the CFL Western Final in 1989. (CANADA PRESS)

The Riders fired Gregory early in the 1991 season and was replaced by the legendary Don Matthews. Gregory amassed a regular season record of 35-43-1 during his time at Regina.

He was hired by the Hamilton Tiger-Cats during the ’91 season and replaced 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, setting a record 24-40.

Also won a ring with Blue Bombers

With more than eight CFL seasons as head coach, Gregory had a regular season record of 61-82-1. He had a career playoff score of 5-4 with the Gray Cup title. He also won another ring while in Winnipeg.

“John Gregory was an 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) in Calgary, Toronto, and Edmonton. “He encouraged me to pursue my dream of a CFL career.

“An outstanding man, he will be missed by the many players he taught and inspired.”

Troy Westwood of Augustana University, who served as Winnipeg’s bookie and goalscorer for 18 seasons (1991-2007, 2009), said Gregory helped him on his way to football.

“Coach Gregory played an important role in getting my football scholarship,” he tweeted. “I have always been forever grateful to Coach Gregory.

A native of Webster City, Iowa, Gregory was an athlete in four sports in high school. He was an all state’s elite selection as a returning player as a senior back defender and won a scholarship from Northern Iowa University.

After his time in Canada, Gregory was named the Barnstormers’ first head coach in 1995. During his tenure at the club, Gregory later moved to St. He teamed up with quarterback Kurt Warner, who would previously lead the Louis Rams to the Super Bowl championship. Inducted into the Pro Football Hall of Fame.

“I’m so sorry to hear of John Gregory’s passing,” said John Hufnagel, president of the Stampeders. “He was a great football player and friend. I will always be grateful to him for giving me the opportunity to start my coaching career 25 years ago when I was head coach of the Saskatchewan Roughriders.

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

Arena Football League career

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

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 Honor (1996), and Webster City High School (1994).

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

Gregory also wrote a book called ‘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 that one lesson he took to coaching was writing commitment notes for himself. He first did this as a 1.70-foot-126-pound high school player.

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

“I went home crying all the way and sat on my bed and felt how stupid I was in my drawer and I looked at it every day.”

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

“When I first went to Canada, I wrote myself a note and pointed that out that I wanted to be a head coach and win the Gray Cup,” he said. “I didn’t tell anyone, but I promised myself.”

Gregory said it was his grandmother who taught him the importance of patience and determination. Every Sunday, Gregory and his family had dinner at his grandmother’s house where he played checkers with him.

“He beat me every time,” Gregory said. “I’d go crazy and knock over the board, I was a really bad sport.

“Once my aunt and uncle and mom and dad asked my grandma to let me win only once. But she said, ‘John will win when he deserves to win.’ Then I beat him, then I beat him again and again.

“There was a children’s checkers tournament in the city and I won it away and got a nice trophy, this is my first trophy. I won when I deserved to win and I always remember that.”

funeral services

Funerals will be held on January 31 in Gastonia, NC, according to Barnstormers. The club added that the Gregory family asked attendees to wear their favorite soccer jersey.

And instead of flowers, people are being asked to donate on Gregory’s behalf to or

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