Kevin Glenn chooses Winnipeg over Saskatchewan as his favourite place to play in the CFL

Photo courtesy: Scott Grant /

Kevin Glenn made the most difficult decision of his CFL career in retirement: deciding between Regina and Winnipeg as the best place to play in Canada.

Glenn spent parts of six seasons in the Manitoba capital and five with Saskatchewan. He entered the league with the Riders while the Bombers provided the first chance for him to be a No. 1 QB in the three-down league.

“This is a tough one. I’m going to have to say Winnipeg. That’s where I got my first legitimate start being the starter on the team and it was my team,” Glenn said on The Rouge Report podcast.

“Listen, I’m going to have fans from Saskatchewan, family members out there, that are texting me right after they hear this. The first opportunity that you get that this is your team, it sits in your heart a little bit more.”

In Winnipeg, Glenn quickly developed into one of the best quarterbacks in the CFL. That was highlighted by his 2007 season when he threw for league-high 5,117 yards, 26 touchdowns versus 13 interceptions.

The Bombers were a Grey Cup favourite, however, Glenn suffered a broken arm in the East Final and Winnipeg lost to Saskatchewan in the CFL title game. If Glenn wasn’t injured many pundits believe the Bombers would have hoisted the Grey Cup.

Just a few years earlier, the Riders traded Glenn to Winnipeg without even knowing it. On May 19, 2004 the Argos acquired Glenn and turned around to deal him to the Bombers later in the same day. Toronto general manager Adam Rita delivered the news to Glenn.

“Winnipeg and Toronto knew that it was a backdoor deal, Saskatchewan and Kevin Glenn didn’t know,” Glenn said.

“I’m like, ‘Winnipeg?! What?!’ I was so distraught at the time. Divine intervention. It happened for a reason.”