It almost feels wrong to ask the question, the way you’d never ask a parent which of their children is their favourite; even if you had an inkling of the answer.

But sometimes the question has to be asked.

In his 16-year CFL career, Ricky Ray won four Grey Cups. Two were in Edmonton and two were in Toronto. Which one meant the most to him? Can you choose a favourite?

“I mean, every one is a different story. Every one is a different team and a different place that you’re at individually in your career,” Ray said over the phone from his home in Redding, California. You could sense a but coming in his answer.

“But definitely I think 2017 will be one that I’m most grateful for. Just because of the point I was at in my career. I had a lot of injuries, had missed a lot of games. I didn’t even know if I was going to be playing in 2017 or where I was going to be playing if I got a chance to play, to be a starter. A lot of it was up in the air.”

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Ray’s favourite Grey Cup win, along with the Argos’ 2012 Grey Cup victory, will air Friday night on TSN1, as part of the network’s CFL Encore programming (starting at 7:30 ET). The night is themed Ricky Ray Night.

That 2017 Argos team was coming off of a five-win campaign that saw a new GM (Jim Popp) and head coach (Marc Trestman) arrive. The team had a massive roster overhaul and struggled through the first half of the season, losing five of six games at one point to fall to 4-7.

They got hot in September, though and found their run game with the emergence of James Wilder Jr. The Argos finished 9-9 and took first place in the East Division, squeaked past Saskatchewan in the East Final and then went to Ottawa and stunned Calgary in a wild game to take the 105th Grey Cup.

“Definitely one I’ll be really thankful for that I had the opportunity to taste that again, to feel that again before my time was up,” Ray said.

The pre-game blizzard that turned a perfectly clear TD Place field into near whiteout conditions at kickoff set the stage for a classic game. The heavily-favoured Stamps led 17-8 in the third quarter and took a 24-16 lead into the late stages of the fourth quarter and appeared to be in control when everything suddenly turned.

Calgary receiver Kamar Jorden was at Toronto’s eight-yard line when Jermaine Gabriel punched the ball loose. Cassius Vaughn snagged the ball and ran it back 109 yards for the touchdown. Ray found Declan Cross for the two-point convert to tie the game with 4:35 left. Lirim Hajrullahu sent a 32-yard field goal home to give the Argos a three-point lead with 53 seconds to go and Matt Black sealed the deal for Toronto when he intercepted Bo Levi Mitchell in the end zone with 20 seconds to play.

“That was just such a special year. That was probably the most fun I’ve had playing football,” Ray said.

“Just with how coach Trestman ran things, the atmosphere and the culture and how the whole year shook out. With his leadership and the kind of guys we had in the locker room, it just made it a really fun and exciting year.

“Everything played out the way he kind of led us to it. Looking back on a lot of things throughout the year, you’re just like, ‘Man, it played out just the way he’d planned for us.’ It made it made it a lot of fun to reflect on and a lot of fun to be a part of.”

When he looks at both Grey Cup-winning Argos teams he was a part of, Ray sees a similar path but two different kinds of teams. Ray’s trade to Toronto in Dec. 2011 hit him hard and it took that new group of players some time to gel. Like the 2017 squad, the 2012 team found its rhythm late in the season. There was a gratifying East semi win over Edmonton, then a narrow victory over Ray’s longtime rival in Montreal, Anthony Calvillo.

Toronto hosted the Grey Cup in 2012 — the 100th Grey Cup — and faced a Calgary team that wasn’t quite the powerhouse that it would become for the remainder of the decade.

“Going into the Grey Cup, I didn’t feel as much…like an underdog or anything,” Ray said.

“Going into that game I felt like we could beat them and we were a hot team and playing really well. We went out and got the lead and I think we played with the lead the whole game and really controlled the game from the get go.”

Nearing a full year of retirement, Ray hasn’t made any decisions yet about his future. He’s been rumoured to be a coach-in-waiting but he’s not sure if he wants to put the coaching lifestyle on his family at this point.

“This year I had some people call and ask me if I was interested going into this year and I still felt like I wanted some more time off,” he said.

“I know deep inside, I would love to be able to coach some day. Hopefully a year or two, maybe three I may get the want to get back into it and hopefully we’ll have an opportunity if that time does come.”

Even with the pandemic, Ray is enjoying the day-to-day of life. He’s spending time with his wife, Allyson and their daughters, Chloe and Olivia. He’s also taken up running. As in, serious distance running.

“I’ve done one ultra (marathon),” Ray said.

“I have some buddies that do trail running and there are a bunch of races all over that you can sign up for and I did one with them…a little over a year ago.

“I did my first race it was it was only 15 miles, 20 or 25 kilometers or something. I had a lot of fun doing it. I think it just gives me something to train for. I’ve been playing sports my whole life. I was always training for some kind of sport and this just gave gave me a way to get outside and stay in shape and train for something and be outside.

“I ended up doing two more trail races (last) year and a half-marathon. Then I did one ultra race, which was a 50-km last September, which was really hard. Trail running is a little different because you’re not necessarily running the whole time. There are times where you’re power hiking uphill because you got to go up in elevation, all that stuff.

“So you’re running and hiking and doing all of that. It was really tough. Obviously, it was the longest distance I’ve done but it was a lot of fun to finish it. It keeps me training towards something and gives me something to do.”