The 12-year veteran will play for his fifth ring when the Stampeders face the Toronto Argonauts on Sunday at Rogers Centre in the iconic game's 100th anniversary.
A heady accomplishment, considering Stewart was forced to spend eight months wondering if he'd even play this season. He was released in February by Montreal following 10 seasons there and wasn't signed by Calgary until Oct. 12.
Despite his many trips to the Grey Cup, the 36-year-old Stewart says it never gets old.
"Yeah, yeah you get that feeling, it's in the stomach, the butterflies," Stewart said Saturday following Calgary's walkthrough at Rogers Centre. "The thing about me is I might be a crybaby but I get really emotional.
"When I think about the game, where I've come from, how far God has blessed me, it's a real honour to be here. (Calgary quarterback) Glenn was talking to us earlier today and this is his 12th year and he's never been to a Grey Cup. In 2007 he broke his arm so he wasn't able to play and I look at it and this is my ninth Grey Cup. You never stop getting that feeling.''
The six-foot-four, 255-pound Stewart made seven Grey Cup appearances with Montreal from 2002 to 2011, winning three times. He earned his first Grey Cup ring in 2001 with Calgary, but doesn't get credit for playing in the Stampeders' 27-19 upset win over Winnipeg because he wasn't on the roster. As a result, when he steps on the field on Sunday, Stewart will be making his eighth official Grey Cup appearance, one shy of the league record.
Stewart got credit for his first Grey Cup contest in 2002, when Montreal's 25-16 win over Edmonton thwarted the Eskimos' bid to capture the CFL title game on home soil. Ironically, its the same challenge Stewart and the Stampeders will face Sunday at Rogers Centre.
"It was crazy, it was cold," Stewart said of the '02 Grey Cup game. "I kind of knew what to expect but I really didn't.
"Now, I'm the older guy so I understand the emotions, why guys are crying. Why guys are by themselves and why they're isolated because you need to have that type of preparation. You've got to dream these things, you've got to visualize these things and I think when you do those type of things there's a connection.''
Experience has also taught Stewart that the Grey Cup is anything but just another football game.
"I told the guys that when they come here tomorrow the lights are going to be five times brighter, there's going to be so much stuff going on and sometimes you're not going to be able to breathe," Stewart said. "I told them they're just going to have to relax, take it all in and at the end of the day just try to take it as a normal game.''
That's easier said than done for Toronto safety Jordan Younger, who will make his second Grey Cup appearance Sunday but first since winning with the Argos in '04 as a rookie.
"When I talk to the guys I try to make them aware just how special the moment is, how influential the moment is," said the 34-year-old Younger. "This is the 100th Grey Cup, this moment is going to be recorded and remembered for a long long long time and a lot of people are going to care about this moment for a long time.
"The ring is a bonus, you love having the ring. But it's about having the experience and being able to say you were the best.''
The Stampeders head into Sunday's showdown as slight two-point favourites despite Toronto sweeping the season series against Calgary 2-0 this season. In fact, the Argos have won their last five straight contests against the West Division champions.
And Toronto will certainly have home-field advantage, becoming the second straight CFL team to reach the Grey Cup in its home city. The Argos will look to follow in the footsteps of the B.C. Lions, who won last year's championship contest at B.C. Place against Winnipeg.
The atmosphere will be electric, with more than 52,000 spectators crammed into Rogers Centre — which usually has a seating capacity of about 46,000 for football. It will mark the second time since '07 the facility will play host to the CFL title game.
Earlier this week, the Queen extended her best wishes to Canadians leading up to the historic football game, saying the 100th Grey Cup coincides with her Diamond Jubilee as Queen of Canada.
Toronto will be making a third Grey Cup appearance at home in 60 years, winning 21-11 in '52 against Edmonton at Varsity stadium before dropping the '82 finale 32-16 to the Eskimos at Exhibition Stadium.
Toronto and Calgary are meeting in the Grey Cup for the third time. The Stampeders earned a controversial 14-11 victory in '71 on Leon McQuay's late fumble before Raghib (Rocket) Ismail's 87-yard kickoff return TD guided the Argos to a 36-21 victory in the '92 championship contest.
But Stewart and Younger and their teammates won't be the biggest stars on the field Sunday.
Teen heart-throb Justin Bieber and pop star Carly Rae Jepsen headline the Grey Cup halftime show that will also feature singer-songwriter Gordon Lightfoot and pop-rock group Marianas Trench. Country star Johnny Reid and veteran rocker Burton Cummings will perform in a special pre-game show.
When the focus returns to football, Stewart said Calgary's gameplan will be simple: Get to Toronto quarterback Ricky Ray, who has thrown 11 TDs against one interception in his last four starts since returning from a knee injury.
"The one thing you have to do in a game like this is start fast and stay focused,'' Stewart said. "When you can do that and you can jump on somebody early, especially in a game like this being in this stadium it will take the crowd out of the game.
"At the end of the day defensively we have to get after Ricky Ray, we have to apply the pressure early and see what happens.''
Grey Cup week consists of parties, social events, news conferences and endless distractions and demands on the players' and coaches time. Younger, for one, is ready to just play football.
"I've been dreaming about this since we found out we were getting the 100th Grey Cup," Younger said. "Don't get me wrong, I wouldn't trade it for the world but (Grey Cup week) is draining because there are so many different requirements, extra requirements that don't happen during the course of the regular season or even the regular playoff games.
"Our guys have handled it well, very maturely and professionally but we're itching, we're ready to play now."
One of the perks for members of the winning team is being able to have the Grey Cup in their possession for a day, and if the Stampeders are victorious Stewart has definite plans for the trophy.
"What I'd like to do is get the Grey Cup and bring it to Montreal for a couple of parties and invite (Als tackle) Josh Bourke, (defensive lineman John) Bowman and all the guys.
"I think that would be great. They probably wouldn't come but I'd invite them anyway."
Note to readers: This is a corrected story. A previous version had Stewart appearing in his ninth Grey Cup instead of his eighth.