Matt Smith/CFL.ca
TORONTO — It’s hard being a three-seed in the Grey Cup Playoffs.
Winning as many as three road games en route to a championship is the toughest path possible, a task facing both the Winnipeg Blue Bombers and Edmonton Eskimos this season.
The Bombers must go into McMahon Stadium and beat the defending Grey Cup Champions, then, if successful, travel to Regina to take on a well-rested Riders team that’s lost only five times in 2019.
If you’re Mike O’Shea, the good news is you’ve taken two of three games against Calgary this season, and defeated the Riders 35-10 in the Banjo Bowl.
Three-Seeds to Win the Grey Cup (Since 1945): 
Edmonton 2005
BC 2000
BC 1994
Saskatchewan 1989
Montreal 1970
Going east as a result of the crossover, the Eskimos’ task is equally daunting, traveling long distances to face high-octane offences of Montreal and Hamilton, with hopes of returning to their closest rival’s stadium in Calgary for the finale.
The Eskimos hope that Trevor Harris, who’s only made one start since being injured on Sept. 7, can shake off the rust and return to old form, as the Esks try to become the first crossover team in CFL history to play for a Grey Cup.
The last time a three-seed won a Grey Cup, Ricky Ray was the quarterback of the Eskimos in 2005. There’s a reason that dating back to 1945, only five teams have accomplished the feat.
Who has the better chance to make history? More in the Weekly Say.
Which three-seed has a better chance at a Grey Cup?
Esks running backs C.J. Gable and Shaq Cooper look to lead a deep run through the East (The Canadian Press)
Marshall Ferguson: Edmonton. Trevor Harris knows how to navigate the Eastern waters and has so much talent around him.
Matthew Cauz: I’m going with Winnipeg. Edmonton has fewer questions at quarterback but Winnipeg had a more impressive overall season. Also I just don’t see Hamilton losing at home.
Don Landry: Winnipeg is more likely to run the table than Edmonton. The toughest road win in the CFL in 2019 is Hamilton and based solely on that, the Eskimos have the tougher assignment. As well, it’d be a surprise should the Eskimos win in Montreal. The Bombers have, potentially, two very tough road games ahead of them as well but they are a more complete team than the Eskimos, and have a better chance to win consecutive games on the road.
Jim Morris: Neither actually. But of the two I would pick Winnipeg. I don’t see anyone beating Hamilton in the East. Winnipeg has beaten the Stampeders this season. Beating the Riders in Regina is hard but not impossible.
Chris O’Leary: I think this is unlikely on both sides. A crossover team has never made it to the Grey Cup game and this Esks team hasn’t beaten a winning team yet this year. It’s hard to be sold on the Bombers based off of one game with Zach Collaros at QB and they’re up against history too. The 2005 Esks are the only recent team to win all three road games to win a Grey Cup. The Bombers are the more complete team though, so I’d lean toward them.
Jamie Nye: Winnipeg has defeated the Riders and the Stamps this season (albeit only at home). They also have a less rigorous travel schedule and the run game to win and the defence to take over a game. Oh, they also have a return game that is one of the best in the league and a top kicker as well. The Bombers have everything going for them if they get good quarterbacking. Edmonton could beat Montreal but Hamilton over matches them across the board.
Who is the player to watch in the 2019 playoffs?
Riders QB Cody Fajardo was named CFL.ca’s player to watch in the post-season (Matt Smith/CFL.ca)
Ferguson: Brandon Banks. Nobody can change a game quicker and his 2014 Eastern Final at home against Montreal could be getting an encore.
Cauz: I’ll go with the quarterback of the best team in the CFL Dane Evans.
O’Leary: Andrew Harris. He has plenty of motivation to go out and win the one thing that he can’t be excluded from this year and if their passing game struggles against Calgary, he may have to literally carry the load for his team. Honourable mention: Dexter McCoil in Calgary. He has difference maker written all over him.
Nye: Dane Evans and Cody Fajardo. Sorry, I may be cheating but these first year quarterbacks will be interesting to watch to see how they handle the pressure of all of a sudden being the favourites to win out of the West and the East. Can they perform in the playoffs like they have in the regular season?
Landry: Eugene Lewis is my player to watch. It seems to me that he has been getting a little bit edgier as the season has wound down, a little more pumped. He might be about to go off.
Morris: So many choices. Cody Fajardo’s health dictates if the Riders have any chance of advancing to the Grey Cup. During the season, there always was next week. Now in the playoffs it’s win or go home. It will be interesting to see how a quarterback, who started the season as a backup, handles the pressures and expectations of playing in Saskatchewan.
Which player, coach or GM is under the most pressure in the post-season?
Despite returning to the playoffs, some whether wonder the Esks have underachieved in 2019 (The Canadian Press)
Nye: Jason Maas. I feel like his job is on the line if he doesn’t get the Eskimos to the Grey Cup. I don’t even know if a trip to the Eastern Final will be enough after another letdown season, especially after such a strong start.
Landry: Edmonton head coach Jason Maas is under the most pressure. Had already been talk about possible off-season changes there, should the Eskies go splat in the playoffs. Now, with Rick Campbell out there as a free agent, the pressure intensifies.
Morris: I would say Jason Maas. I think his fate might be sealed already, but a long run in the playoffs would make decisions in Edmonton that much more complicated.
Ferguson: Jason Maas. Fair or not, a loss in Montreal feels like it might be his final in Edmonton.
O’Leary: Jason Maas. I think he needs a win on Sunday in Montreal to secure his future with the Esks. Fans in Edmonton have been restless over him the last couple of years and Rick Campbell’s sudden availability has those same fans wanting Campbell back where he grew up.
Cauz: Jason Maas. Two underwhelming seasons with a fully healthy Mike Reilly and 13 games from Trevor Harris yet the team has a losing record over the past two years.
