OTM Roundtable: What matchup do you want to see?

The Red Sox are mired in a tight wildcard race in which five teams fighting for two spots are separated by four games. As we speak here Friday morning, the Red Sox and Blue Jays are tied and hold the top two spots, with New York trailing by a half-game, Oakland by three games, and Seattle by four. For this week’s roundtable, I asked which matchup everyone would like to see the most, and which they’d like to see the least.

Scott Neville

I am rooting for a Red Sox-Blue Jays wildcard game at Fenway. Now, I am absolutely more scared of the Blue Jays than the Yankees. That said, I would find it very amusing if the Yankees didn’t make the playoffs and finished in fourth place in the American League East after being heavy favorites to win the division. Also, the Blue Jays lineup is superb, but they don’t have anyone like Gerrit Cole to start the game. I feel strongly that in a wildcard game the Red Sox could hold the Blue Jays lineup with a combination of Sale, Whitlock, and whoever is hottest in the bullpen at that point. Houck? Richards? Ottavino? Meanwhile, the Red Sox have “handed Robby Ray his lunch” already, as Eck would say, and can destroy that bullpen in a one-game do or die situation.

The least enticing matchup would be Red Sox-Athletics or Red Sox-Mariners, those games just don’t get the juices flowing like the AL East matchups would.

Keaton DeRocher

Normally I’d say Red Sox -Yankees for the #Drama, but to deny Vladimir Guererro Jr. and Bo Bichette the chance at playoff excitement seems rude. Red Sox-Blue Jays is my vote. It’s still a very exciting divisional matchup, Chris Sale vesrsus Robbie Ray would be a delight to watch go toe to toe, and of course the added bonus of sad Yankee fans on the outside looking in. I feel more confident the Red Sox could beat the Yankees in a one-game playoff — like, way more confident — but that one game with Toronto would be super exciting and I’d happily watch those young Toronto stars make a deep run, should the Red Sox fall.

Michael Walsh

A good old-fashioned Red Sox-Yankees matchup would be my best-case scenario for the wildcard. The atmosphere in Fenway Park/Yankee Stadium would be unmatched in a winner-take-all game between two of the biggest rivals in baseball history. The matchup I want to see the least is Blue Jays-Yankees, mostly because I’d be bitter if the Sox are left out. However, with the Blue Jays on an absolute tear, both the Sox and Yanks are going to need to step up in a big way to make the wildcard rivalry game a possibility.

Steven Brown

The Wildcard race has clearly been a hot topic recently as the Blue Jays have seemingly surged into the favorite position. The team has been phenomenal over the past month and has a very real chance of running away with the No. 1 spot if it continues winning as many have seen as of late. The way things are shaking out, the latter of the two spots will be the ultimate pinnacle of who’s advancing to the playoffs, and given the numbered days left in the month of September, every single game is a must-win. I believe the Red Sox will ultimately fight its way into contention. Through the great times (the first half of the season) and the worst of times (a COVID outbreak in the midst of a downward spiral), Boston has found a way to remain competitive with the rest of the league.

I ultimately believe that the Blue Jays will end up facing the Red Sox in the Wild Card game this postseason. The Yankees have made a steady comeback, yes, but the team has also been more painful to watch to a devoted New York fan base than the Red Sox over the last few weeks. The match-up that I would least like to see is also, unfortunately, the one I am predicting. While a Toronto-Boston game would be an exciting divisional matchup for a Wild Card, most people would likely prefer to see Boston take on New York. While the narrative would obviously be one of anger and disgust should Boston lose, the excitement and buzz surrounding a team that had just beaten its divisional foe would seemingly ignite the Red Sox into an energized and fearless team with a focused state of mind.

Photo by Mike Stobe/Getty Images

Bayleigh Von Schneider

I think the team I’d want to see the Red Sox face in a one-game playoff is easily the New York Yankees. Ideally, a perfect world would gift the Red Sox the opportunity of homefield advantage against a team like the Athletics or Mariners, but the chances of that happening are slim to none! So, give me Gerrit Cole versus either Nate Eovaldi or Chris Sale, and hopefully it is at Fenway. The Sox have beaten Cole handily this season, and there’s no reason they cannot do it again. The team I’d least want to face is the Blue Jays. The Blue Jays have an elite offense, an offense that has already creamed the Red Sox this season. The Jays are hot, and facing a hot team in a one-game playoff could be detrimental to the Red Sox, and the hopeful success of sneaking into the ALDS.

Mike Carlucci

Although it’s an AL East match-up, and technically something of a rivalry, I want to see the Red Sox and Blue Jays in the Wild Card game. Chris Sale (or Nathan Eovaldi) against Vlad Jr. with the season on the line? Sounds exciting to me! Am I confident the Sox win this game? No. Note I feel like I’m picking the toughest opponent. But that’s somewhat minimized in a one-game series rather than over five or seven. Even bad teams can beat great ones in baseball on any given night. But we’ve done the thing with the Yankees and the Mariners aren’t as exciting as team to play.

Since I defined the Sox match-ups as the ones I want, and their priority by opponent, the Wild Card match-up I’d least like to see is Yankees versus Blue Jays. If the Red Sox aren’t in that game I want the Mariners end their playoff drought and advance from the Wild Card round. I don’t think they can beat the Sox, Yankees, or Jays, but in one game? Sure let’s ride Mariners fans! Otherwise, give me Vlad.

Brendan Campbell

The Wild Card matchup I am most rooting for is the Red Sox hosting the Blue Jays at Fenway Park. The Wild Card matchup I least want to see would be either the Athletics or Mariners taking on the Blue Jays or Yankees on the road.

The Red Sox matching up against the Blue Jays at home in the Wild Card game would mean they were able to hurdle past their two division rivals over the final two-plus weeks of the regular season for the right to host the pivotal one-game playoff. It would also set up an intriguing pitching matchup – presumably between Nathan Eovaldi and Robbie Ray – on Tuesday, October 5. As a reminder, the Red Sox have never played in the Wild Card game since its inception in 2012.

If the Athletics or Mariners were to travel to Toronto or New York to take on the Blue Jays or Yankees in next month’s Wild Card game, that would mean the Red Sox slipped up and faded away at the finish line. A Red Sox-less Wild Card game in early October would also mark the third straight year in which Boston failed to qualify for the postseason.

Avery Hamel

I think at this point, I’d most be looking forward to a Red Sox/Blue Jays wildcard matchup. From a fan perspective, it would be amazing, and the Jays more than deserve it. From a Red Sox fan’s perspective, it scares the living #&*% out of me. It’d be an obviously entertaining matchup, and I’d rather the Jays make the ALDS than the Yankees, but it would be a tough matchup. When healthy, I believe the Jays have one of the best lineups in the MLB, and both their starters and relievers have shown what they’re capable of in the past months. Alas, it seems the Mariners are out of contention, and I think an AL East title bout Wild Card game would be the most entertaining option this year, and ideally, that team ends up being Toronto.

Stephen Thompson

As a fan of baseball, I am craving a one-game Yankees-Red Sox playoff. Could you imagine what Fenway — or Yankee Stadium, for that matter — would look like on the night of a single, winner-take all contest between two ancient rivals? Sign me up. Toronto, Oakland and probably even Seattle, would make for some intense playoff environments, but they wouldn’t provide the same spice as a matchup with New York.

Even from a more self-interested perspective, it’s the most favorable matchup for the Red Sox of the remaining contenders. Boston is 10-6 vs. the Yankees this season and 17-15 combined against Toronto, Oakland and Seattle. The Red Sox would have the starting pitching advantage, even against Gerrit Cole, who only has one win vs. Boston this season and it was a 3-1 victory called after six innings. I want the atmosphere that matchup would bring and I’m confident the Red Sox would win.

Bob Osgood

What I want to see and what I expect to see are greatly different questions. The Toronto Blue Jays have been absolutely terrifying for weeks, winning 16 of their last 19 games. I expect to see the wild card game go through Ontario, with the winner of the Red Sox vs. Yankees three-game set next weekend at Fenway likely deciding who the road team will be at Rogers Centre.

In terms of what I want to see, nothing would be a greater spectacle than a Yankees vs. Red Sox one-game playoff at Fenway Park on a Tuesday night in October. Chris Sale versus Gerrit Cole? Nick Pivetta vs. Nester Cortes Jr.? I don’t care. Get me one-game playoff revenge for Bucky Dent in 1978, and get my ticket agent on the line as soon as possible. And if the game is in the Bronx, yeah I’ll probably watch that too.

Brady Childs

I want to bury the New York Yankees in the ground and get Aaron Boone and possibly Brian Cashman fired. How cool would that be!!! Aside from that, I’m terrified of what the Jays’ offense could do in a single game against any pitcher on this staff, including Chris Sale. Order of preference goes something like Yankees, Mariners, the A’s, and the Jays. For as wacky and inconsistent as this team is, I think they have a good shot against any one of the Yanks, M’s and A’s. The Jays, as hot as they are now, are not a team I want to mess with. Of course, I don’t get to pick the opponents and it’s looking more and more likely like Toronto will have home field, leaving whoever faces them with a tough mountain to climb.

Jake Devereaux

The matchup I’m most rooting for is Red Sox vs Blue Jays. First of all, the Blue Jays are an incredibly fun lineup to watch. They absolutely mash and they look like they have fun doing it. Secondly, if the Blue Jays and Red Sox are in that means the Yankees are already scheduling tee times—this warms my heart. I also have a suspicion it may force the Yankees to make some larger changes in the off-season that could take them out of the running for a few years. Lastly, it will give Eovaldi or in my opinion Sale the opportunity to have a huge moment where one of them shuts down arguably the best offense in baseball in order to advance to the ALDS.

Matt Collins

I feel like I’m losing my mind with these answers. The objectively correct answer for most preferred matchup has to be Red Sox-Mariners. Seattle could obviously win that game — they won one against the Red Sox just a few days ago — but they seem to definitely be the worst team in the mix. I would like to see the Red Sox play the team they have the best chance of beating, thank you very much. And I would least like to see them play the Blue Jays. (Which isn’t what I asked but is what I meant to ask!) I like most everyone on that team, and would be rooting for them in just about any other matchup. But they are also, to me, clearly the best team in this mix. I would not like to see the Red Sox play the team they have the worst chance of beating, thank you very much.