A Yankees-Red Sox showdown? The Dodgers tested from the start? What we can’t wait to see in the MLB playoffs

It wasn’t quite as chaotic of an ending as it could have been, but the 2021 MLB regular season is finally in the books. Now, playoff baseball is finally in store.

In the AL, the Boston Red Sox and New York Yankees renew their historic rivalry in what promises to be an intense wild card matchup, while the dark horse St. Louis Cardinals try to keep their surprising season going against the Los Angeles Dodgers. They’ll all be competing for the chance to join the Tampa Bay Rays, Chicago White Sox, Houston Astros, Atlanta Braves, Milwaukee Brewers and San Francisco Giants in the division series.

The 2021 MLB playoff field

American League
Wild Card: Yankees vs. Red Sox
ALDS: Yankees/Red Sox vs. Rays and White Sox vs. Astros

National League
Wild Card: Cardinals vs. Dodgers
NLDS: Cardinals/Dodgers vs. Giants and Braves vs. Brewers

Full playoff schedule and bracket

We asked Bradford Doolittle, David Schoenfield, Alden Gonzalez, Jesse Rogers and Marly Rivera for their takes on what’s looking like an exciting and competitive postseason.

Now that the playoff field is officially set, what are you most excited to see in October?

Doolittle: Not to give an overly Chicago-centric answer, but the fact of the matter is we haven’t gotten a ton of new blood in the playoffs in recent years, and the 2020 free-for-all doesn’t count. So I’m excited to see the White Sox return to the real playoffs, with home games and everything. It’s a great matchup between them and the Astros and a bit uncanny, given that it’s a World Series rematch but not in the World Series. But those are two great offenses that don’t just rely on homers to score. It should be a fun watch.

Schoenfield: This feels like the most wide-open playoff field since 2015. The last several years have been what I call the era of the superteam. We had the Cubs in 2016 (103 wins), the Astros (101 wins) over the Dodgers in 2017 (104 wins), the Red Sox (108 wins) in 2018 and the Dodgers (116-win pace) over the Rays (108-win pace) in 2020. Only the 2019 Nationals (93 wins) spoiled the party, and they had to beat the 106-win Dodgers and 107-win Astros to do it. We do have three 100-win teams in the Giants, Dodgers and Rays, but all the underdogs are certainly capable of winning it all. What I envision is a whole bunch of five-game and seven-game series full of the tension and drama that makes October baseball so compelling. Plus we get Dusty Baker finally trying to win a World Series, the Brewers searching for their first title in franchise history, the Rays trying to go two games further, Tony La Russa back in the postseason, the Dodgers trying to become the first back-to-back champion in 21 years … so many great storylines to go with all the usual drama.

Gonzalez: No disrespect to the Cardinals, who miraculously cruised to the second NL wild-card spot shortly after being counted out entirely, but a Dodgers-Giants NLDS would be fascinating on multiple levels. This is one of the most storied rivalries in baseball history, and yet they’ve never faced one another in the postseason. It’s only fitting that it happens this year, while sporting the two best records in the sport. They were separated by one game both in their season series and through the 162-game grind. The Dodgers have more talent, but the Giants match up well against them and would have the home-field advantage.

Rogers: The American League side of the postseason is fascinating. Can one of the two oldest managers in the game take their teams all the way? Is Tampa — despite the complete lack of national name recognition — good enough to get back to the World Series? Can the Yankees just mash their way to the Fall Classic? And last — but not least — how many fans will sneak trash cans into the game when Houston plays on the road?

Rivera: I am extremely excited to see what Brewers pitching can do in the postseason, and how far the Cardinals and Braves can go. I am also looking forward to seeing the Chicago White Sox back in the postseason.

And what surprises you most about this October’s field?

Doolittle: I’ll go with the fact that the Cardinals are in it. Yes, the Giants soared above my preseasons expectations for them and they are an amazing story. I mean — 107 wins? That’s crazy. But they proved the prognosticators wrong months ago. St. Louis, on the other hand, looked like a tepid, middle-of-the-road club as recently as about three weeks ago. Their reward is a road game against a team that won 106 games, but still, the fact that Redbirds have even this much of an opportunity is amazing.

Schoenfield: The Giants going wire-to-wire to clinch the NL West on the final day of the season with 107 wins. OK, they weren’t quite in first place all season, but other than three days in early September, they held sole possession of first since May 31. The Dodgers were right there all season and the Giants never gave an inch, an incredible accomplishment and credit to the depth on the roster. In an era when youth is coveted, the Giants have the oldest lineup in the league. So here’s a tip of the cap to all those old guys in the Giants lineup.

Gonzalez: Don’t let their season-long dominance make lose sight of the big picture: The Rays are a team with the fifth-lowest payroll in the sport, one that traded away one of their best starting pitchers (Blake Snell), lost another to free agency (Charlie Morton) and lost yet another to Tommy John surgery (Tyler Glasnow). And yet they finished with the best record in their league and once again sat atop an insanely competitive AL East. Yes, the Rays do this all the time. But that should only magnify their accomplishment.

Rogers: That the Giants and Rays are the No.1 seeds. Sure, Tampa Bay was coming off a World Series appearance but there was so much talent in the AL East, it was hard to picture them as the No.1 seed after Tyler Glasnow went down. As for San Francisco, that doesn’t need much explanation. A simply amazing season.

Rivera: How close the Seattle Mariners came to making it, and how weak the NL East was down the stretch.

What one thing stood out to you most on the final day of the season?

Doolittle: The maximum chaos scenario that I so wanted — maybe we all did, but I’ll just speak for myself — turned out to be a big tease. And while Red Sox-Yankees is clearly a great rivalry with reams of history behind it, the wild-card game just feels like a re-run we’ve seen way too often. Sorry, AL East fans. Even more than that: For the last two weeks of the season, I had multiple screens on multiple devices going every night, at every time slot, and I was enraptured with the stretch run. This season was a great example of the wondrous possibilities of the big league regular season. With a different seeding formula, or a more bloated playoff field, we would have been robbed of that. I hope baseball’s key decision makers do not fix what is clearly not broken.

Schoenfield: Leave the playoff system as is: Ten teams is perfect. I don’t want to see more teams in the postseason, certainly not 14 or 16, even though an expanded postseason is probably inevitable. Maybe we didn’t get a tiebreaker Monday, but we got to Game 162 with playoff spots and seeds up for grabs. The regular season still matters in baseball. Keep it that way.

Gonzalez: Dodgers first baseman Max Muncy suffering a gruesome injury to his left elbow on a close play at first base — two days after Clayton Kershaw suffered a flare-up near his pitching elbow that will likely end his season. Muncy has been one of the Dodgers’ steadiest hitters, a legitimate MVP candidate for most of the season who brings balance and patience to the middle of their lineup. Losing him for an extended period would be a tough blow.

Rogers: The resolve the Red Sox showed after getting down early to the Washington Nationals. There was bound to be one loser among the must-win teams. It turned out to be Seattle, but Boston gave Red Sox nation a scare, trailing a good portion of the day. Alex Cora will be a finalist for manager of the year.

Rivera: All the injuries that came into play, and how power offenses like the Yankees and Red Sox left a lot to be desired.

OK, looking ahead to the Wild Card games. Predict the score AND how long it will take to play Tuesday’s Yankees-Red Sox game.

Doolittle: Yankees 5, Red Sox 4 in 11 hours, 14 minutes.

Schoenfield: Edge to the Yankees because of their bullpen, although I think Gerrit Cole and Nathan Eovaldi both pitch well. Yankees 4, Red Sox 2 in 3 hours, 34 minutes.

Gonzalez: Yankees 12, Red Sox 8, in a game that lasts so long the World Series is ultimately extended into Thanksgiving.

Rogers: The final will be 6-5 Yankees in 13. The game will be the final straw for Rob Manfred. A pitch clock will be instituted the next day after the two teams play for 5:07. And that’s just for the first nine innings.

Rivera: Having done more Red Sox-Yankees games than I can count at this point, I will say 3 hours and 47 minutes. I’ll guess the final score will be 7-5. I won’t guess the winner!

What would it take for the Cardinals to send the defending champion Dodgers home in the NL Wild Card Game?

Doolittle: Gotta keep the score low. Adam Wainwright will have to be on his game of course, but the Dodgers are going to get some drives in the air and that dynamic Cardinals outfield will have to make plays. But St. Louis needs to reduce the game down to a matchup of high-leverage, late-game situations, because their bullpen matches up pretty well with that of the Dodgers. For all of this to come together, they must keep the Dodgers in the yard, which of course is easier said than done. If it’s close late, you can envision a Paul Goldschmidt and/or Nolan Arenado at-bat against Kenley Jansen flipping things in St. Louis’ favor.

Schoenfield: It’s one game between two good teams with two good starting pitchers. It’s not much more than a coin flip advantage for the Dodgers. I think a key might be Mike Shildt going with his heart and leaving in Adam Wainwright a batter or three too long. As good as Wainwright has been, the Cardinals bullpen has been outstanding down the stretch — Kodi Whitley has been dominant the past month (14 IP, 7, 0 R, 19 SO), Genesis Cabrera throws some serious heat from the left side and Giovanny Gallegos is a reliable closer. Trust those guys. Then hope you can knock a couple Max Scherzer fastballs over the fence.

Gonzalez: Max Scherzer is certainly capable of a rough outing (he has allowed 10 runs in 10 1/3 innings over his last two starts) and Adam Wainwright is certainly capable of a dominant one (he boasts a 2.34 ERA since the start of August). The key for the Cardinals might be to neutralize Corey Seager and Trea Turner near the top of the Dodgers’ lineup. They have been scorching hot of late.

Rogers: The Cardinals’ offense is night and day, producing better than they were earlier this season. They will score off Scherzer & Co. It will take Adam Wainwright’s very best to deliver a shocking blow to the reigning champions. He can do it.

Rivera: They will need Yadier Molina to have an incredible game, and they will have to ride the bats of Nolan Arenado and Paul Goldschmidt.

Which wild-card team has the best chance to win it all?

Doolittle: The Dodgers are baseball’s best team, easily the best second-place team of all-time, they are in the playoffs every single year, they are the defending champs and they have at least six future Hall of Famers on the roster. I’ll go with them. Still, the wild-card round has the Yankees, Red Sox, Dodgers and Cardinals. You can’t really have a more pedigreed list than that.

Schoenfield: The Dodgers. I don’t want to insult Giants fans and suggest the Dodgers are the best team in baseball — the Giants, after all, beat them out over 162 and also won the season series 10 to 9. Still, the Dodgers have the best run differential. They scored more runs and allowed fewer than the Giants. They play great defense, hit home runs and the bullpen — for now — looks a little more reliable than last season, when Kenley Jansen got benched as closer in favor of Julio Urias in the clinching games of the NLCS and World Series.

Gonzalez: This one is not difficult — it is, of course, the Dodgers, a 106-win team that was merely the victim of the current playoff format. Even with Kershaw out, the Dodgers can go into a postseason series with Scherzer, Walker Buehler and Julio Urias, the latter a 20-game winner. And even if Muncy misses time, their lineup is still among the deepest, most dynamic in the sport. This is also a team that has grown accustomed to the high stakes and the tense environments of October, which shouldn’t be discounted.

Rogers: It would be easy to pick the Dodgers, but if you like St. Louis in the wild card game, there is no reason they can’t build off that win as well as the success they’ve had over the month of September. There is no hotter team in the game. Isn’t that one of the criteria people talk about when it comes to the postseason? Be great or be hot

Rivera: A path through the NL seems more doable — the Cardinals or the Dodgers would both have a shot.

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