Who's Facing the Most Pressure in September?

September is already here, which means it's time to take a look at the pressure gauge for the last few weeks of the season.
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September is here, and the pressure is cranking up for first-place clubs, World Series favorites, MVP candidates, the commissioner and the list goes on. SI's MLB experts weigh in with who they think is facing the most pressure as the calendar flips another page.

Tom Verducci: Dodgers and Clayton Kershaw

It’s been a long time since one team established itself so far above the other 29, as the Dodgers have done. So there’s pressure right there. And Kershaw knows himself he needs a legacy game if not an outright World Series championship to quiet the talk about his postseason struggles.

After he gave up homers to Anthony Rendon and Juan Soto to blow a lead in NLDS Game 5 last year, Kershaw admitted, "Everything people say is true right now about the postseason. I understand that.”

Kershaw’s reputation is still a hunk of wet clay. He can still shape the postseason narrative. When he takes the ball for his first postseason start, the baseball world will be watching—maybe closer than for any other pitcher this October.

Stephanie Apstein: Dodgers

The Padres made a push at the trade deadline, but the answer is still the Dodgers. Resurgent but aging ace Clayton Kershaw is 32 and has a 1.80 ERA. $365 million man Mookie Betts has an OPS of .991. L.A. has the best run differential in baseball—by 50%. And it will all be for naught if the team doesn't win the World Series for the first time since 1988. The Dodgers have been the best team in baseball, or close to it, for the last three years but have nothing to show for it. They have done an impressive job of keeping their window of contention pried open, but eventually, you have to deliver in October. Unfortunately for L.A., this is a tough year for that: The first round is a best-of-three series, which is little better than a coin flip. 

Emma Baccellieri: Twins

They're still probably the best team in the AL Central, but after a six-game losing streak, they've now slid out of first, without any reinforcements added at the deadline. In a normal season, of course, "six-game losing streak" doesn't typically mean much at all—but this is not a normal season. As a result, Minnesota's now in a somewhat delicate situation. If the Twins bounce back quickly to start September, this last week will register as just a blip, and they'll be back in business. If they don't ... it could look a lot trickier.

Connor Grossman: Rob Manfred

It appears the regular season will reach its planned conclusion this month. Phew. Now comes the hard part. Rob Manfred and his lieutenants must craft as fool-proof of a postseason bubble plan as they can to ensure every October game is played. That's when the vast majority of the money will be made for teams this year. That's when the most eyeballs will be on the sport. That's when everything needs to go right. Good luck.

Matt Martell: Yankees

The Yankees are feeling the heat right now. They have one win this year against the first-place Rays and their roster again has been decimated by injuries. This was supposed to be the year New York steamrolled through the 60-game season and won its first World Series since 2009. If the Yankees cannot get healthy and start rolling by the end of September, 2020 will be a major disappointment.

Michael Shapiro: Yankees and Dodgers

It’s been over a decade since the Yankees’ last World Series appearance, but the combination of youth and eight more years of Gerrit Cole diminishes the pressure to a degree. The Dodgers don’t necessarily have that luxury. Clayton Kershaw and Justin Turner are nearing the back end of their careers. Dave Roberts hasn’t been able to get over the hump despite significant regular-season success. “World Series or bust” is a bit of an unfair designation, but it does apply to the Dodgers. There will be plenty of pressure in L.A. this October.