The Biggest Question Facing Every 2026 MLB Contender

With major league teams reporting to Spring Training this week, it’s a good time to ask the biggest questions for postseason contenders in 2026.

Toronto Blue Jays

Can Trey Yesavage be that effective again over the entire season?

Yesavage famously shot up the Jays’ minor-league system in 2025, ascending from Class A to the World Series. He had an 11-strikeout and a 12-strikeout performance in the postseason, but he’s still just nine appearances into his major league career.

Toronto has significant question marks across the rest of the pitching staff, but many of them can be papered over if Yesavage delivers a great first full season.

New York Yankees

Will ace Gerrit Cole regain his Cy Young form?

They have one of the deeper starting rotations in the league — one that can override questions about their position players and bullpen.

But the only way they’ll win the World Series for the first time in 17 years is if Cole is pitching like an ace in October at age 35, coming off Tommy John surgery.

Boston Red Sox

Will the offense score enough runs to make this a playoff team?

The front office had a tough offseason, letting go of Alex Bregman and adding more starting pitching when bolstering the lineup seemed prudent.

They will have Roman Anthony for a full season, and Willson Contreras will help. But they’ll also need Trevor Story to repeat his renaissance season and several other hitters to perform at higher percentiles than they did in ’25.

Baltimore Orioles

Did they add enough pitching?

Pete Alonso and Taylor Ward can slug, but the O’s had deeper needs on the pitching staff, particularly in the rotation.

They flirted with free-agent left-hander Framber Valdéz but bowed out of the bidding. They did make an intriguing trade for right-hander Shane Baz, though he’s still a reclamation project.

Otherwise, the Orioles are rolling with the starters they had at the end of ’25. It’s all too risky.

Seattle Mariners

Are they still a hitter or two short?

They added Brendan Donovan to play third base (or possibly second), which is fine — but still leaves something to be desired for an offense that finished 10th in runs scored.

The M’s should make the playoffs again if the starting pitchers repeat their ’25 performance, but they won’t make the World Series without better batting.

Detroit Tigers

Was not addressing the lineup an offseason mistake?

They waited out Valdéz and old pal Justin Verlander before making late moves to improve the rotation.

But everyone remembers Detroit’s infuriating inability to score runs in the postseason.

They essentially have the same lineup again.

Chicago Cubs

Who is the real Pete Crow-Armstrong?

A fantastic breakout season faded late when he hit .216/.262/.372 in the second half, followed by 12 strikeouts in 29 postseason plate appearances.

What if Crow-Armstrong’s fade is a harbinger of bigger struggles?

Los Angeles Dodgers

Can Shohei Ohtani win NL MVP and Cy Young in the same season?

Being the best hitter and pitcher in the league simultaneously is about the only thing Ohtani hasn’t accomplished yet.

He’s far enough removed from Tommy John surgery that he won’t be restricted in his innings.

This may be his best chance to do it.

New York Mets

Even with so many new faces, did they change enough of them?

They have at least five new hitters in the lineup: Bo Bichette, Jorge Polanco, Marcus Semien, Luis Robert and rookie Carson Benge.

Freddy Peralta joins the starting rotation, and Devin Williams plus Luke Weaver headline a revamped bullpen.

But with Alonso gone and Francisco Lindor now dealing with a hamate injury, the Mets don’t feel like locks to make the playoffs coming off 83 wins.

Milwaukee Brewers

How much better can Jackson Chourio get?

They proved they can make the postseason with a deep roster of solid players.

But to become true World Series contenders — assuming that’s ownership’s goal — someone like Chourio needs to make the leap from good to great.

He may have the best chance on the roster to become a postseason difference-maker, along with right-hander Jacob Misiorowski.

Philadelphia Phillies

Will they hit enough after the top of the order?

Team president Dave Dombrowski irritated Bryce Harper by implying he was diminished as a hitter — and it wasn’t Harper’s best season.

But he was still one of the three best bats in the lineup, along with Kyle Schwarber and Trea Turner.

The real issue was the rest of the lineup, and aside from adding Adolis García, it wasn’t significantly addressed.

San Diego Padres

Are they about to tear up the roster?

Manny Machado’s salary is set to spike, and Fernando Tatís Jr.’s production hasn’t fully rebounded since his PED suspension in ’22.

That’s a lot of resources tied to two players on a roster that may have already peaked.

They’ve also struggled to find managerial stability, and it’s the final season of A.J. Preller’s contract.

Cincinnati Reds

Can Suárez hit 60 home runs playing 81 games in Cincy?

He finished with 49 in ’25 and now returns to one of the most homer-friendly parks in baseball.

Cleveland Guardians

Why does anybody pitch to José Ramírez?

A couple of young hitters appear to be developing, but no one else in the lineup is particularly menacing.

Ramírez produces at an elite level — nearly unprotected — and still finds ways to do damage.