The MLB decision-makers under the most pressure heading into 2026

Opening Day optimism is here. Behind the scenes though, a handful of MLB decision-makers are entering 2026 with real pressure. It's the kind tied to job security, legacy and whether their vision actually works. Let’s dive into the most pressurized situations heading into 2026.

New York Yankees: Brian Cashman

• The situation: A roster that closely resembles the 2025 team, which lost in the ALDS
• What's at stake: First World Series title since 2009

The Yankees are running it back with largely the same roster as last season. Trent Grisham returned after accepting the qualifying offer. Cody Bellinger re-signed on a five-year contract after an offseason standoff with the front office. New York traded for Marlins pitcher Ryan Weathers in exchange for four prospects, but that was about it for new additions.

“We have really good players, a collection of really talented players. It’s not the same roster,” Cashman said, via the New York Daily News. “I would differ there. We have some players, at some point, returning from the IL that are important players, Gerrit Cole being one of them. But we had some additions from the second half that got their feet wet with the Yankees, some with failures or success. But they’ll now be in a position to join us with their feet on the ground and getting their sea legs under them — with a manager, too, learning how to utilize these guys, where they slot, and everything else. So I disagree it’s the same team running it back.”

The Yankees should be a playoff team once again. But for a big-market team, especially one with such high expectations, getting to the playoffs shouldn’t be enough. And it’s fair to wonder if Cashman and the front office really maximized their World Series chances.

Pittsburgh Pirates: Ben Cherington

• The situation: A much-improved roster with elite young talent
• What’s at stake: First postseason berth since 2016

This is the most talented roster the Pirates have had in quite some time. Numerous agents and rival executives have praised the job that Cherington did this winter, lauding his trade to acquire Brandon Lowe from the Tampa Bay Rays in particular. They also signed Ryan O’Hearn to their first multi-year contract since Ivan Nova way back in 2016. They strongly considered Marcell Ozuna all winter, and as he lingered on the market, eventually signed the veteran slugger to a one-year contract.

Expectations are different now in Pittsburgh. With their offseason spending spree, as well as having Paul Skenes in the rotation and Konnor Griffin’s debut looming, playoffs are the new standard in Pittsburgh. And Cherington has positioned the Pirates to make their first postseason appearance since 2016.

Boston Red Sox: Craig Breslow

• The situation: A deep pitching staff, but is there enough hitting?
• What’s at stake: More criticism if offense struggles without Devers, Bregman

Immediately after the Rafael Devers trade last June, my Twitter mentions looked something like: This is the Mookie Betts disaster all over again. There’s no way the Red Sox just did that. What is Craig Breslow doing? What’s next?

What followed was Boston further bolstering its rotation, signing Ranger Suarez on a five-year, $130 million contract and trading for Sonny Gray. They did not re-sign Alex Bregman, though. They had interest in Kyle Schwarber, but the industry expectation was always that he’d end up in Philadelphia. They had strong interest in Bo Bichette, who eventually signed with the New York Mets. They ultimately traded for third baseman Caleb Durbin, an emerging young player in Milwaukee, and signed Isiah Kiner-Falefa to a one-year contract.

The Red Sox are banking on their young, homegrown talent, especially Roman Anthony, taking the next step. We’ll see if it’s enough. If not, Breslow will be scrutinized. And it could force him to act aggressively at the deadline.

San Francisco Giants: Tony Vitello

• The situation: A roster built to win now, with first-time Major League manager
• What’s at stake: Silencing doubters after being hired away from University of Tennessee

The Giants hiring Vitello as manager was met with scrutiny around baseball, with many noting how he's never managed at the big-league level and the difficulties of moving from college straight to the Majors.

Throughout spring training, players praised Vitello and his energy. Ron Washington, a long-time MLB coach and manager, wasn't shy about being complimentary. President Buster Posey, a franchise icon, went all-in on Vitello and believes in the first-year manager to lead the organization back to winning ways. It helps that he has two former managers on his staff in Washington and Jayce Tingler to help with the transition, and a talented roster headlined by Rafael Devers and Willy Adames among others. But all eyeballs will be monitoring Vitello closely in San Francisco throughout the 2026 season.

Atlanta Braves: Alex Anthopoulos

• The situation: Hoping to get back to playoffs, but dealing with roster with plenty of questions
• What’s at stake: Potentially missing postseason in consecutive seasons

Anthopoulos is one of the best executives in baseball. His resume speaks for itself, and there is a reason the Atlanta Braves have trusted him since 2017 to lead their franchise.

But the Braves did not make the playoffs last season and were eliminated in the Wild Card round in 2024. They did not trade some of their assets at the deadline last season with the goal of contending in 2026. They had a need for another starting pitcher, especially with Spencer Schwellenbach and Hurston Waldrep dealing with elbow injuries, and did not sign an impact starter. And now with Spencer Strider set to open the season on the Injured List with an oblique strain, failure to address the rotation will draw even more criticism. 

Lucas Giolito remains unsigned, so there is a chance to fix this. But Anthopoulos may be forced to be aggressive in pursuing starting pitching via trade midseason.

New York Mets: Steve Cohen, David Stearns

• The situation: A roster built to win now, with World Series aspirations
• What’s at stake: Further frustrating an already “annoyed” Cohen if no World Series

After Steve Cohen bought the franchise in 2020, he declared that it would be disappointing if the Mets didn’t win a World Series in 3-5 years.

Well, the Mets have not won a World Series since Cohen bought the team, and the furthest they’ve advanced in that timeframe is the National League Championship Series in 2024. They missed the playoffs in 2025 after signing Juan Soto to the largest contract in professional sports history, prompting Cohen to say in spring: “I’m absolutely annoyed. Every year it goes by, I get frustrated. I’m really committed to this team. I know how much the fans care. I know we’re celebrating the 40th anniversary of 1986, and that’s just too long.”

New York underwent a significant roster makeover this winter, with Pete Alonso, Brandon Nimmo, Edwin Diaz and Jeff McNeil all off the team. The roster now includes Bo Bichette, Freddy Peralta, Marcus Semien and Luis Robert Jr., Devin Williams and Luke Weaver. Those changes signaled Cohen’s belief in David Stearns to run the Mets and get them back to the World Series. For Cohen’s sake, Stearns better be right. Otherwise the World Series drought will continue.

Toronto Blue Jays: John Schneider

• The situation: Following up a season that came within inches of winning World Series
• What's at stake: Can Toronto climb the mountain?

The Blue Jays were this close to winning the World Series last season. They’ve been criticized throughout the winter for failing to sign Kyle Tucker and, frankly, I think that’s misguided.

Toronto had a strong offseason. They signed Dylan Cease to anchor the top half of their rotation. They signed Max Scherzer, Cody Ponce and Kazuma Okamoto and acquired outfielder Jesus Sanchez in a trade with the Houston Astros. They have the proper pitching depth and talent to navigate the 162-game regular season and another deep postseason run. Losing Bichette hurts, of course, but the Blue Jays are well-positioned headed into 2026. And manager John Schneider and executive vice president of baseball operations and general manager Ross Atkins, the architects behind this Blue Jays team, were extended days before Opening Day.

Atkins has assembled this roster. Now, it’s up to Schenider to maximize it once again.