The MLB offseason is officially underway after the Milwaukee Brewers’ World Series victory this week. 

That means Pittsburgh Pirates general manager Ben Cherington has some decisions to make as he looks toward trying to return his franchise to the postseason for the first time since 2015. 

He’ll have to do so in an uncertain environment, with players and owners sharply split on what the sport’s next collective bargaining agreement should look like. The possibility of missed games – or possibly an entire missed season – in 2027 could have a major impact on the moves Cherington and his peers choose or choose not to make. 

Here’s USA TODAY’s look at the biggest questions facing the club in the months ahead. 

Can Paul Skenes be fixed? 

A bad season for the 24-year-old ace is a pretty darn good one for most pitchers. He finished 2026 with a 10-11 record, 3.82 ERA and 200 strikeouts across 32 starts. 

Those numbers don’t come close to meeting his own Cy Young-winning standard, though. Skenes’ ERA ballooned by nearly two full runs year over year, from 1.97 in 2025. Fangraphs valued him at just 4.2 wins above replacement (WAR) compared to 6.5 the year before. 

In a nine start stretch from May 17 to July 1, the team lost each time he took the mound. The Pirates went on to miss the playoffs by six games. 

Some in Pirates orbit have probably overestimated the difference Skenes could have made had he been on his game. Six games is a lot for any individual player to make up, which is reflected in those WAR numbers. 

He is nevertheless the team’s best player, and any chance the Pirates have at ending their postseason drought begins with him. Manager Don Kelly and pitching coach Bill Murphy need to find some answers, especially considering the Pirates moved on from Oscar Marin, the pitching coach Skenes had the most success with, at the end of 2025. 

That move and Skenes’ subsequent dropoff in production has justifiably raised a lot of proverbial eyebrows. So the pressure is on this coaching staff to prove that the transition was not a mistake. 

Will Brandon Lowe return? 

The veteran second baseman had one of the best power-hitting seasons in recent Pirates history with 35 homers and 29 doubles after he was acquired from the Tampa Bay Rays in a trade last December. 

He will now become a free agent, having reached the end of his final season of salary arbitration eligibility. 

The choice for Cherington, then, is pretty stark. He can pay the 32-year-old the many millions he will likely command on the open market. Or he can let his best offensive player leave for practically nothing in return. 

Each choice carries potential downsides. Of course, the lineup will be worse if he leaves in the short term. But because Lowe is well on the other side of his 30th birthday, a long-term contract extension carries significant risk of diminishing returns.  

The team has also developed some potential alternative sources of significant power. Rookie outfielder Esmerlyn Valdez hit 17 homers in 72 games in 2026. That translates to a 38-home run season over 162 games. 

Twenty-five-year-old catcher Rafael Flores Jr., meanwhile, had 11 blasts in 47 games. You wouldn’t expect him to play a full 162 games because of his position, but one could reasonably hope for somewhere between 25-30 homers from him in projecting his numbers across a full schedule. 

The anger from the fan base will be swift and severe if Lowe leaves, for understandable reasons. The Pirates have earned little benefit of the doubt with their payrolls under Cherington. One can plausibly argue that there’s plenty of money that should be available for a proven commodity like Lowe. 

The question becomes whether it’s wise to invest all of it in a single aging player. Or whether Cherington is better off spreading his risk thinner and making multiple bets with the same pile of cash if notoriously tight-fisted owner Bob Nutting approves a payroll bump for him. 

Can the bullpen improve? 

The Pirates blew 26 saves in 2026, mostly early in the year. That was the 11th-highest total in baseball and a major reason they were on the outside looking in at the postseason despite finishing fifth in runs scored. 

By the end of the season, some solutions began to emerge. Yohan Ramirez (2.86 ERA), Mason Montgomery (2.88) and Gregory Soto (3.63) all finished with reasonably solid numbers. Trade deadline acquisition Luke Weaver got off to a rocky start with the Pirates but allowed no runs in six of his final seven appearances.

This group has been a consistent problem during Cherington’s tenure. The fact that he mostly got it right by the end of the year is encouraging, but fans are correct in saying that he should have acted more aggressively early on to correct the issue. And would be justified in worrying about whether he’ll make similar mistakes this offseason. 

The pressure is now on to get this group ready to be competitive from opening day in 2027.