By all indications from Pittsburgh Pirates general manager Ben Cherington, the organization is once again ready to be aggressive this offseason in hopes of finally getting back to the playoffs for the first time in over a decade.

With that in mind, what part of the roster will get the most attention?

The executive made it clear that they’re looking to improve the team by any means possible, and won't limit themselves to the outfield, infield, rotation, bullpen, or anything in between.

However, there is one area where the Pirates could certainly improve, and Cherington knows it: more left-handed pitching depth.

Pittsburgh has strong options for their starting rotation heading into 2027, headlined by the All-Star duo of Paul Skenes and Braxton Ashcraft.

The issue is that the vast majority of those options are right-handed pitchers. There’s nothing to break up Pittsburgh’s top starting arms to give a lineup a different look. It’s a similar dilemma in the bullpen, too, after Mason Montgomery.

On top of all of that, there aren’t any elite left-handers making their way through the farm system who could impact the team next year. Pittsburgh’s best chance at adding a southpaw is through free agency or trade.

The stats speak for themselves, too. The 'Pirates' left-handed pitching staff has a 4.15 ERA and a 1.24 WHIP, each ranking about league average. Plus, that’s with Montgomery’s 2.88 ERA during the 2026 season.

Cherington not only understands the lack of lefties throughout the organization, but also recognizes the advantage of having more lefties in their home ballpark. 

"We see the advantage of having left-handed pitching at PNC Park,” Cherington said (via MLB.com). “We see how many left-handed hitters are in the game today. We want to put ourselves in a position to combat that as well as we possibly can.”

It’s clear: the Pirates need more lefties; there’s no other way around it. Who are some options that Pittsburgh could target?

There are actually several solid free agent options Pittsburgh could explore.

Steady veteran Robbie Ray, breakout candidate Foster Griffin, or a low-cost option such as Matthew Boyd could also be solid fits. On the bullpen side. AJ Minter or Tim Hill could fill the need, too. The Pirates also shouldn’t forget about bringing back one of their own free agents, Gregory Soto.

The Pirates must improve in many areas to get back to the playoffs next season. However, to become a better overall, well-rounded team, addressing the lack of left-handed pitching throughout the organization is a must for Pittsburgh.

Veteran Ryan O’Hearn will still be in the mix for the Pirates in 2027. However, the team hopes to use him primarily at first base and as a designated hitter, rather than in the outfield.

This opens up another offseason need for the Pirates, with Pittsburgh’s outfield depth still thin.