Why Ben Cherington must avoid preferred Pirates offseason pattern in 2026

Ben Cherington is returning to the Pittsburgh Pirates for another year. For better or for worse, he's getting another offseason. Given a new lease on life, there's one thing he cannot do this winter that he's done every offseason since taking over as general manager: sign a veteran left-handed starting pitcher. With so much pitching depth, the last thing the Pirates need to do is invest more of their minimal resources into more starters. They need to funnel those resources into offense.

This practice began with Derek Holland during the 2019-2020 offseason. He signed a minor league deal, but made the Pirates' rotation during the shortened 2020 campaign. The following winter, Cherington signed Tyler Anderson to a $2.5 million contract. His best signing during this routine was during the 2021-2022 offseason when he imported Jose Quintana. He then picked up the ageless wonder, Rich Hill, for the 2023 season. Prior to 2024, he signed Martín Pérez, along with acquiring Marco Gonzales via trade. Finally, in 2025, he gave Andrew Heaney a shot, which was arguably the most disastrous addition of them all.

Looking ahead to this year's free agent market, the aforementioned former Pirates, such as Anderson, Quintana, Perez, Heaney, and Hill, will all be available for pickup, provided they decide to continue their playing careers (a significant question for Hill). Steven Matz, Nestor Cortes, and Patrick Corbin all fit the sort of profile Cherington has pursued before. However, none of them present a better option than what the Pirates currently have on their depth chart.

Ben Cherington must use his Pirates resources wisely, and not spend it on an unnecessary pitcher.

Both Paul Skenes and Mitch Keller are guaranteed starting rotation spots (as long as Keller isn't dealt this offseason). Bubba Chandler and Braxton Ashcraft likely have inside tracks for spots as well. That leaves the fifth and final spot up for grabs, and there will be plenty of competition next spring in search of securing it. Mike Burrows, Johan Oviedo, and Hunter Barco are all vying for that spot. The Bucs will also get Jared Jones back sometime next season, and top prospects Wilber Dotel and Antwone Kelly will more than likely be added to the 40-man roster to protect them from the Rule 5 draft, only further improving the Pirates' pitching depth.

Even if the Pirates trade a pitcher or two this offseason, that still doesn't justify bringing in a 35+-year-old starter. Signing Cortes or Corbin on a one-year deal only fills a roster spot that could be used more efficiently. At that point, the Pirates might as well see if Thomas Harrington can figure things out at the Major League level. He is still young enough that he could find his footing and be a part of the Pirates' pitching staff in the long run, unlike a veteran lefty on a one-year contract. If Cherington desperately wants a lefty in the rotation, then he should give Barco the inside track to the final rotation spot.

Fans know the Pirates' front office has very little to work with when it comes to player acquisitions. Spending a dime on an unnecessary starting pitcher is completely wasteful. The pitching staff is the team's biggest strength, and arguably the only thing they got right in 2025, and it definitely wasn't because they signed Andrew Heaney to a one-year contract. The only sort of contract they should be handing out to a starter is a minor-league deal for Triple-A depth and nothing more. Everything else needs to go toward making the abysmal offense better this offseason.