As the 2023-2024 offseason approaches, the pressure is mounting on Pittsburgh Pirates general manager Ben Cherington. After going 76-86 this past season, the Pirates showed signs of improvement but still finished with another losing record under Cherington's leadership. While the incremental progress is a positive sign, Cherington now faces the pivotal task of making impactful moves this winter to build on that momentum and elevate the Pirates into true playoff contention.
With fan frustration growing after six consecutive losing seasons, the time is now for Cherington to make the boldest series of upgrades since taking over as GM. This upcoming offseason has the potential to define his tenure depending on whether Cherington can construct a roster capable of competing for a postseason spot.
With one of the lowest payrolls in Baseball, the Pittsburgh Pirates must be aggressive buyers, not just bargain hunters.
The focus should be acquiring controllable young players via trade and signing productive free agents to multi-year deals. Of course, there will be some bounce back candidates they pick up, any small market team should do that. They had success this past year with Vince Velasquez before his elbow let out.
The Pirates have glaring holes to fill like a starting center/right fielder, first baseman, and pitching - both rotation and bullpen. Trades could target controllable stars at those positions. However, they also should be aggressive in Free Agency. Not just aggressive in signing, but actually entertaining legitimate veterans. I am not setting the bar for players like Aaron Nola, a guy like him will get paid more than half of the Pirates' entire payroll. Players like Teoscar Hernandez and Jordan Montgomery should absolutely be in consideration, both being in that next tier down.
Pittsburgh's window to complement its young core of Ke'Bryan Hayes, Oneil Cruz, and Mitch Keller is now. It's time to surround them with proven talent for a playoff push. If the Pirates record another losing season in 2024, Cherington's seat will get hot. The rebuild must transition to contention soon. Pittsburgh cannot continue to push competing to the next year.
A bold offseason is essential. Trading for controllable young players and signing productive free agents to multi-year deals needs to happen. Anything short of playoff contention in 2024 will be disappointing for Cherington. The time is now to end the Pirates' playoff drought.