Pittsburgh Baseball Now: 3 Worst Moves of Ben Cherington’s Pirates Tenure

Pittsburgh Pirates General Manager Ben Cherington faces scrutiny as he enters his eighth offseason following a 2026 campaign where bullpen instability and a failed veteran signing hindered a playoff push. Analysis from Pittsburgh Baseball Now identifies the signing of Marcell Ozuna, a failure to fortify the relief corps early in 2026, and the trade of Clay Holmes as the three most damaging moves of Cherington’s tenure.

The transition from a full-scale rebuild to a competitive window has exposed gaps in roster construction. While the early years of the rebuild focused on accumulating young talent, recent efforts to supplement that core with veteran presence have yielded mixed results. The financial commitment to underperforming veterans and the loss of elite relief pitchers have created a ceiling for a team attempting to move from "future" to "present."

Marcell Ozuna signing limits offensive output

In February, the Pirates signed Marcell Ozuna to a one-year, $12 million contract that included a mutual option for 2027. The move was intended to provide a veteran bat, but Pittsburgh Baseball Now reported the signing functioned as a “panic move” that created significant roster and lineup construction issues. Ozuna struggled throughout his tenure, batting .203/.286/.327 with eight home runs and 29 RBI across 70 games.

The impact on the win-loss column was measurable. The Pirates went 26-40 when Ozuna started at designated hitter. According to the analysis, had the team gone .500 in those 66 games, Pittsburgh would have been among the three National League wild card teams. Ozuna’s presence also contributed to the team’s struggles against left-handed starting pitching before he was released before the season ended.

Bullpen regression stalls 2026 contention

Entering the 2026 season, the Pirates added only one established relief pitcher, Gregory Soto. This lack of depth became a liability as the bullpen failed to hold leads during the first few months of the year. Dennis Santana suffered a catastrophic regression, with his ERA climbing north of 6.00, while Justin Lawrence also imploded. Carmen Mlodzinski, typically an effective reliever, was utilized in the starting rotation for the first two months of the season.

The front office failed to anticipate the regression of Isaac Mattson or provide stability through early-season acquisitions. While Cherington executed helpful trades at the deadline, the window for contention had largely closed. The failure to address these needs in the offseason or early in the campaign resulted in numerous winnable games slipping away.

Clay Holmes trade yields zero return

One of the most enduring errors of the Cherington era remains the trade of Clay Holmes to the New York Yankees in exchange for Hoy Park and Diego Castillo. Neither return asset provided long-term value; Park appeared in only 67 games between 2021 and 2022 before being designated for assignment, and Castillo was similarly DFA’d in 2022.

In contrast, Holmes evolved into a two-time All-Star closer for the Yankees, helping the team secure the 2024 American League pennant. After leaving New York, Holmes transitioned to a starting role with the New York Mets, posting a 12-8 record with a 3.53 ERA in 2025. He continued to provide value in 2026, splitting time between the Mets and the Chicago Cubs with a 3.29 ERA across 18 starts. The Pirates failed to unlock the upside that multiple other organizations later utilized.

As Cherington enters his eighth offseason, the focus shifts to whether the front office can balance the pursuit of young talent with the precision required for veteran acquisitions. The gap between the Pirates' current state and a championship roster depends on the ability to identify elite relief pitching and avoid high-priced, low-output contracts.

Disclaimer: The insights provided in this article are for informational and entertainment purposes only and do not constitute medical advice or sports betting recommendations.