Biggest Free-Agent Mistake Pirates Must Avoid This Winter
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PITTSBURGH — The Pittsburgh Pirates have a crucial offseason ahead of them and they must execute in free agency.
The Pirates had just their fifth winning season in the past 34 years, finishing 2026 with an 82-80 record, but were still far off from making the postseason, which they haven't done since 2015.
Pittsburgh has a strong returning cast, including a young and dominant rotation, a bullpen that improved after the trade deadline and a solid lineup that can hit for power and drive in runs.
The Pirates have reason to be optimistic for 2027, but that optimism shouldn't stop them from making necessary additions.
Pirates Can't Do the Same Offseason Before 2025
The Pirates finished 76-86 in 2024, but they were above .500 and in the National League Wild Card Race at the trade deadline.
A poor August, when they went 8-19, doomed them to another losing season, but there was optimism that they could go and build on from that season into the future, particularly following starting pitchers Paul Skenes and Jared Jones making their debuts.
The Pirates then made no serious moves that offseason, making the uninspiring free agent signings of outfielder Tommy Pham, a reunion with infielder Adam Frazier, plus southpaws in starting pitcher Andrew Heaney and relief pitcher Caleb Ferguson.
Pittsburgh's only decent move was trading for Spencer Horwitz, but he had wrist surgery and didn't make his debut until mid-May.
Pittsburgh's lack of ambition that offseason set the stage for an abysmal season, which saw terrible play and embarrassing off-the-field scandals.
It resulted in a 12-26 start and the firing of manager Derek Shelton after five-plus seasons. Don Kelly took over in his place, but the Pirates still fell to 71-91, their seventh straight losing season and 10th season away from the postseason.
The Pirates didn't just waste a season where they could've gotten closer to contention; they also failed to take advantage of Skenes winning the National League Cy Young Award.
Why That Offseason Hurt the 2026 Season
The Pirates made some great moves the following offseason, correcting the mistakes they made previously.
Pittsburgh landed second baseman Brandon Lowe, outfielder Jake Mangum and left-handed relief pitcher Mason Montgomery in a trade with the Tampa Bay Rays.
The Pirates also signed Ryan O'Hearn to a two-year, $29 million deal, which marked the first multi-year free agent signing since 2016 and the largest AAV per free agent contract in franchise history.
Pittsburgh thrived with these moves, with Lowe showing the best power of any second baseman, Mangum filling in throughout the outfield and Montgomery becoming a dominant closer.
O'Hearn was also excellent in the first half of the season, arguably snubbed from the All-Star Game, before a quad injury hurt the second half of his campaign.
The Pirates made the right moves there, but they also spent $12 million on designated hitter Marcell Ozuna.
Ozuna was terrible for the Pirates in 2026, batting .203/.286/.327 for an OPS of .613 in 70 games with just eight home runs, and they designated him for assignment in early August.
That money the Pirates used on Ozuna didn't go towards other areas of need, such as a right-handed power bat, a third baseman, or another shutdown relief pitcher.
Pittsburgh's bullpen suffered with only the addition of Gregory Soto, and if additions were made, Pittsburgh could've gotten more wins and gotten closer in the postseason race.
The Pirates were also awful against left-handed starting pitching, 18-33, and had they signed/traded for a better bat, they could've added extra victories there.
How the Pirates Must Approach Free Agency
Baseball may not happen in 2027, with the current collective bargaining agreement (CBA) expiring on Dec. 1, which will lead to the owners locking out the players.
The Pirates and the 29 other MLB teams will look to add players before the potential lockout, and it's imperative that they don't let other ballclubs get ahead of them.
Lowe is the most significant free agent in recent history for the Pirates. Re-signing him would go a long way towards showing the players and the fans that this front office is serious about the playoffs in 2027 and further.
Other additions should be made to the bullpen and third base, if possible, as the Pirates can't have another 2025 season again.
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Dominic writes for Pittsburgh Pirates On SI, Pittsburgh Panthers Pn SI and also, Pittsburgh Steelers On SI. A Pittsburgh native, Dominic grew up watching Pittsburgh Sports and wrote for The Pitt News as an undergraduate at the University of Pittsburgh, covering Pitt Athletics. He would write for Pittsburgh Sports Now after college and has years of experience covering sports across Pittsburgh.