Pirates Facing Harsh Reality This Offseason
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PITTSBURGH — The Pittsburgh Pirates have had one of their most active offseasons in quite some time, and yet, they're still not anywhere near where they'd like to be.
The Pirates made three big time moves that saw them bolster their lineup, add two left-handed bats, outfield depth and left-handed relief pitching in their bullpen, all three things they needed this winter.
Those acquisitions have clearly improved the Pirates compared to 2025, giving fans hope that they can get back to winning baseball and make the playoffs for the first time in more than a decade.
Pittsburgh is still aiming for more additions heading into Spring Training, but them actually doing so is becoming harder and harder to do.
Pirates Struggling to Make More Moves
The Pirates can use help at corner infield or third base, another outfield addition and also left-handed starting pitching, all of which general manager Ben Cherington has said they've looked at during this offseason.
Making those additions is becoming harder, especially at third base, where the Pirates have missed out on a number of top talents.
This includes Eugenio Suárez, who just signed with the Cincinnati Reds, plus the likes of Yoán Moncada, Willi Castro, Jorge Polanco and Japanese superstar Kazuma Okamoto.
The Pirates have few remaining free agent options at third base and none of which are anywhere close to those who missed. Those that remain feature cheaper veteran options like Ramón Urías, Luis Rengifo and former Pirates infielder Isiah Kiner-Falefa.
Pittsburgh does have more options for depth in the outfield and for left-handed pitchers, but they won't come in immediate, impact players who will decide if they make the postseason or not.
Why Pirates Are Having Issues in Free Agency
The Pirates have a few issues as to why they can't add the way that fans would like them to add this offseason.
Pittsburgh isn't necessarily the most sought after destination for free agents, as they haven't had a winning season since 2018 nor made the playoffs since 2015, both the second longest streaks in the major leagues.
Free agents generally want to go to teams who are closer or are currently competing for the postseason and maybe also a Championship.
Suárez signing with the Reds isn't just about him previously playing for them or even just that Great American Ball Park is better for him as a hitter, it's that the Reds made the playoffs last year.
Kyle Schwarber was another slugger the Pirates went after and even offered a higher AAV on his contract, but he re-signed with the Philadelphia Phillies on an extra year, going back to a team that has made the playoffs the past four seasons.
The Pirates can't just make competitive offers for these top players, they have to go above and beyond, even further than just their slightly better offers they've made this offseason, if they want to get these players.
Pittsburgh is not normally a high-spending team, regularly ranking amongst the teams with the lowest payrolls, so them competing with bigger market teams in the free agent market is a difficult thing to do.
The Pirates signing of Ryan O'Hearn for two years, $29 million was their first multi-year free agent signing since 2016 and their first multi-year position player free agent signing since 2015.
It was also the highest AAV they've given to a free agent and the second highest AAV for any contract they've given out.
The Pirates need to make more deals like O'Hearn, but doing those comes from how they perform o the trade market.
Why Trade Market is Tough for the Pirates
Pittsburgh went into the trade market this offseason and landed some good talent there as well, including power-hitting second baseman Brandon Lowe, outfielder Jake Mangum and left-handed relief pitcher Mason Montgomery from the Tampa Bay Rays.
They also added prospects in outfielder Jhostynxon García and right-handed pitcher Jesus Travieso from the Boston Red Sox
Getting those players didn't come easily for the Pirates, as they parted with right-handed starting pitchers in Mike Burrows, who they sent to the Houston Astros as part of the three-team trade, and Johan Oviedo to the Red Sox.
The Pirates making those moves played a big role in them landing O'Hearn, who saw the intent from the team and saw the vision they had for this season and beyond.
Pittsburgh could use some more additions going into Spring Training and the trade market would give them, but them actually going out and doing that isn't as easy as before.
The playoffs now at six teams per each league means that more teams have a shot at making the postseason and then making a run to the World Series than ever before.
While the Pirates have playoff ambitions of their own, many MLB teams also have that desire and want players that will help them in that role.
Burrows and Oviedo leaving for the Astros and Red Sox, two playoff contenders, is what teams are looking for in MLB-ready talent that can contribute now.
The Pirates have one of the best farm systems in all of baseball, but teams don't necessarily want their prospects.
Pittsburgh can't trade away more pitching, as they already sent away two starting pitchers and still need pitchers they can rely on in 2026, which is why they're looking at southpaws for their rotation.
They also aren't going to trade star players like Paul Skenes and their top prospect in Konnor Griffin, so they have to find a team that is looking to get rid of a player that won't take one of their better players in a trade.
What the Pirates Need to Do Moving Forward
It's quite simple for the Pirates if they want to progress in the future, they need to start winning and start doing so now.
The Pirates wasted offseasons following the 2023 and 2024 seasons, where they had strong starts and even were above .500 after the trade deadline in 2024, but had collapses and fell below .500.
This led to a poor 2025 campaign that saw manager Derek Shelton dismissed in May and ended in a 71-91 record, worst in the division and fifth-worst in the major leagues.
Pittsburgh has finally had a strong offseason, but they can't just have one, they need multiple and to constantly find ways to improve the team every single year.
The best teams in baseball constantly try to find new free agents, make necessary trades and the roster moves that keep them successful.
When the Pirates were successful last decade, they relied on their best draft picks and international signings, while also making smart free agent deals and good trades to find the best talent they could afford.
This didn't result in a World Series, but it did lead to three straight postseasons and the most succesful Pirates teams of the past three decades.
Pittsburgh didn't achieve that success in one offseason, it took years to build and find the right pieces that made them a winning team from 2013-15.
The Pirates have still had a strong offseason, even with some recent misses, which should make for a much better lineup that actually supports one of the best pitching staffs in baseball.
Pittsburgh isn't yet a desirable option for free agents, but a strong showing in 2026 can put the franchise on the right track to becoming a consistent winner the rest of the decade.
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.