PITTSBURGH — The Pittsburgh Pirates are in the midst of one of their most important offseasons in recent history and how they perform will give an idea on how they’ll do in 2026.
The Pirates head into the biggest week of the offseason with the winter meetings in Orlando, Fla., Dec. 8-10, where front offices across baseball talk trades and meet with agents on prospective players.
The Biggest Question for the Pirates Ahead of the Winter Meetings
Mark Feinsand and the rest of the staff at MLB.com named the biggest question for all MLB teams ahead of the winter meetings.
The biggest question they had for the Pirates is, “Will they land a big hitter?”, the most important need for the franchise this offseason.
“We’ve seen rumors of the Pirates being connected to some high-profile free agents,” they wrote. “They have some money to spend, a few obvious needs and a sense of urgency to qualify for the postseason for the first time since 2015. They also tried to add to the roster each of the last couple of winters but didn’t accomplish much. Will this offseason be different? The Pirates’ core has some talented players, but they’re going to need external additions to get over the hump. They’re talking the talk this winter. Now, they have to follow through.”
Why the Pirates Need Offensive Additions this Offseason
The Pirates were one of the worst hitting teams in 2025, with the lowest slugging percentage (.350) and OPS (.655), the third lowest batting average (.231) and the eighth lowest on-base percentage (.305).
Pittsburgh also scored the least runs (583) and drove in the least RBIs (561), both lower than the 43-119 Colorado Rockies. They also hit the least home runs (117), 31 home runs less than then second-lowest team in the St. Louis Cardinals at 148 home runs, and had the seventh most strikeouts (1,422).
The Pirates need lineup additions regardless of offense, with the left field, third base and designated hitter positions open next season.
Tommy Pham played left field for the Pirates this past season and the 38-year old was a finalist for a National League Gold Glove Award.
Aug 28, 2025; St. Louis, Missouri, USA; Pittsburgh Pirates left fielder Tommy Pham (28) scoops up a ball hit by the St. Louis Cardinals to left field at Busch Stadium. Mandatory Credit: Tim Vizer-Imagn Images | Tim Vizer-Imagn Images
Designated hitter Andrew McCutchen’s future with the Pirates is unknown after three years in his second stint with the team and at now 39 years old. The Pirates also traded long-time third baseman Ke’Bryan Hayes to the Cincinnati Reds ahead of the deadline.
Will the Pirates Actually Land a Big-Time Bat?
The Pirates have historically not spent much in free agency, which is why they have ranked in the bottom five payroll teams on Opening Day in 16 of the 19 seasons that Bob Nutting has served as owner of the franchise.
Pittsburgh also hasn’t signed a free agent to a multi-year deal since Dec. 27, 2016 in right-handed pitcher Iván Nova for three years, $26 million and a free agent position player to a multi-year deal since outfielder John Jason for two years, $8 million on Dec. 23, 2015, almost a decade ago.
The Pirates record free agent signing is when they re-signed left-handed starting pitcher Francisco Liriano for three years, $39 million on Dec. 9, 2014.
This offseason may look different, as the Pirates front office has said they understand the urgency of the situation, while other reports how them linked with free agents and tradeable players.
Pirates general manager Ben Cherington said at the general manager meetings in Las Vegas three weeks ago that they have more “flexibility” and will act more “aggressively” than in years past.
May 12, 2024; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington looks on before the Pirates host the Chicago Cubs against at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images
Team president Travis Williams echoed much of what Cherington said, while also noting that they have the resources to compete for a postseason.
Who Are the Pirates Going After?
The Pirates have had links with numerous free agents and also trade targets they will likely go after as well.
The Pirates have reportedly shown interest in free agents in Philadelphia Phillies teammates in National League MVP finalist Kyle Schwarber, who hit 56 home runs last season and catcher J.T. Realmuto, plus San Diego Padres designated hitter Ryan O’Hearn, Seattle Mariners second basemanJorge Polanco and Japanese superstars in Kazuma Okamoto and Munetaka Murakami.
Pittsburgh is also eyeing other targeted left-handed hitters from the Cardinals in Alec Burleson, Brendan Donovan, Lars Nootbaar and Nolan Gorman in a trade.
Sep 17, 2025; St. Louis, Missouri, USA; St. Louis Cardinals first baseman Alec Burleson (41) rounds the bases after hitting a home run in the first inning against the Cincinnati Reds at Busch Stadium. Mandatory Credit: Tim Vizer-Imagn Images | Tim Vizer-Imagn Images
The Pirates are also looking at two other left-handed batter trade targets in Jeff McNeil of the New York Mets and Brandon Lowe of the Tampa Bay Rays. Phillies outfielder Nick Castellanos is also a potential trade candidate.
Pittsburgh actually landing one of these players wouldn’t happen in the past, but the intent from the front office and these reports is at the very least, encouraging moving forward.