Last offseason, the Pittsburgh Pirates reportedly tried making some free agent splashes by going after Kyle Schwarber and Josh Naylor. In the end, they fell short, with both players returning to their clubs.
However, that rumor signaled a potential shift in the Pirates’ trend in spending. They are making more of an effort to bring in some free agents and spend some money. Just how much they are willing to spend remains to be seen. Pittsburgh finished about .500 for the first time in eight years in 2026. That was somewhat surprising given the struggles of ace Paul Skenes.
This figures to be a big offseason in the Steel City. Kerry Miller of Bleacher Report predicted that the Pirates are going to make a free-agent splash for next season.
Pittsburgh Pirates Predicted To Sign Jazz Chisholm Jr. in Free Agency
The Pirates have an interesting decision to make this offseason. Do they give Brandon Lowe a qualifying offer and he returns for one year at $23.15 million? Acquired from the Tampa Bay Rays last winter as part of a three-team trade, Lowe was good for Pittsburgh in 2026.
However, if they let him walk, Miller believes that Pittsburgh will sign New York Yankees second baseman Jazz Chisholm Jr.
“With Lowe now headed for free agency, they need to add an infielder if they’re going to chase this sudden surge of competence,” wrote Miller. “It wouldn’t be a long-term, nine-figure monster of a deal.”
Pittsburgh has extended both young superstar Konnor Griffin and Bryan Reynolds for over $100 million. So breaking the bank with a big long-term deal isn’t going to be in the cards for Chisholm Jr. and the Pirates. But Miller laid out a deal that would work for both sides.
“But what if Dec. 1 (AKA Lockout Eve) rolls around and Chisholm—after discovering the market doesn’t think he’s nearly as valuable as he thinks he is—gets a phone call from a 412 area code with an offer for $30M for one season?,” wrote Miller.
As Miller pointed out, the potential looming lockout is something that players and front office personnel need to keep in the back of their minds. That is going to make for an interesting November after the World Series ends.
Jazz Chisholm Jr. Expected To Part Ways With New York Yankees
Chisholm Jr. and the Yankees going their separate ways would not be surprising this winter. Adding Chisholm Jr. to a Pirates roster with some young talent and coming off a winning season would add intrigue to the 2027 campaign.
His numbers took a hit in 2026 with the Yankees, slashing just .231/.312/.399 with 15 home runs and 55 RBIs. However, he is one year removed from a career-high 31 home runs and 80 runs driven in in 2025. The Pirates would sign up for that type of production.
Despite Pittsburgh posting a winning season in 2026, the National League Central Division goes through the Milwaukee Brewers. The Chicago Cubs are not too far behind. If Pittsburgh is going to close the gap, signing Chisholm Jr. to a prove-it deal is something that should be considered.
Pittsburgh Pirates Predicted To Sign New York Yankees Star Free Agent Infielder