Pittsburgh Pirates’ Ben Cherington isn’t messing around.
Apparently, the days of Pirates’ ownership not opening up their wallet to spend on free agents are a thing of the past. As the Pirates’ general manager, Cherington is in the midst of the busiest of his seven seasons with the club. Signs of a fresh start and a new competitiveness among the players collected for the upcoming season are being mentioned by those joining Pittsburgh’s roster.
Filling needs in their bullpen, a couple of power bats, and the search for a third baseman with pop in his bat, are what Cherington has been working on, while still working the phones on efforts that he hopes will strengthen the club, beginning in spring training.
Pirates’ Chairman of the Board Bob Nutting has focused on improving the roster in recent seasons. In 2025, calls among fans to either spend or sell the club reached a feverous pitch. With the exception of right-hand starter Paul Skenes, winner of the 2025 National League Cy Young Award, everyone, at every position, could consider themselves on notice concerning their roster status.
Last season’s club finished dead last in scoring, with the fewest runs (583) among all MLB teams. The .231 batting average achieved by the Pirates has them ranked 28th among the 30 clubs.
While Cherington and his associates remain among the three reported clubs in pursuit of the slugging Japanese first baseman Kazuma Okamoto, there remain other quality third basemen known to hit for power to keep in the hunt in making the Pirates a higher scoring club. Eugenio Suárez and Yoan Moncada are likely third basemen candidates to recruit if negotiations for the Yomiuri Giants’ home run-hitting veteran fall through.
The Los Angeles Angels and San Diego Padres are rumored to be among the three clubs, along with Pittsburgh, that are speaking with Okamoto’s representatives on the West Coast. Alex Bregman, fresh off a successful first year with the Boston Red Sox, is the top third baseman on the free-agent market. His salary demands would probably exceed the Pirates’ payroll projection of $100 million for 2026.
Trading starting pitcher Johan Oviedo earlier this month to the Red Sox in a five-player deal that brought center fielder Jhostynxon Garcia to the Pirates is being hailed a win for Garcia’s new club. Tabbed as an MLB Pipeline Top 100 Prospect, Garcia, 23, appeared in five games with Boston in 2025. Making the jump from Double-A and Triple-A ball last season, before landing in Boston, Garcia should see action with the Pirates in 2026.
Ryan O‘Hearn chose to sign a two-year, $29 million deal with the Pirates earlier this month. The first baseman-outfielder’s agreement is the first free-agent multi-year deal given by Pittsburgh since 2016. O’Hearn, the Baltimore Orioles’ representative at the 2025 MLB All-Star Game, was traded to the San Diego Padres last July. The 17 home runs and 63 RBIs smacked by O'Hearn, 32, in 2025 represent just the offensive upgrade Cherington has been searching for.
The three-team trade involving the Pirates, Houston Astros, and Tampa Bay Rays that went down on Dec. 19 further added potential runs to Pittsburgh manager Don Kelly’s lineup, with the addition of second baseman Brandon Lowe, outfielder Jake Mangum, and left-handed reliever Mason Montgomery. Lowe is coming off his eighth MLB season, all with Tampa Bay. The 31 home runs and 83 RBIs he generated are what Cherington and Kelly are hopeful will be duplicated with the Pirates. Last season’s Pirates’ home run leader Oneil Cruz clubbed 20 round-trippers. Right fielder Bryan Reynolds’ 73 RBIs, tops for a Pirate in 2025, trailed Lowe’s production with the Rays.
Montgomery, who in 2025 experienced his first full MLB schedule, tossed impressive numbers in relief. His 61 strikeouts in 46 innings made the lefty an attractive trade chip, when Pittsburgh acquired a pair of bats with the Rays. After experiencing his rookie campaign in South Florida, Montgomery expresses excitement to spend his sophomore season in Western Pennsylvania.
“I’m very grateful even to be considered for a new role,” Montgomery told The Epoch Times on Tuesday of his joining the Pirates’ relief corps.
Although Montgomery says he hasn’t yet met any of his new teammates, having Lowe and Mangum joining him promises to make his acclimation to the Pirates a bit more comforting. His appearance in 57 games last season has given Montgomery a confidence boast in advance of arriving in February to spring training camp in Bradenton, Florida.
“Going from being a starter to a reliever has worked out well,” Montgomery says. “At first, I was indifferent to making the switch. But, it’s been the best thing to happen to me in my career so far.”
After never having played a game at Pittsburgh’s PNC Park in his young career, Montgomery says he hears nothing but “a lot of good things” about his new home field and playing before the hometown crowds.
“I’m open to trying new things in 2026. As a reliever, I have to be ready to come into a game at anytime. In my mind, I'll be ready to throw 23–30 pitchers each outing.”
The madness of producing a losing record, season after season, is no longer seen as acceptable for the Pirates. Management expects more from the players. Fans demand positive changes to the roster in 2026. Finishing last in the National League Central Division for a third year in a row is unacceptable for anyone associated with the club.
On Cherington’s watch, it’s out with the old and in with a new and improved product put out by the Pirates.
