Pirates GM Cherington believes deadline moves create options for 2026. In what way is uncertain

Winnipeg Free Press

3 days ago

PITTSBURGH (AP) — The Pittsburgh Pirates arrived at spring training six months ago stressing that it was time to win. They talked about urgency. They talked about internal improvements. They talked about returning to playoff contention for the first time in a decade.
Then the talk stopped, and the games began. And the losses — both on and off the field — mounted. Quickly. And sometimes embarrassingly.
Even the brilliance of superstar ace Paul Skenes and the fresh, no frills approach of manager Don Kelly — promoted after Derek Shelton was fired in May — couldn't stop the last-place club from being sellers at the trade deadline again.
In the span of 24 hours, general manager Ben Cherington sent away former franchise cornerstones Ke'Bryan Hayes and David Bednar in exchange for prospects, most of whom are years away from reaching the majors, if they ever even get there.
It's a pattern that has repeated itself over and over during Cherington's five-plus years on the job. Yet, unlike the early days of his top-to-bottom overhaul — when Cherington tore the major league roster down to the studs while accumulating as many bodies as he could to replenish the club's bereft minor-league system — it comes at a time when expectations both internally and externally are considerably higher.
Yet Cherington believes his approach checked all three boxes required to help Pittsburgh win in 2026, saying the Pirates added a significant group of young players, most notably, catcher/first base prospect Rafael Flores, who has 16 homers between Double-A and Triple-A this season.
The departures
The departure of Hayes at third base, Bednar, a two-time All-Star closer, and left-handed starter Bailey Falter will create opportunities for others down the stretch. Cherington also pointed out the expected exit of veterans currently on one-year deals — infielder Isiah Kiner-Falefa, outfielder Tommy Pham and pitcher Andrew Heaney most notably — will create considerable financial flexibility as Pittsburgh tries to upgrade an offense currently mired near the bottom of the majors in most offensive categories.
'There's always more things like that that you want to do, so I feel really good about the things we did do,' Cherington said. 'I do believe we put ourselves in a stronger position going into August, September and the offseason.'
Yet when pressed on what that fiscal flexibility might look like in practice for a team that regularly begins each season with among the bottom five clubs in terms of payroll, Cherington offered only vague answers.
'We'll be open-minded about free agency,' he said. 'We've pursued legitimate major-league position players in the past here since I've been here and I'm sure we'll do it again. It's never going to be one thing that solves that issue and helps us figure out the offense that leads to a winning team. It's always going to be lots of things and a lot of that has to happen internally.'
Where will help come from?
Therein lies one of Pittsburgh's biggest issues, for all of the success Cherington and his staff have had in identifying and developing young pitchers — there's a very real chance 22-year-old right-hander Bubba Chandler makes his major league debut later this summer — the results when it comes to position players is far more miss than hit.
While 19-year-old shortstop/outfielder Konnor Griffin is currently considered perhaps the top prospect in all of baseball, he is currently in Class A. Termarr Johnson, a first-round pick in 2022, is having a solid but not exactly spectacular year at Double-A.
They will both eventually be everyday players in Pittsburgh, but having that happen by next summer is a stretch.
So it leaves the Pirates in a familiar place: playing out the string knowing exactly what they need to do to be better next year. Pittsburgh was in the same spot last summer, and Cherington's only significant moves during the offseason were to acquire first baseman Spencer Horwitz while taking one-year flyers on Pham and Adam Frazier, who has already been traded to Kansas City.
The results have hardly been surprising. Horwitz has been steady (.252) since missing the first month-plus of the season due to a wrist injury, but the power Pittsburgh hoped would come along remains a work in progress. Pham has emerged from a massive funk to boost his average to .273.
In a way, the Pirates' offense mirrors enigmatic centerfielder Oneil Cruz, who sometimes dazzles with his physical gifts but just as frequently draws attention for his inattentiveness.
A missed opportunity
The inability to score runs has marred a remarkable season by the pitching staff. The Pirates entered Friday's game at Colorado in the top seven in the majors in ERA, led by Skenes and his major-league best 1.83 ERA. The 23-year-old is a Cy Young candidate despite entering the weekend with a 6-8 record.
Just as importantly, Skenes has consistently said and done all the right things since the Pirates took him first overall in the 2023 draft. He brushed off the idea the club should trade him now with his value so high, saying simply 'anybody can play GM.'
Yet his patience might already be wearing thin. Skenes — who will become arbitration eligible after 2026, which will likely mean a hefty raise — told the club's radio network over the weekend that while he thinks Pittsburgh is 'very close' to contending, it must 'consciously and intentionally make moves to get us better' at the deadline.
Thursdays
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Cherington — whose status beyond this season is uncertain as Pittsburgh eyes a sixth straight losing season on his watch — may have finally said the quiet part out loud late Thursday as the Pirates eye another pennant race going on without them. Yes, they'll have money to spend over the winter. Just don't expect a gold rush.
'(Improving) in Pittsburgh is going to be a combination of taking chances, making bets on young players who are unproven,' he said. 'And we've got to continue to do that and be right more often than we're not right on those.'
The clock is ticking. In more ways than one.
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