The Pittsburgh Pirates shook things up at the 2025 MLB trade deadline, making moves that pointed toward a brighter 2026. General Manager Ben Cherington orchestrated six trades, letting go of core players like Ke’Bryan Hayes and local favorite David Bednar.
In return, the Pirates grabbed young talent, opened spots for emerging players, and gave themselves more payroll flexibility. Let’s dig into what this deadline strategy really means for the Pirates’ future.
The Pirates’ Trade Deadline Moves: A Bold Rebuild
This deadline felt like a turning point. The Pirates traded away six players, including three signed through at least 2026.
Names like David Bednar, Ke’Bryan Hayes, Bailey Falter, Adam Frazier, Caleb Ferguson, and Taylor Rogers all left town. For fans, it stung. These guys brought different levels of star power and consistency, but the front office made it clear: it’s all about the long game now.
Breaking Down the High-Profile Trades
The biggest shock came when David Bednar, a Pittsburgh native and crowd favorite, went to the New York Yankees. The Pirates got three prospects in return: outfielder Rafael Flores, pitcher Edgleen Perez, and infielder Brian Sanchez.
Cherington admitted higher-ranked prospects were possible, but the Pirates chased fit over hype. You can see the calculated risk here—this front office really wants a sustainable, competitive roster, not just flashy names.
Minutes before the buzzer, lefty Bailey Falter was shipped to the Kansas City Royals. In exchange, the Pirates picked up first baseman Callan Moss and reliever Evan Sisk.
These trades aren’t just about a quick fix. They show a real focus on building talent throughout the roster, even if it means some short-term pain.
A Vision for 2026: Setting the Stage for Success
After the deadline, Ben Cherington pulled back the curtain a bit on the Pirates’ plan. He pointed to three main goals:
- Younger Talent Acquisition: By adding prospects, the Pirates aimed to boost their farm system and set up for long-term competitiveness.
- Opportunities for Emerging Stars: The moves opened doors for up-and-coming players in the organization to step up at the MLB level.
- Payroll Flexibility: By moving out some multi-year contracts, the Pirates have more financial wiggle room for future free agency.
It’s a forward-thinking approach. With more flexibility, the Pirates can develop their own talent and look outside for upgrades when the offseason rolls around.
All Eyes on Prospects and Player Development
The farm system’s already looking promising. Several pitching prospects are lined up for their shot at the majors.
Bubba Chandler stands out—he’s considered one of baseball’s top prospects. With roster spots now open, these young guys have a clearer path to the big leagues.
The rest of the 2025 season? It’s really about player development, not chasing wins. Cherington stressed how important it is to nurture the new talent and keep an eye on the offseason for more chances to shape the roster.
What’s Next for the Pirates in the Offseason?
The trade deadline laid out the Pirates’ intentions, but they’re not done yet. Cherington hinted at more moves coming this offseason.
Will they chase free agents, make more trades, or double down on development? Hard to say right now. But one thing’s clear: the Pirates are thinking long-term and staying flexible for whatever comes next.
The Big Picture: Patience is Key
The trade deadline might feel like a letdown for Pirates fans who want to see instant playoff action. But honestly, these moves point to something bigger—a careful rebuild that isn’t about quick wins.
The front office brought in young, controllable players and opened up some payroll space. They’re clearly betting on long-term success instead of chasing a few short-lived wins.
For fans, waiting isn’t easy. Still, it’s probably the only way to see if this whole strategy actually works out.
Looking ahead, the 2025 season is all about building the base. Maybe prospects get their first shot at the majors, or maybe the team just makes sure the foundation’s ready for a stronger offseason.
Honestly, it’s tough not to wonder—will Cherington’s plan really work by 2026?
Here is the source article for this story: After multiple trades, Pirates GM Ben Cherington offers insight into deadline strategy
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