The 2026 MLB trade deadline is 11 days away, and the Pirates find themselves in a much different spot than they did last year.
Very early on in the 2025 season, it was clear Pittsburgh was not going to be a contender. The Pirates scuffled out of the gate, made a managerial change in early May, and were never close to flirting with a .500 record.
This year, the Pirates are poised to add to the big-league roster rather than subtract. But last year’s moves helped shape the 2026 team in more ways than one.
Let’s revisit the deals general manager Ben Cherington made leading up to last year’s deadline.
Pirates Acquired INF Cam Devanney From Royals for INF Adam Frazier
The Pirates made a trade in the middle of July to acquire Devanney from the Royals for the veteran Frazier. This trade didn’t amount to much for either side.
Frazier, now with the Angels, actually performed well in a 56-game sample with the Royals, who missed the playoffs with an 82-80 record. Devanney went 5 for 36 in 14 games for the Pirates and is now playing in Japan.
A forgettable trade all around.
Grade: C
Pirates Acquired RHP Jeter Martinez From Mariners for LHP Caleb Ferguson
The Pirates sent Ferguson, who was on an expiring contract, to the Mariners for Martinez, a young pitching prospect who was just 19 at the time of the trade.
Ferguson went 3-2 with a 3.27 ERA after the trade and helped lead Seattle to the ALCS. Martinez has struggled with Low-A Bradenton this season. He’s 2-5 with a 5.16 ERA in 17 appearances/15 starts but is ranked 25th on MLB Pipeline’s top 30 Pirates prospects list.
Trading a rental reliever made a lot of sense for the Pirates. Such players don’t typically net much in return, but Martinez at least has some upside despite lackluster results. The Mariners were surely happy with their side of things.
Grade: C+
Pirates Acquired LHP Evan Sisk and 1B Callan Moss From Royals for LHP Bailey Falter
At the time, this trade generated a lot of flack (from myself included), but it’s turned out to be quite the pickup by Cherington.
Falter, who was a formidable back-end starter with the Pirates, struggled ever since he arrived in Kansas City, so much so that he’s currently in the minor leagues. Sisk, meanwhile, had been arguably the Pirates’ top reliever this season prior to an arm injury. Moss burst onto the scene with High-A Greensboro after he was acquired. He’s slowed down some with Double-A Altoona, but is still considered an organizational top 30 prospects.
Give credit where it’s due, this was a good trade by Cherington.
Grade: A
Pirates Acquired LHP Taylor Rogers and INF Sammy Stafura From Reds for 3B Ke’Bryan Hayes
Honestly, I have no clue how Cherington convinced the Reds to take on the entire Hayes contract AND get a legitimate prospect back in the deal.
This trade has some layers. Rogers was flipped to the Cubs for outfield prospect Ivan Brethowr, who is in Double-A and not one of Pittsburgh’s top 30 prospects. Rogers was used to offset some of Hayes’ 2025 salary, but the Reds are still on the hook for the $7 million owed to Hayes this year and next, the $8 million owed to Hayes in 2028-29, and a $12 million club option with a hefty $6 million buyout in 2030. Hayes is a world-class defender, but his offense has been abysmal, and lingering back issues continue to be a problem. He’s been hurt most of this year.
Stafura, the prospect the Pirates got back, is No. 10 on the club’s top 30 list and is lighting the world on fire with Greensboro. In 41 games, he’s slashing .317/.380/.652 with 15 homers, 46 RBIs and 15 stolen bases.
Grade: A+
Pirates Acquired C Rafael Flores Jr, C Edgleen Perez and OF Brian Sanchez From Yankees for RHP David Bednar
Like the Falter trade, this one was also head-scratching at the time. Unlike the Falter trade, this one has not panned out, and the Pirates are paying mightily for it.
Pittsburgh’s bullpen has been a huge issue this season and is in need of a reliable closer. Bednar is currently 4-3 with a 2.53 ERA. He’s 18 for 20 in save opportunities this season, whereas the Pirates have blown a whopping 19 of 39 save opportunities.
The return has been lackluster. Flores has mostly served as a depth catcher with Triple-A Indianapolis but has filled in of late for the injured Endy Rodríguez. Perez is having an OK season with Low-A Bradenton. Sanchez has been fine with Greensboro.
But there’s no telling how different the Pirates look this season with Bednar in their bullpen. This is a trade Cherington surely regrets, despite it saving some money that was used in the offseason.
Grade: F
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