Ben Cherington just completed his sixth trade deadline as general manager of the Pittsburgh Pirates with another flurry of moves. In July, he completed six trades, giving up six players to five different teams, receiving 10 in return. We’ll give each trade a letter grade before grading Cherington’s performance overall. For fun, we’ll also report who “won” each trade using the value system per Baseball Trade Values.
Grading the Pirates and Ben Cherington at the Trade Deadline
Last Sunday, during a gathering with the local media, Cherington said of the trade deadline, “I don’t think we can be risk-averse. I don’t think that’s going to work in Pittsburgh. [If] we want to win, we’re going to have to assume risk. . . We need to score more runs to win more games. That’s clear, and that’s a goal going into 2026.” Thus, we’ll evaluate Cherington under this criterion: Did he do enough to improve the Pirates’ ability to score runs in 2026?
First, let’s look at what Cherington didn’t do. He didn’t trade pitcher Mitch Keller, a controllable starter in high demand. Surprisingly, he didn’t trade three players under expiring contracts: pitcher Andrew Heaney, infielder Isiah Kiner-Falefa, and outfielder Tommy Pham. Lastly, he didn’t acquire potentially difference-making prospects like Spencer Jones or Owen Caissie. So, let’s look at what he did.
If Ben Cherington knew he was going to get fired and was trying to make the Pirates pay for it by making horrible moves on purpose at this trade deadline, this is about what it would look like.
— Alan Saunders (@ASaunders_PGH) July 31, 2025
Kansas City, Here He Comes
July 16: Pirates trade infielder/outfielder Adam Frazier to Kansas City Royals for infielder Cam Devanney. Baseball Trade Values score: Pirates 1.1, Royals -0.4.
When second baseman Nick Gonzales went on the injured list on Opening Day, Frazier filled in admirably in his absence, hitting .255/.318/.336 and providing solid infield play. When Gonzales returned, Frazier saw action in the outfield in place of the slumping Pham. But Frazier is playing under a one-year contract. At age 34, he doesn’t fit into the Pirates’ future plans. On the other hand, Devanney, although old for a prospect at 28, hit .272/.366/.565, 18 HR, and 55 RBI at Triple-A Omaha this season. Seemingly, that wasn’t a fluke. He hit 19 home runs at Omaha last year. Whether his bat will translate to the majors is unknown, but he’s a low-risk gamble. Grade: B.
Two Trades in One
July 30: Pirates trade third baseman Ke’Bryan Hayes to Cincinnati Reds for shortstop Sammy Stafura, pitcher Taylor Rogers, and “cash considerations.” Baseball Trade Values Score: Pirates 5.4, Reds -8.9.
July 31: Pirates trade Rogers to Chicago Cubs for outfielder Ivan Brethowr. Baseball Trade Values score: Pirates 1.1, Cubs -0.3.
These two deals must be evaluated as one, as the Pirates clearly had no intention of hanging onto Rogers. Rumors circulated that the Pirates would trade Hayes, simply to get his contract off the books. Although a Gold Glove winner in 2023 and one of the best defenders at any position, the offensive production wasn’t there to justify the $30 million he’s owed over the next four years. Recurring back problems and a 49.3 percent ground ball rate for his career hurt his offensive production, with no apparent end in sight. Over 2024 and 2025, Hayes hit .234/.281/.290, 6 HR, and 61 RBI. Playing a power position, he’s hit 39 home runs in six seasons. It’s a trade that’s more about what the Pirates gave up than what they got. Besides, Rogers can say he never gave up a run while with the Pirates. Grade: A.
Great Baseball Name
July 30: Pirates trade pitcher Caleb Ferguson to Seattle Mariners for pitcher Jeter Martinez. Baseball Trade Values score: Pirates 2.8, Mariners 1.1
As one of the Pirates players under an expiring contract, Ferguson was sure to be traded at the deadline. He was effective in high-leverage relief situations, with a 3.74 ERA, distorted by two bad outings, and a 1.085 WHIP. Batters made hard contact against him just 25.4 percent of the time. Meanwhile, the Pirates get a big, 19-year-old with a cool name who was Seattle’s No. 13 prospect. He’s not what the Pirates need right now, however, but probably as well as one could expect for a rental. Grade: C.
Now It Gets Weird
July 31: Pirates trade pitcher David Bednar to New York Yankees for catchers Rafael Flores and Edgleen Perez and outfielder Brian Sanchez. Baseball Trade Values Score: Pirates 12.7, Yankees 7.4.
Today the #Yankees reportedly acquired RHP David Bednar ($7.4M surplus trade value) from the #Pirates in exchange for Cs Rafael Flores ($7.3M) and Edgleen Perez ($4.3M) and OF Brian Sanchez ($1.1M) ($12.7M total).
The deal is rejected by our model as an overpay by New York.
— Baseball Trade Values (@BaseballValues) July 31, 2025
In Bednar, a two-time All-Star under team control through 2026, Cherington had a valuable trade chip. Furthermore, it was thought that if Cherington were to trade such a valuable piece, he’d get one or two major league-ready bats in return. Instead, he got the Tijuana Brass. Of the trio surrendered by New York, only Flores is projected to arrive in the majors next season. He has a good eye at the plate, raw power, and high exit velocities. However, while he may be ready to hit in the majors in 2026, his defense needs work, and that may keep him in the minors longer than expected. Perez and Sanchez are in High-A. If the goal was to get better in 2026, as Cherington said it was, the Pirates would have been better off just to keep Bednar. It’s a bitter end to Bednar’s Pirates tenure. Grade: F.
Cherington Falters Again
July 31: Pirates trade pitcher Bailey Falter to Royals for pitcher Evan Sisk and first baseman Callan Moss. Baseball Trade Values score: Royals 3.6, Pirates 0.8.
What did this trade accomplish other than a salary dump, and a relatively inexpensive salary at that? Falter was an effective starter having his best season, posting a 7-5 record, 3.73 ERA, and 1.182 WHIP. He’s arbitration-eligible next season, and although surely due a raise from this season’s $2.22 million, he wouldn’t have bankrupted the team. In return, they got two unranked prospects. Sisk is a 28-year-old left-handed pitcher. Falter is also a 28-year-old left-hander. Moss is a lottery ticket. Good grief. Grade: F.
The Last Word
According to Baseball Trade Values, the Pirates largely won this trade deadline. Perhaps time will tell that they did, should the many low-level prospects they received pan out. But no Pirates fan will care about that, nor should they. Six trades yielded only two players, Flores and Devanney, who might be in the majors next season. Cherington fell well short of the goal of improving the Pirates’ offense in 2026. There’s still time to improve the 2026 Pirates by putting the cost savings from Hayes, Bednar, and Falter into major league hitters in the coming offseason. However, this looks like the start of yet another five-year plan. If it walks like a duck and quacks like a duck. . . Overall Grade: F.
Main Photo Credit: Charles LeClaire-USA TODAY Sports
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