Thursday was a defining moment for general manager Ben Cherington and the Pittsburgh Pirates. Amidst another disappointing season and several attractive trade assets to work with, Cherington had the pressure on him to try and turn around the ever-worsening negative reputation he has garnered in this town.

Instead, his work at the MLB trade deadline only solidified the disgust that Pirates fans have for this front office.

I’ll be honest: if fans were asked to conjure up a nightmare scenario of how the 2025 deadline would go, I’m not sure they could have imagined it going quite this bad.

Cherington’s work made winning in 2026 infinitely more difficult, and in a market that saw some pretty seller-friendly trades, one could argue the Pirates lost every one that they made. It was demoralizing in a season that has been full of heartbreak, despair, and frustrarion.

In a normal world, who the Pirates didn’t trade would be seen alone as a disaster. Lefty starter Andrew Heaney, outfielder Tommy Pham, and shortstop Isiah Kiner-Falefa are all still on the team, despite all being on expiring contracts and are incredibly unlikely to re-sign in the offseason.

However, that pales in comparison to what the front office actually did do at the deadline.

Not only did the Pirates deal several important players off their major league roster, they failed to replace them with anyone who is major league ready. None of the players acquired by the club during the deadline craze will report to Pittsburgh for now.

The closest major leaguer they received in any deal was Evan Sisk, a left-handed reliever who the Pirates acquired as part of the surprise Bailey Falter deal. Sisk was referred to as a prospect, but at 28 years old, Sisk is now a project, one that took until this season to make it to the major leagues.

He tossed 5.1 innings in the bigs with Kansas City over two separate stints, with his most recent MLB game coming back on May 27th. Since he returned to Triple-A Ohama after that appearance, Sisk has gotten lit up. In 16.2 innings, Sisk has posted a 5.94 ERA and 1.980 WHIP. Triple-A opponents have slashed .338/.400/.558 against him, with four home runs.

In fairness to Sisk, he has not allowed a run in each 14 of his 19 games since during this run, but he has allowed at least one hit in all but four of those games, and has surrendered multiple hits in six of those games.

It’s a risky move that will try to supplement the loss of Bednar in the bullpen.

In the position player department, the closest to making an impact in Pittsburgh is catching prospect Rafael Flores, who headlined the payment the New York Yankees made for Pirate closer David Bednar.

Flores, a 24-year-old catcher, was recently promoted to Triple-A in New York’s system before the deal.

To his credit, Flores has been a productive batter in the farm system so far. He was the Yankees organization’s minor league player of the year last season, a year that saw him slash .279/.379/.495 with 21 home runs and 68 RBI in 124 total games, across High-A Hudson Valley and Double-A Somerset.

This season, he tore up Double-A and led the Eastern League with 39 extra-base hits and 166 total bases at the time of his promotion. He played just ten games in Triple-A Scranton/Wilkes-Barre.

However, his catching work leaves some to be desired. Praised as an excellent pitch framer (a skill that could be greatly diminished as soon as next season), the 6′ 4 righty has a low rate at throwing out runners heading for second.

He caught just 16% of attempted stealers in Somerset and 15% in his limited time in Scranton/Wilkes-Barre. Just for reference, the MLB average this season is 23.7%.

No one else the Pirates received in any of their deals is anywhere close to helping the major league club compete.

Edgleen Pérez and Brian Sanchez, the two other prospects Pittsburgh acquired from New York, are playing in Low-A Tampa.

Sanchez, a 21-year-old outfielder out of Venezuela, was slashing .281/.373/.438 with four home runs, 36 RBI, and 24 stolen bases in 63 games in the Florida State League at the time of the trade.

Pérez, meanwhile, was struggling in the FSL. At 19, the catcher was slashing a measly .209/.368/.236 with 26 RBI in 63 games. Regarded as having “excellent swing decisions,” the Venezuelan has a 17.9% walk rate, but has yet to show any real success actually hitting the ball. Behind the dish, Pérez has thrown out 15% of attempted base thieves.

The same thing goes for Callan Moss, Jeter Martinez, Ivan Brethowr, and Sammy Stafura, the three other prospects the team acquired in separate trades.

Callan Moss, brought in as part of the Falter deal, is a 21-year-old first baseman who has spent most of the season in High-A Quad Cities. There, he slashed .270/.372/.418 with seven homers and 70 RBI. He’s a fine bat to stash farther down your farm system, but it’s a little light for a reliable lefty arm like Falter.

Sammy Stafura was acquired in the Hayes trade, which feels like a lifetime ago at this point. At 20 years old, he slashed .262/.393/.411 with four home runs and 48 RBI in 88 games in Low-A Daytona.

Ivan Brethowr, sent to Pittsburgh from the Chicago Cubs as the Pirates flipped Taylor Rogers, is a High-A outfielder who was slashing .221/.398/.312 in South Bend, with 26 RBI in 83 games. Those numbers aren’t thrilling. Including his start in Low-A Myrtle Beach this year, Brethowr has 28 stolen bases and was plunked an oddly-high 26 times.

Jeter Martinez might be the hardest one to get behind, as of right now. The return for lefty rental Caleb Ferguson was working with a 6.18 ERA, 1.612 WHIP, and 1.58 strikeout-to-walk ratio in Low-A Modesto.

Look, it’s obviously far too early to write off any one of those prospects, as underwhelming as they may be. However, two things are true:

• None of these prospects were ranked particularly high in their respective systems. Flores was the highest, at eighth. Several of them didn’t even place in their respective team’s top 30
• None of them will help the major league team compete in 2026

Yes, clearing out certain players and positions was important, because it was abundantly clear that this particular mix did not work. But nowhere, in any of the trades that Cherington made, did they acquire younger players who could audition for and/or grow into that role on the 2026 team.

Although, if you listen to Cherington, it sounds like he could have acquired a major league player from New York and…didn’t.

At any rate, all this deadline did was create more holes in the roster, with no ready solutions to take over. It was the type of rebuild that we would have seen the Pirates execute back in, say, 2021. It was not the approach any team in year six of a rebuild, and in year two of Paul Skenes, should even be in a position to take.

Paul Skenes doesn’t deserve this. Andrew McCutchen doesn’t deserve this. And most importantly, Pirates fans don’t deserve this.