The Pittsburgh Pirates are not a serious professional sports franchise. Unlike other small-market Major League Baseball teams that struggle to spend money, the Pirates have a dedicated fan base willing to show up for games, ample media coverage, and a franchise pitcher taking the hill every five days.
Yet, led by one of the worst owners in sports, the terminally obtuse and profiteering Bob Nutting, who has drawn official complaints from the players’ association and investigations into his distribution of revenue sharing funds, the Pirates are going to Pirate. And on Thursday’s MLB trade deadline, they set new standards of ineptitude.
Instead of improving his team, general manager Ben Cherington flexed the organization’s decades-long incompetence with one of the most inexplicable trade deadline performances in recent memory.
Cherington has been on the job since 2019, and the team has posted a losing record in each. This year will be no different. The trades have gotten worse … and worse. Colleague Alan Saunders, who is a straight-laced and professional as they come, swung a big stick Thursday evening.
Pitching is a great strength of the team. Paul Skenes is dominating opponents with a 1.83 ERA, but has a mere 6-8 record. That’s only the tip of the iceberg on how sad the Pirates’ hitters have been.
Despite one of the better pitching staffs in MLB, which ranks seventh in ERA (3.68), second in shutouts (13), and fifth in allowed batting average (.232), the Pirates used none of their pitching depth to help the team.
They acquired no players who will provide a tangible impact on the 2026 season.
Instead, Cherington traded away one of his emerging starting pitchers, Bailey Falter, who sported a 7-5 record on a losing team and a healthy 3.72 ERA for practically nothing. Falter brought back a 28-year-old reliever with five games of MLB experience and an undrafted single-A prospect.
The reasoning was that the el-cheapo Pirates didn’t want to pay Falter this winter. According to Cherington, Falter was a “non-tender candidate” this fall.
A guy making $2.2 million is a non-tender candidate?
That might wash if the Pirates had not already cleared tens of millions of dollars in 2026 salary. Not counting Falter’s puny salary, the Pirates cleared about $16 million in payroll by trading away defensive specialist third-baseman Ke’Bryan Hayes, premier closer David Bednar, and rental reliever Caleb Ferguson.
For the Pirates’ booty, they acquired two players in Low-A, three players in High-A, one Single-A player, a Triple-A player, and one MLB reliever who has pitched only five innings.
Oh those Pirates. So close to being competitive, but so futile.
The Pirates are last in baseball with 72 home runs, which is a staggering 20 fewer than 29th place, and are 28th in batting average.
So, the Pirates traded some of their veteran players on expiring contracts for young prospects who are close to major league-ready, right?
Nope. Actually, they will clear another $16 million this winter as veterans on expiring contracts likely run from Pittsburgh as fast as they possibly can.
Andrew Heaney, Tommy Pham, and Isiah Kiner-Falefa came from winning teams. While Cherington gave away a seemingly valuable starting pitcher, those three were not traded and will walk for nothing.
Huh?
And this is why the Pirates are perennially a laughing stock. They don’t just make terrible decisions, they make obviously terrible, self-destructive decisions with a near internal immunity to the consequences.
The plan might take shape for other teams with a track record of success. The Pirates cleared salary to rebuild around their star pitchers. Except they have annually not been able to attract free agents, and no one–absolutely no one–trusts Nutting to release the funds to do so.
The Pirates were already 27th in MLB payroll.
The Pirates have had three winning seasons in the last 33 years, one wild card series win, and otherwise lots and lots of penny-pinching and losing. Sadly for the team that plays in one of the most beautiful stadiums in all of sports, a trade deadline that could have propelled them toward competitiveness was yet another loss and another embarrassment.
At this point, you can start the clock on the Skenes trade. And this is why the Pittsburgh Pirates suck.
