Last night was the same movie fans in Pittsburgh have seen time and time again: a rollercoaster, back-and-forth game that ultimately ended in heart break, the same way so many others have.

The pitching was rocky; starter Jared Jones had another subpar start, giving up four runs (three earned) in less than five innings of work. He has yet to make it past the five inning mark since returning to play this season. Evan Sisk, the first reliever to follow Jones, was also eventually charged with two earned runs. But hey, when your upper-tier offense scores seven runs, you have a strong chance of winning any given game.

And when the ninth inning rolled around, the Pirates needed one more arm to get them across the finish line.

A one-run game in the top of the ninth, against a divisional rival, in front of a Saturday night crowd, with the chance to remain above .500 and keep pace in the wild card round. That’s the exact scenario you have in mind for your closer, the reliever you trust more than anyone else in that bullpen.

For this year’s Pirates, that title first belonged to Dennis Santana. But after a fall from grace and an extreme rough patch he’s still working his way out of, the job fell to free-agent signing Gregory Soto.

Soto, who in 33.1 innings prior to last night carried a 3.24 ERA, 0.990 WHIP, and 3.00 strikeout-to-walk ratio, was the man called upon. He was one strike away from getting out of it, but almost Pirate and definite Red Eugenio Suárez smacked a three-run homer to flip the game for Cincinnati.

Look, baseball can be a cruel game. Hundreds of pitches are thrown each and every game, and you won’t ever know what toss will mean the most until it’s too late. No closer is going to convert every save situation they enter, that’s just the nature of the sport.

When you have a team that leads has blown 17 saves (half of their 34 opportunities), has lost 11 games when scoring six or more runs, and three games after leading through eight innings, it’s no longer a one-off to be ignored. When not a single name coming out of that pen can be trusted, it’s no longer something the Pirates can endure.

Walking away from that ballgame, I only had one thought: the Pirates have no choice but to buy at the trade deadline.

I read Noah Hiles’ column the other day in the Post-Gazette. He argues that the Pirates, other than the small tinker here and there, aren’t worthy of being buyers at the trade deadline. He makes a compelling argument, one that only feels stronger after the Pirates blew another game the way they did on Saturday.

But I’m going to go in a different direction.

Look, Ben Cherington’s time as general manager here has been nothing short of an abysmal failure. The Brandon Lowe trade, the Ryan O’Hearn signing, and the Konnor Griffin selection in the draft are all great moves. Give him credit for those.

But at no point during his time here have his Pirates finished within ten games of a winning season. His career record in control of the club is 406-547. This is not explicitly an anti-Cherington sentiment, or a piece calling for his immediate firing. Any executive who sported such figures would be considered a failure at the job. That’s just the truth.

What is also the truth is that this year, the 2026 team, represents the best chance yet for both Cherington and the Pirates to snap this wretched streak that has haunted them for years.

The aforementioned moves for Lowe, O’Hearn, and Griffin have contributed majorly to one of the better offenses in baseball, a unit averaging over five runs a game. But as has been the case during Cherington’s entire time here: nothing is ever complete on this roster.

When the pitching is working, the batting isn’t. When the team can hit, they can’t get an out.

Not a single person in baseball fears this bullpen. In fact, they crave the opportunity to face it. When you play against the Pirates, the goal is to get to the bullpen as quickly as possible. The sooner Don Kelly has to make his first call, the better an opponent’s chances are of winning.

And when you have a rotation featuring several arms who struggle (whether via poor performance or pitch counting) to go deep into games, it only makes Kelly and Pittsburgh’s job all the much harder.

There’s a growing frustration towards the players themselves for their faults on the field. I get it, at a certain point the players have to execute. But there’s only so many times they can show you that they simply can’t before the problem becomes bigger than them. I think we’ve been there for a while now.

Earlier this month, I wrote about this same issue. Back then, I said the current state of the bullpen represents the difference between acting like a good general manager, and actually being one.

Cherington’s body of work, at large, suggests he shouldn’t have a job here anymore. Another playoff-less, losing season (which the Pirates are now on pace for) should assuredly do it for him here. If he wants to get anything worth remembering done here, this is his best shot.

And if Pirates want anything worth remembering from their favorite team, this might be the last chance they have for a while.

With every passing day, the possibility grows more and more that we won’t see a lot, if any, baseball played in 2027. Ahead of the pending expiration of their collective bargaining agreement at the end of this season, the MLB and MLBPA are clashing on a number of issues. Chief among them, of course, is the issue of a salary cap. The union is still vehemently against it; Paul Skenes himself has made staggering comments against the idea of a cap.

By the time 2028 rolls around, who knows what the Pirates, or baseball, will look like?

Cherington is the biggest reason why this is the team’s best year. That’s both a compliment and an insult to his work. But I just do not believe the Pirates can afford another year of non-competitive, non-committal baseball. Cherington’s been doing this for seven years now.

If the 100-loss seasons, the years of abject misery, the frustrating mid and late-season collapses, and the heartbreaking loss after heartbreaking loss are ever going to be worth it, it has to come here and now. Go out and make legitimate, impactful moves to address the weakest link of this team.