VOTE: Does Ben Cherington get fired if the Bucs miss the MLB Playoffs?
PITTSBURGH - The calendar says August 11, but the Pittsburgh Pirates are already playing October baseball. Not the crisp, cool kind with packed stands and white-knuckle tension. No, this is the suffocating kind where every late-inning bullpen move feels like a referendum, and every blown lead echoes all the way up to the GM’s office.
We’re past the trade deadline. The roster is set. The excuses are spent. And the question burning through the Steel City isn’t just whether this young core can finally punch a postseason ticket - it’s whether General Manager Ben Cherington’s job security is now tied directly to October baseball.
Let’s be real: the "rebuild" label is dead. Cherington has spent money, unleashed top prospects, and flipped the organizational narrative from "trust the process" to "watch the product." But the National League Central is not a gauntlet. It’s a winnable division with a wide-open Wild Card chase. If the bullpen coughs up another late lead against a division rival, or the bats go catatonic in a four-game set that matters, the leash gets shorter by the day.
This is no longer about prospect rankings. This is about wins. And right now, the evidence is mixed - with the clock ticking louder than the train in left field.
The Deadline Signals: Buying or Barely Hanging On?
The trade deadline told us everything we need to know. The Pirates didn’t sell off controllable assets. They didn’t wave the white flag. Instead, they held their core and added a rental arm - a clear, unmistakable message: "We think we can do damage."
But here’s the catch: when you don’t sell, you’re betting on winning. You’re telling ownership, the clubhouse, and the fanbase that this group is good enough. If the team fades in September with a whimper, that bet doesn’t look like vision - it looks like stubbornness. And stubborn GMs with empty Octobers don’t last long in Pittsburgh.
| Opponent Tier | Games Left | Home/Away | Win Impact |
|---|---|---|---|
| Division rivals (CIN, MIL, CHC) | 18 | 10 Home / 8 Away | High - head-to-head tiebreakers |
| Contenders (LAD, PHI, ARI) | 9 | 5 Home / 4 Away | Medium - must steal 2 of 3 |
| Bottom feeders (MIA, WSH, COL) | 12 | 6 Home / 6 Away | Critical - no excuses |
That’s 39 games left. Roughly 26 of them are against teams with playoff aspirations or division grudge matches. There is no soft landing. There’s only the grind - and the verdict that comes with it.
The Case for Keeping Cherington: Context and Contracts
Nobody’s denying the roster is more talented than it was three years ago. Cherington inherited a bare cupboard, and he’s turned it into a pitching pipeline that any organization would envy. The development of arms in this system isn’t a fluke - it’s a factory. And the recent wave of young bats finally arriving in Pittsburgh isn’t accidental either. There’s a blueprint, and you can see it on the field most nights.
📊 [Top-10 rotation in baseball by team ERA this season] - The pitching staff is legitimately elite, a direct result of Cherington’s investment in development infrastructure.
But there’s a bigger factor at play here: contract security. Cherington reportedly has more than just this season on his deal. Owners don’t often eat that money unless the collapse is spectacular - and missing the playoffs by a game or two does not qualify as spectacular. Not when you’ve successfully restocked a barren farm system and built a top-10 rotation.
Plus, let’s ask the uncomfortable question: who replaces him? The list of executives who can navigate Pittsburgh’s budget constraints and attract talent is short. You don’t fire the guy who fixed your development pipeline just because the finishing kick is still a work in progress. Change for change’s sake is how you end up in another five-year rebuild - and this fanbase has had enough of those.
