Ben Cherington hits Pirates milestone nobody wanted (and then made it worse)

Friday should have been a sobering milestone for Ben Cherington. Instead, two days later, the Pittsburgh Pirates general manager was talking about a September hot streak.

Game No. 1,000 of the Cherington era came and went at Dodger Stadium with the Pirates exactly where they have spent almost his entire tenure: below .500, outside the playoff picture and trying to convince everyone that something better might still be right around the corner.

Entering Sunday 7.5 games out of a playoff spot, Cherington acknowledged the obvious difficulty of Pittsburgh's position but refused to close the door on October. With Oneil Cruz and Spencer Horwitz healthy, Konnor Griffin potentially returning soon and Ryan O'Hearn hopefully following later, Cherington believes the Pirates could field their best roster of the season in September.

“We haven’t had a hot streak all year that most teams have,” Cherington said on his weekly radio show Sunday on 93.7 The Fan. “I think it’s possible we have the best team we’ve had all year. It’s possible, and I think it’s true, we haven’t had a real hot streak. No matter the odds or the standings, I see the potential for a hot streak in September.”

Seriously? After 1,000 games, we're still talking about potential?

There might be nothing more fitting about Cherington's Pirates tenure than reaching a four-digit games milestone and immediately pointing toward a winning streak that hasn't happened as evidence that this team could still turn things around.

The Pirates' longest winning streak this season is five games. It happened from the final day of March into early April.

Maybe they do get hot in September. Baseball is weird. Bad teams win eight straight sometimes, and good teams lose eight straight sometimes. But that's precisely why invoking a hypothetical hot streak misses the larger point.

Cherington shouldn't be evaluated on what the Pirates might do over a random 10-game stretch in September. He should be evaluated on the previous 1,000 games — and that evaluation is ugly.

Pirates have 1,000 games of evidence that Ben Cherington’s ‘hot streak’ talk can’t erase

The high-water mark of the Cherington era remains 76 wins. Pittsburgh has not produced a winning season under his leadership. The rebuilding years were supposed to eventually give way to contention, and entering Year 7, the Pirates finally stopped hiding from expectations. This was supposed to be a playoff team.

Instead, they're once again staring at September from the outside.

There were legitimate improvements this year. Cherington built one of baseball's better offenses, and after inexplicably allowing the bullpen to remain a glaring weakness for most of the season, he aggressively repaired it at the trade deadline.

Those things deserve acknowledgment, but they also aren't enough. This is Year 7, not Year 2.

Cherington carried a broken bullpen for four months before fixing it. He devoted a roster spot to Marcell Ozuna for four months despite almost no production and the obvious baggage that came with the move. The defense has been an enormous problem. A starting rotation that was supposed to be the foundation of the roster showed cracks, yet Pittsburgh didn't meaningfully supplement it. And even after being aggressive at the deadline, the Pirates still didn't add the right-handed bat their lineup clearly could have used.

In the early stages of a rebuild, those are lessons. Seven years into one, they're evidence.

Every general manager has injuries and players who unexpectedly regress. Every contender has somebody go off the rails. Cherington can point to Cruz missing significant time, Griffin getting hurt, O'Hearn landing on the IL and any number of other setbacks. None of those things absolve the person who constructed the roster.

Ben Cherington’s 1,000th Pirates game should be a wake-up call, not reason to preach patience

The problem with Cherington's comments isn't that he's required to publicly surrender the season. Obviously, he isn't going to go on the team's flagship radio station and announce that everyone should stop caring about the final month. But the rhetoric still sounds so painfully familiar.

Wait until everyone is healthy. Wait until the prospects arrive. Wait until this group gets a chance together. Maybe they're better than the record shows. Maybe a hot streak is coming.

Pirates fans have spent seven years waiting for the “maybe” to become something tangible. At some point, finishing what you start should apply to the front office, too.

Cherington also pushed back on the idea that Pittsburgh should automatically begin shutting players down if the postseason becomes effectively unreachable.

“The MLB season is a precious thing and we all have a job to do, including the players,” he said. “If there is a risk not worth taking, we will make adjustments. If not, there is value in that you finish what you start.”

That's a perfectly reasonable philosophy in isolation, but it also creates an unavoidable question for ownership. What happens when seven years of evidence says the general manager has finished what he started?

Cherington is reportedly under contract through 2027, and it's easy to imagine the Pirates pointing toward this season's injuries, the improved offense, the deadline additions and the possibility of a healthier roster next year as reasons to give him one more chance. They shouldn't. One thousand games is more than enough of a sample.

The Pirates don't need another September hot streak to determine whether the Cherington era has worked. They have seven years of evidence, and no hypothetical winning streak over the next five weeks should erase it.

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