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Ben Cherington then and now

MLB: Arizona Diamondbacks at Pittsburgh Pirates
I’ve been here before, yinz.
Charles LeClaire-USA TODAY Sports

Let me tell you a story.

Once upon a time, there was a terrible baseball team. Sure, they’d had success in the past, even won a couple of World Series, but at the point in time of which I’m speaking, they were terrible. Their fans were yelling for the heads of everyone involved, mainly the owner, who they decried as being cheap and more interested in other things, primarily the English Premier League team he’d just bought.

The general manager, a young man widely considered to be somewhat of a genius since he’d brought this team a World Series championship for the first time in over a hundred years, was moving on to work his magic elsewhere. Another young man, who’d learned at his hand, took his place. It was rough going. He continually clashed with the team’s president over just about everything. However, he knew talent. He brought talent in by drafts and by careful signings of free agents. Not all of them worked out, but enough did so that he brought in another World Series title. When he decided to leave after another team president came in, his legacy continued. To this day, players involved in his deals form the nucleus of the team, which won another World Series three years after he left and is currently in contention to get to yet another.

Although I’ve spent a good chunk of my life hating the Red Sox, I can’t deny what Ben Cherington did with them. This is why I was happy when the Pirates brought him on as GM in 2019. For me, there was no more tangible sign that Bob Nutting wanted to right the Pirate Ship than hiring Cherington, who would love to duplicate the feat of his mentor, Theo Epstein, and win it all with another team. At least the Bucs have won a World Series within the last fifty years, which is more than the Cubs could say when Epstein took over.

Hold on, I need to get some cheese for the whine that’s coming up.

But Nutting is CHEEEEAAAP!! He never wants to speeend! All he wants to do is tank for draft picks! The Pirates will never win anything as long as he owns them!

Here, I brought some Ritz crackers too. Enjoy your snack.

Sometimes I think I spend too much time repeating myself here, but if you guys are going to come up with the same old whines, I’m going to keep putting up the same rebuttals.

First and foremost: the idea that a modern professional sports team will deliberately lose games for what amounts to a lottery ticket is ludicrous, bordering on insane. Secondly, think again if you believe Nutting is the only MLB owner who doesn’t like to spend money. Thirdly, the man responsible for your biggest complaints, namely the Andrew McCutcheon and Chris Archer trades, is Neal Huntington, who is long gone. Yes, the Pirates were cursed with not one but two horrific GMs in a row—let us never forget the dumpster fire that was Dave Littlefield.

Ben Cherington is not following in their footsteps. Yes, he had more money to play with on the Red Sox. Yes, as the BD Commentariat pointed out a few times, some of his free agency picks in Boston weren’t great (hello, Pablo Sandoval). However, his most significant move during his tenure with the Red Sox came in 2012 when he got the Dodgers to take on the bloated contracts of Josh Beckett, Carl Crawford, and Adrian Gonzalez in exchange for the MLB equivalent of next to nothing. In one fell swoop, he freed up over a quarter of a billion dollars, which he then used to pick up free agents like Shane Victorino, Mike Napoli, and Koji Uehara, who in turn contributed big time to the Red Sox’s World Series win the following year. It was only the second time in MLB history that a team that finished last in its division one year won it all the next year; the first to do it was the 1991 Twins.

Red Sox Nation’s major complaint about Cherington was that he wasn’t willing to pay future free agents to keep them in Boston (sound familiar?). For example, many tears ensued when he let outfielder Jacoby Ellsbury walk in 2013 to OMG NO THE YANKEES. That the deal is considered one of the worst contracts in Yankees history—and that’s saying something—speaks to Cherington’s savvy. Ellsbury’s primary gift was his speed, but he was 30 years old and starting to develop a troubling injury history. As it turned out, that history came into play quite a bit during his time on the Yankees and ended his playing days before his contract ran out.

No move that Cherington has made as Bucs GM has surprised me so far. He’s doing exactly what he did in Boston, although the dollar amounts involved are much smaller. The latter part of the 2021 season was an audition for the higher-echelon minor leaguers, whether drafted by the Pirates and obtained through Cherington’s wheeling and dealing. As far as paying players to stay, the first test will be Bryan Reynolds, eligible for arbitration next year. He’ll be 27 and in the prime of his career. He becomes a free agent in 2026 when he’ll be 31. Let’s face it, the Pirates are already getting high draft picks, so it’s not like Cherington will do what he did with former Red Sox closer Jonathan Papelbon and trade Reynolds for two choice draft spots. If Cherington wants to build the Pirates into a longtime contender, Reynolds will be the lynchpin to keep the Bucs train together. I’m not saying that Cherington would never trade Reynolds, as these days no one is really safe from that, but it’s going to take more than a couple of top prospects to tempt him to do so.

In other words, 2022 is also Ben Cherington’s test year. He’s got the people he wants coaching in place, he’s gotten rid of dead weight in players, and he’s helping to grow the next generation, whether drafted or picked by him or others. But, unlike Boston, where both John Henry and then-team president Larry Lucchino tangled with him, both Nutting and Travis Williams seem to be taking a hands-off approach, letting Cherington run things as he sees fit.

After all, a lot of the seeds he sowed with the Red Sox grew into well-performing fruit.