Let’s say you’re Ben Cherington. Let’s say you’ve won a World Series as a general manager of a Major League Baseball team (Boston, 2013), and you’re still young (45 years old).

Let’s say you’re ready to get back to running a ballclub. You’ve spent the last three years as VP of Baseball Operations at Toronto, but the competitive juices are flowing and you want to run your own show. You’ve already turned down opportunities to interview for the GM job with the New York Mets (huge market, excellent starting pitching in place) and the San Francisco Giants (always itching to win).

But you wait. The time isn’t right. You’ve got the pedigree, you’ve got a plan, and you’ve earned the right to pick and choose. You’re ready for the perfect opportunity.

And … it’s the Pittsburgh Pirates.

WHAT?!?!?

Sure. And Brad Pitt is gonna start dating Rosie O’Donnell. Roger Goodell is bringing Super Bowl LV to Moundsville. Maybe Led Zeppelin will reunite for a rap tour. Actually, all of that may come true if Brad, Roger and Robert Plant hang around Bob Nutting long enough. The dude can sell.

“Pittsburgh is the ideal opportunity for me, and the only one I was interested in exploring,” Cherington told MLB.com on Monday. “The four pillars that will drive our success are elite talent identification, acquisition, development and deployment. My entire career has been spent focusing on developing great systems to be elite in these four critical areas, which will fuel our future success in Pittsburgh.”

Cherington withdrew his name from consideration for the GM role in New York and San Fran last year because neither club was ready to tear it down and start from scratch. Apparently, the Pirates are ready to do just that, even though they aren’t revealing plans just yet. The Cherington hire, however, is proof positive. Chances are, they don’t want to announce a full rebuild until they hire a manager. Managers for teardowns/rebuilds have a short shelf life.

A photo of Ben Cherington in a jacket and tie.
He was the general manager in Boston between 2011-2015, and he built a World Series champion in 2013.

OK, so let’s take this to the next level. Let’s say you hang onto young stars like Bryan Reynolds and Kevin Newman. Are you then dealing your few assets to restock a barren farm system? Starling Marte is 31 years old but has two more years on an affordable contract. He’s the team’s best player and could fetch something akin to the Andrew McCutchen trade. Slugging sensation Josh Bell is 27 but coming into those expensive arbitration years. Those two are the hubs of the lineup, but most attractive to other clubs, too.

Cherington knows how to build a farm system. The real test comes when the Pirates start to climb, like the memorable 2013-15 seasons when Nutting saw the turnstiles clicking at PNC ,the excitement in the city, and the cash registers humming. He refused to pull the trigger to spend that extra $omething to $end the team over the top.

In an interview with DKPittsburghSports.com:

“Those are areas where, as you know, we’ve fallen short,” said Nutting, his eyes blankly conjuring up visions of what should have been. “We have some real success in 2013, 2014, 2015, and that success may have blinded us a little to some of the deeper challenges we had in the organization.”

I’m pretty sure he’s talking about the deep challenge of the wallet buried in his pants pocket.

Look, Cherington knows his stuff, but the 2013 Boston Red Sox had a payroll of $170 million. The 2019 Pirates had a payroll of $76 million. We all know the score. Ben Cherington is a smart fellow. So, what does he know that we don’t?

“I’m really confident in the resources that are available across the baseball infrastructure,” he told DKPittsburghSports.com, “including the major-league team — based on what I know to be fact, seeing it on paper. And also based on getting to know Bob and Travis (Williams, the new team president), and just getting that deep feeling of how committed they are to this team and this city. So, yes, confident in the level of resources, confident that the support’s there to build a winning team.”

So Cherington has been sold. I’m not Ben Cherington. I tend to believe what I see, rather than what I hear. Bob Nutting became principal owner of the Pittsburgh Pirates in 2007, when the net worth of the club was $274 million. It’s now worth $1.275 BILLION. So, while the Pirates must contend with a small-market revenue base, the money is there. The Milwaukee Brewers, with the smallest market in the MLB and two-third that of Pittsburgh’s, spent $132 on their big-league payroll last year and made the playoffs. The World Series teams, Washington and Houston, were at $181 mil and $177 mil, respectively.

Teams like the Pirates can’t contend every year. That would defy all logic. But with smart stewardship and the willingness to go all-in when that window opens, they can make a run. That fateful season of 2015, for example, saw a small-market World Series champion in the Kansas City Royals. But ya gotta go for it. Shove all chips in.

When pressed on this issue by the Pittsburgh Post-Gazette, Nutting admitted, “I wish there was more money that could be spent.”

Again, one more time: Nutting has increased his worth by ONE BILLION DOLLARS since taking over the Pirates. He’s the kind of guy who would wrench his back picking a nickle up off the ground while delivering bags of cash to his bank. The money is pouring in whether the team wins or not. 

I’ve no doubt that Nutting was embarrassed by his team last season. Anyone would be. Was it enough?

Ben Cherington — and Pittsburgh — will find out soon enough. 

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