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Cherington walks a fine line as GM

As the general manager of the Boston Red Sox from 2011 to 2015, Ben Cherington had one of the largest payrolls in Major League Baseball at his disposal, and enjoyed a great deal of latitude if he made a mistake in a player transaction.

Now in his first season as the general manager of the small-market Pittsburgh Pirates, Cherington, 46, realizes that he must skillfully walk a much tighter rope when attempting to sign free-agent players.

The Pirates, who haven’t made the National League playoffs since 2015, have regularly come under public scrutiny for their preference not to make risky spending moves on high-priced free-agent players.

Cherington, who was the guest speaker at the Blair County Chamber of Commerce’s Breakfast Club luncheon on Wednesday at the Lakemont Park Casino, asserted that the Pirates will spend money to invest in a contending club, but that they must do so judiciously.

“I would say that we want to spend when it’s most valuable to spend,” Cherington said. “When we’re getting closer to being really good, then we need to be in a position to invest in that team to push it over the hump and to add the offense that we need to get for it to be competitive.

“The danger in doing that too soon is (spending) when you’re just not ready as a team to be really good,” said Cherington, who was the director of baseball operations for the Toronto Blue Jays before being hired by the Pirates last November. “Free agency is really hard to get right any way, but there’s a point in time where you absolutely must invest.”

Timing is everything in trades and spending, according to Cherington, who was named Major League Baseball’s Executive of the Year by the Sporting News in 2013, after helping Boston win a World Series.

“(The point where you invest in a team) is a strategic point,” Cherington said. “It should happen right before the team starts to win more games, but not too far before, or you start wasting bullets. It’s up to us to make decisions where we can spend in a way that leads us to becoming a winning team.”

The Pirates have long embraced the philosophy of drafting and developing home-grown talent. It worked admirably in the early to middle part of this past decade, when premium players like outfielder Andrew McCutchen — the National League’s 2013 Most Valuable Player – and outstanding pitcher Gerrit Cole, who was a strong Cy Young Award candidate in 2019 — were in the Pirates’ system.

But when that well goes dry, as it has in the past few years, the wait can be arduous for the team and its fans alike.

That said, the Pirates’ emphasis on finding and developing players of its own has always been a strong suit of Cherington’s, and it spurred him to take on the challenge of attempting to rebuild the Pirates.

“Finding and developing players are the things that I’m the most passionate about,” said Cherington, who pointed out that first-year Pirates manager Derek Shelton shares a similar passion for coaching and managing. “And the bottom line is that in Pittsburgh, we have to be great at those two things. It excites me to be in a place where there is no choice but to be great at those two things.”

The Pirates’ 21-year relationship with their Class AA affiliate, the Altoona Curve, has always been special. Even though the coronavirus pandemic forced the cancelation of all of minor league baseball in the country this year — a situation that Cherington termed “painful” for everybody involved at all levels of the game — Altoona has still provided a very valuable resource for the Pirates by harboring a taxi squad of about 30 players who have trained this summer at Peoples Natural Gas Field.

“What has happened in Altoona this year is just as important as anything that has happened to the Pirates this year,” Cherington said. “The Pirates have had a group of roughly 30 players here in Altoona since July. We’ve seen players get better, we’ve seen players come up to Pittsburgh and perform well, and put themselves in a better position to be part of the team going forward.

“The opportunity to be partnering with the Curve and the people in Altoona has been one of the bigger parts of the year for the Pirates from a baseball development standpoint,” Cherington added.

So is Curve general manager Derek Martin, who was among those on hand Wednesday.

“We could not be happier to have Ben Cherington with us in Altoona today,” Martin said. “It’s great. It shows the commitment and the great relationship thatthe Pirates have with the Curve. I’ve had several discussions over the past several months with Ben. Just like I am, he’s a Pirates fan who wants to see championships come to Pittsburgh.”

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