The Biggest Thing Ben Cherington Brings To The Table

The Pirates will enter this offseason with a new Team President, GM, and manager. That’s a lot of change. But a lot of things will remain the same. Mainly the payroll.

But there’s still reason for a slight degree of optimism. Long-term optimism.

Drafting and developing prospects means the world to a small-market team. Luckily for the Pirates, new GM Ben Cherington has a good track record of doing just that.

In the beginning of Neal Huntington’s reign, the Pirates’ farm system was consistently ranked in the top tier of the league. Over the last 5-6 years, a lot of those pieces (headlined by Gerrit Cole, Austin Meadows, Jameson Taillon, Tyler Glasnow, and Josh Bell) graduated the farm system and now the Pirates prospects pool is ranked in the lower half of the league.

In my opinion, the biggest reason for Huntington’s dismissal was how he mismanaged the farm system. A lot of names didn’t develop nearly as well as the organization would have hoped. And others are performing much better for other teams than they did in Pittsburgh.

But that’s in the past. The most-realistic strategy for a successful Pirates rebuild is to focus on the farm system. Draft well and develop better. Looking at some past examples, I like having Cherington leading this initiative.

Cherington took over for Theo Epstein as the Red Sox GM after the 2011 season when the team was in disarray. New manager. Veteran core is getting old. He led the team to a World Series title two seasons later on the backs of his veteran free agent signings of Shane Victorino, David Ross, Jonny Gomes, Koji Uehara, Mike Napoli, and others.

Yes – the Sox did follow up the 2013 title with back-to-back last place finishes in 2014-15. Those failures were mainly because of bad mega-contracts with Pablo Sandoval and Hanley Ramirez.

And to that I say this…

And during those failures which led to him leaving the team, we see Cherington’s biggest success.

Despite not being with the team since 2015, Cherington had a big say in the Red Sox 2018 championship. Why? Cherington built that core. In addition to a few other pieces, AL MVP Mookie Betts, Xander Bogaerts, Andrew Benintendi, and Jackie Bradley Jr. were all players that were either drafted or developed under Cherington. Additionally, a lot of the big trades that Dave Dombrowski made to strengthen the 2018 team were possible because of the prospects Cherington drafted and developed.

After leaving the Red Sox and taking a year away of the game, Cherington was hired by the Blue Jays in 2016 to act as their Vice President of Baseball Operations. In those three years before being hired in Pittsburgh, he spearheaded the team’s efforts in rebuilding a barren farm system. And now, Toronto has one the league’s better farm systems. Their future outlook is promising.

Pittsburgh hasn’t drafted or developed well in the last several years. That’s why they are where they are. As much as it may hurt, I expect Cherington to look to move any piece not named Reynolds, Keller, or Newman as we enter a new era in Pirates baseball.

This team doesn’t have the pieces or ownership’s wallet to reload. Time to release current talent, rebuild the farm system, and #TrustTheProcess.

That’s the team’s most effective route back to contention.

Go crazy, Cherington.

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