First Pitch: Ben Cherington’s History With Free Agency Values is Encouraging

Shane Victorino.

Stephen Drew.

Mike Napoli.

David Ross.

Jonny Gomes.

Koji Uehara.

Ryan Dempster.

$53.1 million dollars.

18.3 fWAR.

Perhaps the greatest set of moves of current Pirates General Manager Ben Cherington’s career came prior to the 2013 season that saw him lead the Boston Red Sox to a World Series title. The big market franchise, with Cherington as their General Manager at the time, had previously leveraged their spending power to get the biggest names and the biggest contracts.

Cherington flipped that approach in 2012, dumping $255 million in future salaries with the trades of first baseman Adrian Gonzalez, center fielder Carl Crawford, starting pitcher Josh Beckett, and second baseman Nick Punto.

Salary dumps are a thing Pittsburgh Pirates fans are familiar with. So is the phrase “financial flexibility.” But Pirates fans don’t often see good execution of the latter following the salary dumps that create the flexibility.

Cherington, fresh off his salary dumps after the 2012 season, did a masterful job of not only replacing who he traded away, but doing so in a much more efficient manner.

Mike Napoli replaced Gonzalez at first base, putting up a 3.4 WAR in 2013 under a one year, $5 M deal. Gonzalez had a 2.4 WAR with the Dodgers.

Shane Victorino replaced Crawford in the outfield, with a 4.7 WAR in 2013 at the start of a three year, $39 M deal. Crawford had a 2.2 WAR with the Dodgers.

Stephen Drew replaced Punto in the infield, with a 3.6 WAR on a one year, $9.5 M deal. Punto had a 1.5 WAR with the Dodgers.

Dempster didn’t perform well on a two year, $26 M deal, putting up only 0.5 WAR in 2013. However, Koji Uehara made up for that with a 3.1 WAR on a one-year, $4.25 M deal. Beckett had an 0.1 WAR with the Dodgers.

Jonny Gomes and David Ross each added 1.5 WAR under two year deals that paid a total of 16.2 million.

In total, Cherington shed $255 million in future salaries from four players who ended up combining for 6.2 WAR in 2013. He then added just under $100 million guaranteed in salaries from seven free agents who combined for 18.3 WAR in 2013.

And the Red Sox won the World Series.

I bring all of this up because it’s exactly what the Pirates will need going forward.

This isn’t a team with bad contracts that need to be shed, but it is a team that can benefit from finding value in the lower-to-middle free agent tiers like Cherington found prior to the 2013 season. The top tier of free agency is a strategy for a team like the Red Sox. It’s an impossibility for a team like the Pirates.

The Pirates will always have to build the core of their winning teams from within. That happened in 2013-15 with the likes of Andrew McCutchen, Starling Marte, Neil Walker, Gerrit Cole, and other young players who boosted the team. The Pirates have some promising prospects making their way through the system, giving them a much better outlook for the 2022-2023 seasons.

Even if a majority of those prospects work out, they’re still going to need help from the outside. They’re going to need to find values via free agency. They can’t afford to spend in the top tier, and they barely can afford the spend in the middle tier.

This is where I’m most encouraged by Ben Cherington’s track record. What the Pirates need most is someone who can develop the talent in the system, then add to that group with shrewd additions on the free agent market. Cherington has shown the ability to do both, with his work in free agency being the highlight of the best year of his career.

Can he repeat the same magic again in Pittsburgh, almost a decade later?

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First Pitch