New Pirates GM Ben Cherington has his work cut out for him

On Monday, the Pirates officially announced the hiring of former Red Sox GM Ben Cherington as their new General Manager. Cherington fills the vacancy left behind by Neal Huntington, who did the job for 12 years and helped the 2013 Pirates break what was then the longest playoff drought in baseball. Cherington takes over a rebuilding team that won only 69 games last year.

When I wrote about the firing of Neal Huntington, I wrote about how unenviable this opening was, and it was not just because of the state of the team, or the middling state of the farm system. Owner Bob Nutting has made it clear that he has no interest in spending on the team, and while teams such as the Rays have shown that it is possible to assemble a highly competitive team on the cheap, it is incredibly difficult to do so. Moreover, Tampa Bay was able to pull that off thanks to being at the forefront of player development, an advantage that the Pirates no longer have. Even if we were not in a player development revolution, the Pirates clearly need help in that area. Just look at what happened when Tyler Glasnow, Austin Meadows, and Gerrit Cole, left the organization.

If, say, the Pirates are in need of a shortstop in two years and choose to go after a 28-year-old Francisco Lindor, there is no reason to believe that Nutting will be willing to spend the $250-300 million it will likely take to sign him. The largest free agent contract in Pirates’ history is the three-year, $39 million contract they gave to Francisco Liriano prior to the 2015 season. The Angels spent almost $37 million this year on Mike Trout alone. The Pirates did not even end up paying more than $21.5 million of that contract, either, because they traded him to the Blue Jays at the 2016 trade deadline. To be fair, though, Liriano had a 6.02 RA9 at the time, and ended up having a 5.58 RA9 over the last two year of that deal.

Why the Astros’ sign-stealing matters

Photo by Tim Warner/Getty Images

MLB must act to prevent a race to the bottom.

Parker White at 12up did a great job of ripping the Pirates’ historical lack of activity in free agency. Pirates fans, I suggest you click on that link only if you are in place where it would be okay for you to start yelling and cursing.

I am probably higher on Cherington as a GM than most, despite the fact that the Red Sox came in last place three times in the years surrounding that 2013 World Series victory.

When he lost his job to Dave Dombrowski in 2015, he left behind the core of a team that was critical in winning the division in the three subsequent years, including a 2018 World Series victory. That 2018 Red Sox team was easily the best in franchise history, and once could make the argument that it was the best team ever.

The famous blockbuster trade with the Dodgers in August 2012 that cleared $262.5 million in salary and brought back prospects was orchestrated by Cherington, and I don’t think it is at all an exaggeration to say that it was one of the best moves executed by an executive this decade. It really was a historically great transaction.

Let’s take a look at some of what Cherington did during his Red Sox tenure.

• He was the Assistant GM when the Red Sox signed Xander Bogaerts, and drafted Mookie Betts and Jackie Bradley Jr. He was the full GM during roughly the last two years of their minor league development.
• He signed Rafael Devers in August 2013, and he might be a superstar.
• He drafted Andrew Benintendi in 2015.
• He traded for Brock Holt, Rick Porcello, and Eduardo Rodríguez.

Unfortunately, Cherington had his share of failures, too.

He signed Hanley Ramírez to a four-year, $88 million to be the team’s new left fielder for 2015. I will still defend him on the process behind the deal, because even a 40-grade shortstop should be at absolute worst a passable corner outfielder, and he was coming off a 2.5-year stint with the Dodgers where he hit .299/.368/.506 over 1,120 PA. Hanley Ramírez was even worse than Manny Ramírez in left field, and he eventually had to be moved to 1B/DH. To make matters worse, he failed to be even average offensively starting in 2017, forcing the Red Sox to outright cut him early in the 2018 season.

The Pablo Sandoval deal at fiver years and $90 million, on the other hand, is harder to defend, and it might be one of the worst free agent signings of the decade based on results. Most were down on the signing when it happened, but I don’t think even the most pessimistic analyst was expecting him to be worth -2.5 WAR total half way through the deal before being cut.

Cherington clearly knows how to build a farm system given his track record in Boston and more recently in Toronto, and he knows how to execute effective trades. Where he is lacking, however, is pulling the trigger on big free agent acquisitions, as well as which free agents are worth bringing in at all. He is basically the perfect choice for a franchise owned by Bob Nutting.

If I were Cherington, I would try very hard to lure talent from the Rays and Astros to help with player development. With the garbage that the Astros have been involved with lately, and how toxic the culture there is reported to be, he might not have to try too hard to hire talent away from Houston. Furthermore, while it does not make sense to try and win games when rebuilding, tanking just is not what it used to be. The Royals lost 103 games this past season and are only picking fourth in the draft.

The Pirates did well in hiring Cherington, but rebuilding is going to be more difficult with this franchise than it would be with just about any other, no thanks to the cheap owner. Personally, I hope this once proud franchise does the memory of Roberto Clemente proud.