Ben Cherington's parting gift to Boston

It's probably still too early for a final verdict on Ben Cherington's tenure as General Manager of the Boston Red Sox. Before departing in August of 2015, he had been a member of the team's Baseball Operations department for World Series wins in 2004 and 2007, and GM for a third championship in 2013. He also presided over three last-place seasons in four years, bad for any team and extremely bad for one with the resources and payroll of the Red Sox. He departed having developed a deep and robust farm system, one that has already paid dividends in the forms of Mookie Betts and Xander Bogaerts, and will likely continue to do so for several years.

But the immediate causes of his departure, the actions that had the most impact on the 2015 and 2016 versions of the Red Sox and what most people will think of when they think of Cherington, were the disastrous series of transactions that occurred in the twelve months prior.

At the 2014 trade deadline, John Lackey, who went on to give the Cardinals between 2 and 4 WAR while playing for the league minimum in 2015, was traded for Allen Craig, owner of a 61 wRC+ over the last two years and due $21m over the next two years, and Joe Kelly, signed for three more seasons but maybe not a legitimate starter. Yoenis Cespedes, who produced between 6 and 7 WAR last year for the Tigers and Mets, was traded for Rick Porcello, who was promptly signed to a four-year/$82.5m extension and just as promptly stopped pitching well.

And that's just the trades! Rusney Castillo was signed out of Cuba to a seven-year/$72.5m deal, and he had a 72 wRC+ last season and is en route to being platooned in the outfield. And finally, and most famously, the Red Sox under Cherington signed both Pablo Sandoval and Hanley Ramirez, the former to a five-year/$95m deal and the latter to a four-year/$88m. I'm sure you know how that went, but as a refresher, they combined for -3.8 fWAR and -2.5 WARP. Not good!

When you list those transactions one after another, it becomes pretty clear why Cherington was replaced in somewhat unceremonious fashion. But there's a silver lining, if only with regards to Ramirez, and I'm not just talking about the chance that he is in fact a passable first baseman whose terrible 2015 was just the result of a shoulder injury. No, I'm talking about the length of his contract.

At the outset of the 2014 offseason, Ramirez was one of the most sought after free agents, and the contracts estimated by various baseball writers reflected that. In his profile of Hanley, Zach Links at MLBTradeRumors.com estimated a six-year/$132m deal, while in his free agent predictions, Dave Cameron of FanGraphs (in picks he admitted were "probably going to be hilariously wrong") went with a seven-year/$140m contract for Ramirez. It was somewhat surprising, therefore, when the Red Sox announced they had signed him to a four-year/$88m deal, with a vesting option for the fifth year at an additional $22m should he reach 1,050 PAs between 2017 and 2018.

It's impossible to know what counteroffers Cherington had to beat, or whether Ramirez took something less than the best offer in-hand to return to Boston. Regardless, Boston ended up with a shorter contract than expected, at the cost of a higher annual average value. The downside of such a contract is that extra cash output, but the upside is a smaller disaster should the player lose value more quickly than expected.

To illustrate this, consider two contracts. The first is what Ramirez actually signed, for five years and $110m (assuming he hits the vesting option, which seems probable), while the second is longer, for seven years and $126m. That alternate contract isn't arbitrary – prior to the 2015 season, Ramirez was projected for roughly 3.3 WAR (by Steamer, 3.3 WAR; ZiPS, 3.0 WAR; PECOTA, 3.4 WAR; and the FanGraphs crowdsourced projections, 3.5 WAR). Those obviously had huge error bars, given his move to a new position, and it's easy in hindsight to say they were too optimistic, but I think 3.3 WAR is a reasonable estimate of what the Red Sox thought they were getting. With Ramirez already over the age of 30 and showing signs of injury-proneness during the 2014 and 2015 offseason, I think it's also reasonable to use an annual 0.5 WAR decline for the length of the contract. Finally, I used a 4 percent inflation figure to calculate the net present value of the contract, the same rate the league and the MLBPA have agreed to use for such calculations. With those assumptions, these two contracts have essentially the same value.

The actual contract costs the Red Sox an additional $18.5m in present value through the first five years, but in exchange, they don't spend the $28.8m in present value the other contract tacks on for 2020 and 2021, when this simple setup projects Ramirez to produce only 1.1 WAR. The first contract spends $101.5m in present value for 11.5 WAR, or $8.8m/WAR; the second spends $111.8m in present value for 12.6 WAR, or $8.9m/WAR. In other words, with these assumptions, the Red Sox would have been nearly indifferent between these two contracts.

After 2015, however, that projected WAR column looks pretty silly, and the benefits to the team of a shorter contract become clear. The following table instead uses Ramirez's actual 2015 WAR (-1.8 at FanGraphs, -1.1 at Baseball Prospectus, so I'm using -1.5) and his projected 2016 WAR (2.0 by Steamer, 1.9 by ZiPS, 1.9 by PECOTA, and 1.3 by the FanGraphs crowdsourced projections, so I'm using 1.9), with the same annual decline of 0.5 WAR. (I didn't go below 0 WAR, assuming that a team can always choose not to play a below-replacement level player if it's in their best interests.)

The total WAR produced in the contract plummets, but the balance also shifts in favor of the shorter contract. By paying a higher AAV early in the contract, they get out of two years where Ramirez is projected to produce zero value, and is still owed $28.8m in present value under the longer contract. The former costs $101.5m in present value over five years for 3.1 WAR, or $32.8m/WAR; the latter, $111.8m in present value over seven years for 3.1 WAR, or $36.0m/WAR. To line up the $/WAR, the longer contract would have to fall to about $114m, or $16.3m annually.

The above also assumes Ramirez does in fact reach 1,050 PAs in 2017 and 2018. If his decline looks something like this, and he continues to struggle with injuries, the Red Sox might end up with a four-year contract instead. I won't replicate the table again, but in that case, they'd be estimated to pay $82.9m for 2.7 WAR, or $30.7/WAR, and the longer contract would have to fall to about $107m, or $15.3m annually, to have the estimated same dollar-per-WAR value.

It's futile to try to trace back the cause of the contract being this length. Maybe it was Ramirez's idea, and the Red Sox wanted to go longer; maybe no other team had an offer longer than four years on the table; maybe it's something else entirely. With that in mind, it's probably not worth giving Cherington too much credit for the contract structure that appears likely to save the Red Sox millions of dollars, but he could use a boost. I mean, goodness, in 2014, he also signed Stephen Drew to play two-thirds of a season for $10m! Give him this, if nothing else.

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Henry Druschel is a Contributor at Beyond the Box Score. You can follow him on Twitter at @henrydruschel.