Red Sox's Josh Hamilton Choice Will Be Career-Defining Moment for Ben Cherington

Zachary D. Rymer@zachrymerMLB Lead WriterNovember 21, 2012

BOSTON, MA - AUGUST 25:  Ben Cherington, general manager of the Boston Red Sox, pauses as announces a trade between the Boston Red Sox and the Los Angeles Dodgers during a press conference at Fenway Park on August 25, 2012 in Boston, Massachusetts.  The Red Sox traded Josh Beckett, Carl Crawford, Andrian Gonzalez and Nick Punto for Dodgers players James Lonely, Ivan DeJesus Jr., Allen webster, and two others to be named later. (Photo by Jim Rogash/Getty Images)
Jim Rogash/Getty Images

Remember when Theo Epstein traded Nomar Garciaparra to the Chicago Cubs in July of 2004? Remember how that felt like a move that was either going to make or break his career?

Current Boston Red Sox general manager Ben Cherington is facing a situation sort of like that one this winter. He has a decision to make on slugging free-agent outfielder Josh Hamilton, and there's no overstating the importance of it.

Exactly how interested the Red Sox are in Hamilton varies depending on who you ask. For example, Jon Heyman of reported last week that he had heard from a rival GM that the Sox seemed to be planning something big and that it wouldn't be a surprise if they got in on the possibly former Texas Rangers star.

Later on that very day, though, Rob Bradford of reported that Boston's apparent interest in Hamilton was being "overblown."

Cherington has been careful not to tip his hand, as any GM should be in any situation. He did, however, confirm in a radio interview on WEEI last week that discussions have been held with Hamilton's agent. He also assured that the Red Sox's 2013 payroll will be "amongst the larger payrolls in the game."

And on Tuesday, Cherington told this to Jim Bowden of ESPN and SiriusXM radio:

Ben Cherington told us that they are still pursuing FA Josh Hamilton calling him " a terrific talent" SXM 209/89

— JIM BOWDEN (@JimBowdenESPNxm) November 20, 2012

The Hamilton-to-the-Red Sox rumor feels like a rumor that shouldn't exist, or a rumor that should have died a quick death as soon as it emerged. But this isn't the case. It has become the horror movie villain of offseason baseball rumors. It just won't die.

At the very least, what we know is that Hamilton isn't entirely off Boston's radar, and we know that Cherington has given the notion of signing him some thought. The Red Sox are thus in a position to go through Door No. 1 or Door No. 2 in regard to Hamilton. One is labeled "To sign" and the other is labeled "Not to sign."

Either way, Cherington will be making the biggest decision of his career. This will be it. The big one. His masterpiece or his doom.

And given all he's been through in his one year on the job, this is saying a lot.

Cherington has already made a ton of tough calls since taking over for Epstein last October. His first order of business was an ill-fated managerial search that ultimately culminated in the hiring of Bobby Valentine, who, apparently, was not Cherington's pick for the job.

Then came spring training, which brought with it the Daniel Bard experiment. Then came the regular season, early on in which Cherington was forced to make a tough call on Kevin Youkilis.

By July, the Red Sox were falling apart, and Cherington had to decide to buy, sell or stand pat at the trade deadline. He chose to do very little in the end, but he pulled off one of the biggest trades in baseball history just a few weeks later when he sent Josh Beckett, Carl Crawford, Adrian Gonzalez and around $250 million in salaries to the Los Angeles Dodgers.

Not too long afterward, Ken Rosenthal of was kind enough to let everyone know that Cherington had passed on a chance to acquire Joe Mauer from the Minnesota Twins via a waiver claim. He could have been very tempted to do so, but he was able to stay his hand.

So in a span of a couple days—seriously, a couple days—Cherington thus proved to the world that he had the boldness to know when to make a big move and the discipline to know when not to make a big move.

Now here's Hamilton in front of Cherington, and he must once again decide whether to be bold or to be disciplined. He stands to gain much by being bold but also to lose much. By being disciplined, he stands to watch tremendous success or tremendous failure pass the Red Sox by.

Gambling on Hamilton is awfully tempting, as the Red Sox have more excuses to sign him than any other team in baseball.

They need a starting left fielder, not to mention a left-handed power bat in their lineup to take the place left vacant by Adrian Gonzalez. With so much of their former payroll now in Los Angeles, the Red Sox also have more than enough financial flexibility to sign Hamilton to the lucrative contract he's known to be seeking.

Hamilton is a career .304/.363/.543 hitter with 40-homer power who won an MVP on the strength of a league-high 1.044 OPS a couple years ago. If that's the player the Sox got after signing Hamilton, Cherington would be widely praised for having the guts to give him a contract. Where other GMs were afraid to tread, he proceeded fearlessly and was awarded greatly.

But we also know all about the potential disaster that may await the Red Sox if they do sign Hamilton. As I wrote the other day, signing him could actually end up being worse for the Red Sox than the Carl Crawford signing, as the warning signs are there that Hamilton is A) a hitter on the decline, B) a player who comes with too many injury concerns and C) a bad fit for the high-pressure Boston environment.

If the Red Sox were to sign Hamilton and subsequently see all their worst nightmares come true, Cherington would surely not escape blame. Hamilton's contract would reflect just as poorly on him as Crawford's does on Epstein, or as poorly as Alfonso Soriano's contract still reflects on Jim Hendry, or as poorly as Vernon Wells' contract still reflects on J.P. Ricciardi.

Neither Hendry nor Ricciardi is currently serving as a general manager at the moment. Both are special assistants to GMs, a demotion that Cherington could have to deal with some day if he were to sign Hamilton only to see the signing blow up in his face. We're talking about a move that could kill his career just as easily as it could make it.

Passing on Hamilton, meanwhile, comes with an entirely different set of consequences.  

If Cherington were to pass on Hamilton only to see him go on and find great success with another team, he'd have to put up with an outcry from Red Sox fans over why the club wasn't more aggressive in its pursuit of Hamilton.

"Just look at what we're missing out on!" they'd say, and they would not be quelled by explanations of how signing Hamilton was too risky to mesh with the club's desire to be more disciplined. Especially not, of course, if the Red Sox are losing while Hamilton's new club is winning. 

But then there's the scenario that involves the Red Sox avoiding the very disaster that so many of the club's fans are worried is going to take place if Cherington does sign Hamilton. The Sox could pass on Hamilton and then watch him go elsewhere and fall flat on the field, pick up old bad habits off the field or do both at the same time.

One's first instinct is to assume that an outcome such as this would result in praise for Cherington. But would it really?

After all, it's not like he would come out and brag about how he had a chance to sign Hamilton and didn't. The reasoning and the time line for his decision to pass on Hamilton would more than likely stay behind close doors, perhaps to be revealed at a much later date.

Plus, choosing to pass on Hamilton and watching him fail elsewhere wouldn't necessarily be a total victory for the Red Sox. Cherington could pass on Hamilton and then pass on making any big moves in general this winter.

His unwillingness to make a splash could lead to a down year for the Red Sox in 2013. If so, Red Sox Nation surely wouldn't accept that doing nothing was the right alternative to signing Hamilton.

Then again, it obviously shouldn't be assumed that doing nothing is an actual alternative to signing Hamilton. Cherington could take the $25 million or so per year he has the option of committing to Hamilton and commit it to another star player or a series of quality ballplayers.

This is a plan that could already be taking shape with the Red Sox's signing of Jonny Gomes, which Susan Slusser of the San Francisco Chronicle says is just about done. Up next could be a reunion with Cody Ross, a low-risk starting pitcher.

If Cherington passes on Hamilton and builds a contender on a budget instead, he'll be praised accordingly. Fans love general managers who can build winning teams for cheap, a la Billy Beane and Andrew Friedman. They'll go absolutely wild for a GM who managed to build a contender for cheap despite having the considerable financial resources of the Boston Red Sox at his disposal.

So despite the fact there are only two doors to walk through regarding Hamilton, Cherington stands to earn one of several possible reputations from his decision. He could become the ultimate lucky gambler GM, the ultimate fool GM, the ultimate overly cautious GM, the ultimate underappreciated GM or the ultimate genius GM.

For the time being, we really don't know what kind of reputation best suits Cherington. He only has one disastrous season under his belt, but it wasn't really of his making, and the best move he made all year was a trade that destroyed the roster.

As soon as that trade was given the green light, Cherington was effectively given a green light to remake the Red Sox as he saw fit. From here on out, it's all on him. 

A few years from now, we're going to know what kind of GM Cherington is (or was), and there's no escaping the notion that it will all trace back to the decision he made on Josh Hamilton.


Note: Stats courtesy of unless otherwise noted. 


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