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A trade revisited: How close was Jacoby Ellsbury for Justin Upton?

11.16.11 at 10:29 am ET

MILWAUKEE — A year ago, the GM meetings were dominated by one name.

Kevin Towers was in his first offseason as general manager of the Diamondbacks. He needed to gauge the market value of his players. That, in turn, meant that no one was untouchable in trade conversations, including his single greatest asset: Outfielder Justin Upton.

Upton was coming off of what was, for him, a down year, hitting .273 with a .356 OBP, .442 slugging mark, .798 OPS, 17 homers and 18 steals in 133 games. But for a player with superstar potential (and, in fact, one superstar-caliber season on his resume in 2009), he was signed to a tremendously appealing contract, a six-year, $51.25 million contract that ran through 2015, when Upton would be just 27. Few players in the game were so young with such strong track records, such bright futures and such appealing cost certainty.

Virtually every team in baseball was interested, and the Red Sox were no different. Indeed, the Sox were as aggressive as any team in the majors in trying to pry Upton from the Diamondbacks.

“That was a team we matched up fairly well with. I don’€™t want to get into who the players were,” Towers recalled on Tuesday. “They certainly had the type of package, the right package, where something could have happened but didn’€™t. Nothing really ever got that close.”

Even so, it is fascinating to revisit the type of players who were discussed, given one of the players whom the Sox were discussing. Jacoby Ellsbury and Daniel Bard were both frequently discussed names in a potential deal. And given Ellsbury’s MVP-caliber season, in which the centerfielder hit .321 with a .376 OBP, .552 slugging mark and .928 OPS with 32 homers and 39 steals while also nabbing a Gold Glove in center field, the most talked about potential deal of last year’s GM meetings remains an intriguing subject of inquiry.

Upton had a monster season, hitting .289 with a .369 OBP, .529 slugging mark, .898 OPS, 31 homers and 21 steals while helping to lead the Diamondbacks to the playoffs. He just turned 24, and he represents an anchor of Arizona’s playoff aspirations for years to come. He is signed for four more years, during which he will still be ascending towards his prime.

Ellsbury, meanwhile, has two more years (in his age 28 and 29 seasons) before he reaches free agency. He is in line for significant pay increases through salary arbitration. The eight-year, $160 million deal that the Dodgers recently reached with Matt Kemp offers some indication of the type of long-term deal that Ellsbury would require if the Sox were to prevent him from reaching free agency.

While Ellsbury had, by virtually any measure, the better season than Upton in 2011 (a remarkable fact given what Upton did for Arizona this year), the contract issue complicates the assessment of whether the Sox or Diamondbacks would have been better off had a trade been consummated. (In that light, it’s also worth noting that Bard, like Upton, is under team control for four more years, and he represents a key figure in the late innings for the Sox, particularly with the departure of Jonathan Papelbon.)

At any rate, the whole thing is simply a theoretical exercise, since Towers ended up holding onto Upton and the Sox kept Ellsbury and Bard.

“I never got very close. It was going to be one of those where it had to be a win deal. But being new to the organization, I had to find out what his value was,” Towers said of his talks about Upton last year. “With San Diego, I had at least 15 years to know, going into every winter, how people valued my players. Arizona, I was kind of going in blind. If a handful of guys are untouchable, I’€™ll never find out, but nothing ever came real close.”

One year later, Towers added, he has no plans to renew his examination of Upton’s value.

“Haven’t had any discussions about him,” he said with a laugh. “And I haven’t heard Ellsbury’s name, either.”

Read More: Arizona Diamondbacks, Daniel Bard, Hot Stove 2011, Jacoby Ellsbury
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