Jacoby Ellsbury’s Reported Signing Represents an Ill-Advised Act of Desperation by Yankees

Jacoby EllsburyHats off to the Red Sox for standing up from the table, pushing in their chair and heading over to the nearest cashier.

As the always soulful Kenny Rogers once said, “You’ve got to know when to hold ‘em, know when to fold ‘em.” And when it came to Jacoby Ellsbury’s contract negotiations, the Red Sox understandably weren’t willing gamble, whereas the Yankees frantically let it ride in an ill-advised act of desperation.

No one is disputing that Ellsbury is a dynamic player whose presence should make the Yankees a better team. But when it comes to today’s business of baseball, the Red Sox have the right idea, while the Yankees are, well, being the Yankees, which in this particular instance involves shelling out the third-largest contract ever given to an outfielder to a player who — despite his immense talent — comes with some questions.­ (Manny Ramirez and Matt Kemp are the only two outfielders to earn bigger contracts in terms of total dollars.)

Ellsbury’s biggest asset is his speed. It’s reasonable to think that he won’t be as fleet-footed in 2020 (when his reported deal expires), although as FanGraphs’ Dave Cameron points out, players with Ellsbury’s skill set typically age well in their 30s. Regardless, even at his peak, is Ellsbury worth close to $22 million per season?

The answer — at least in one writer’s opinion — is a resounding “no.” The 2011 version of Ellsbury that clocked 32 homers, drove in 105 runs, hit .321 and swiped 39 bags is worthy of such a salary, but that campaign looks like an aberration. While Ellsbury should see an uptick in his power numbers playing in lefty-friendly Yankee Stadium, expecting him to suddenly match his ridiculous 2011 totals as he enters his 30s is lunacy.

Maybe the Yankees think that the real Ellsbury, who is now the 14th-highest-paid player in baseball, is truly worth $153 million over the next seven years. In which case, all the power to them. But the deal also seems like a knee-jerk response to everything that has transpired over the last few months, including reports that surfaced Tuesday stating that Carlos Beltran has a three-year, $48 million offer in hand and could end up signing with the Royals.

In many ways, signing Ellsbury on the heels of signing Brian McCann to a five-year, $85 million contract is similar to the Yankees’ offseason splurge prior to the 2009 season, when New York inked Mark Teixeira (eight years, $180 million), CC Sabathia (seven years, $161 million) and A.J. Burnett (five years, $82.5 million) to deals that totaled $423.5 million. It worked to some extent, as the Yankees captured a World Series title that season, but repeating the feat should be even more difficult this time around. The AL East is stronger top to bottom, the quality of incoming players is lesser — no disrespect to Ellsbury and McCann — and the Yankees still have numerous issues unresolved.

For one, Ellsbury’s signing only complicates matters with second baseman Robinson Cano, who is currently a free agent. The two sides have seemingly been in a pissing contest this offseason, and watching New York sign Ellsbury to a seven-year, $153 million deal is hardly going to make Cano come down on his crazy demands. If anything, it makes his demands seem more reasonable — or least more justifiable at the bargaining table.

Yahoo! Sports’ Jeff Passan reported Tuesday that the Yankees believe they still have room for Cano or free-agent outfielder Shin-Soo Choo and a starting pitcher in the wake of signing Ellsbury. It’s hard to imagine New York getting under the $189 million luxury-tax threshold, though, and going over will result in a penalty — something that Brian Cashman would like to avoid, if possible.

Oh yeah, and there’s the whole draft pick thing. Because Ellsbury and McCann were extended qualifying offers by the Red Sox and Braves, respectively, the Yankees, by virtue of signing both, have now lost their first- and second-round picks for the upcoming draft. It isn’t a massive setback given that the club will recoup draft picks if Cano, Curtis Granderson and/or Hiroki Kuroda sign elsewhere, but stockpiling picks should be a priority for an organization with a depleted farm system, like the Yankees.

Who knows? Maybe Ellsbury will go to the Bronx and evolve into an elite player — not just an elite leadoff man or an elite center fielder — thus rewarding the Yankees for what seems like a wild gamble. But given the surplus of lengthy contracts that have backfired recently, the Red Sox should take pride in their willingness to play things safe, no matter how enticing the idea of keeping Ellsbury in Boston was.

Desperate teams do desperate things, and the Yankees are on tilt right now while the Red Sox are waltzing around the casino in a calm, cool and collected manner.

Have a question for Ricky Doyle? Send it to him via Twitter at @TheRickyDoyle or send it here.

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