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Breaking the (Piggy) Bank: Moving Red Sox Payroll

Roy Oswalt can only roll his eyes knowing that the Red Sox have to move payroll to afford him. (Photo courtesy of USA Today/Getty Images)

When the New York Yankees went ahead and revamped their starting rotation, trading for 23-year-old pitching phenom Michael Pineda and signing Hiroki Kuroda to a one-year deal, they immediately became the favorites to win the AL East again in 2012.

On paper, that is. (Allow me this one glimmer of hope, please and thank you. September 2011 was not kind to me.)

It of course prompted immediate speculation on how the Red Sox would respond. What would rookie-GM Ben Cherington do to answer Boston’s biggest rival? Would the Red Sox continue to sit pat? Would they make a play for Roy Oswalt, purportedly only asking for a one-year contract in the range of $8 million?

According the WEEI’s Rob Bradford, the Red Sox would reportedly have to move payroll in order to meet Oswalt’s contract demands. Yup, the team with player salaries already topping $170 million, the same ownership group that signed off on $142 million worth of Carl Crawford, aren’t willing to take the luxury tax hit. Apparently John Henry maxed out his credit card buying $300 headphones to massage his players’ egos and eardrums.

With Kuroda, Ryan Madson, and Oswalt all available for what amounts to the spare change rolled up in the tarp at Fenway, the Red Sox remain remarkably and ridiculously steadfast (read: stingy) in keeping together a team that squandered a nine-game lead in less than a month. (So the Red Sox are shooting for that newfangled extra wild card spot? Is that it?)

For the sake of argument, let’s say Cherington comes to his senses and realizes how desperately he needs a reliable frontline starter to hedge his bets on Aaron Cook, Carlos Silva, and Vincente Padilla. On a scale of “No Way, José Valentin” to “Manny Being Manny,” who would the Red Sox unload to make the numbers work?

Sawx Foh-evah

Clearly Cherington won’t unload any cornerstones of the franchise, particularly the homegrown talent that has been central to Red Sox success in recent years. That means Dustin Pedroia, Jon Lester, and Clay Buchholz with their long-term, team-friendly deals won’t be going anywhere. Nor will Adrian Gonzalez, who cost the Red Sox a pretty prospect. No way, no how for any of those guys.

If Julio Lugo and Edgar Renteria had a Child…

On the other side of untradeable, these are the terrible players and their monster contracts that not even Frank McCourt pre-divorce would try to take on. I’m talking about you, John Lackey ($15.25 million per year), Carl Crawford ($19 million), Daisuke Matsuzaka ($10 million), Bobby Jenks ($6 million), and yes, even you, Josh Beckett ($15.75 million). They’re all immovable objects, and not just because of their beer guts.

That is, unless Cherington can convince the San Diego Padres to reopen negotiations on John Lackey. But without a Red Sox secret agent at the helm, it may be tough to pull off another heist like the Gonzalez trade (Anthony Rizzo almost lasted a full year before they deemed him a bust!).

Forgive Me, Father, For I Have Sinned

This possibility makes me want to let Carl Everett headbutt me until it makes sense, but it can’t be overlooked: Jacoby Ellsbury.

I’m well aware that he just finished second in the 2011 MVP voting and that he is the sexiest player this side of El Guapo. But his salary arbitration will skyrocket every year if he keeps it up, or he’ll merit a lucrative long-term deal (if Crawford got $142 million, what will Ellsbury command?!). And if the Red Sox can’t even shell out $8 million to Oswalt this year, how do they expect to hang onto Ellsbury in the future? Could it be that they trade him for a serious haul of top-level prospects?

My suspicion (call it a conspiracy theory) is that the Red Sox are actually refusing to go after Oswalt in order to reset their luxury tax payments and reserve that money for signing Ellsbury to a massive extension. Let us pray.

The Real Deals (To Be Made)

Now, obviously the small contract guys like Jarrod Saltalamacchia, Ryan Sweeney, Mike Aviles, Franklin Morales, and company can be written off because they don’t even make a splash next to John Henry’s yacht. Seriously. They probably make as much as Henry’s seaward butlers.

No, the Red Sox have two players they might be able to move to clear space for Oswalt: J.D. Drew Kevin Youkilis and Marco Scutaro. I’ve already outlined why I think Youkilis could make a decent trade chip. To recap, he has value as one of few power-hitting third basemen in the major leagues and is relatively affordable at $12 million this year. The Red Sox could get a decent return on such a trade, and it’s not like he has been extremely reliable on the field or in the clubhouse for Boston the last two years. He’s also 33.

Scutaro is also on the back-end of his career, in the last year of his contract before Jose Iglesias presumably takes over. That makes his $6 million option eminently expendable, with no long-term role on the team. His trade value probably isn’t as high, but Scutaro is a reliable starting shortstop with decent fielding and the second-best batting average among players at his position in 2011.

Who wants to make a deal?

Paper-Thin Dreams

Unfortunately, the Red Sox traded the one player best primed to take over for either Youkilis or Scutaro, shipping Jed Lowrie to Houston for reliever Mark Melancon. Mike Aviles could presumably serve as a suitable replacement for either player, but that would figure to be a significant downgrade offensively.

Still, to essentially trade Youkilis or Scutaro for Oswalt’s consistently sub-4.00 ERA (career 3.21), strong strikeout-to-walk ratio (over 3 to 1), and pedigree as an ace unafraid to pitch under pressure? Might not be a bad idea.

On paper, that is.

About Nick Bohlen - @ndbohlen

Nick is an editor and regular contributor for the Patriots, Celtics, and Red Sox sections of SoB. (Despite growing up in Vermont, just a short drive from Canada, hockey never really caught on with him.) Follow him on twitter: @ndbohlen

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One comment for “Breaking the (Piggy) Bank: Moving Red Sox Payroll”

  1. No to Oswalt he has never pitched in the AL, will be a big bust just like Smoltz & Penny.

    Posted by Martin | January 20, 2012, 8:55 am

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