Boston Red Sox Rumors: Roy Oswalt a Must-Have, so Sox Need to Deal with Theo

Matt TruebloodSenior Analyst IJanuary 16, 2012

PHILADELPHIA - AUGUST 13: Starting pitcher Roy Oswalt #44 of the Philadelphia Phillies throws a pitch during a game against the Washington Nationals at Citizens Bank Park on August 13, 2011 in Philadelphia, Pennsylvania. The Phillies won 11-3.(Photo by Hunter Martin/Getty Images)
Hunter Martin/Getty Images

The Boston Red Sox have fallen a step back of the pack in the American League. After the New York Yankees' dual pitching additions on Friday and pending final touches to the rosters of the Tampa Bay Rays, Los Angeles Angels of Anaheim and Texas Rangers, the Sox are Roy Oswalt shy of contending seriously next season.

Oswalt is hardly out of reach for the Red Sox. They are his most logical remaining suitor, especially now that the Yankees have Hiroki Kuroda on the books. Unfortunately, it seems the Sox need to clear payroll space before they can make a deal with Oswalt happen, according to WEEI in Boston. Presumably, that dictate comes from ownership, and is not so much about pure monetary savings as about avoiding paying MLB's luxury tax.

It might also be true that the Sox would prefer to reload a bit after a sour ending to the 2011 season, and that they view acquiring Oswalt as a poor process move. It's possible they would prefer to keep the players they might need to deal in order to pay Oswalt, as insurance against injuries and in order to accommodate an unhurried developmental calendar for players like Jose Iglesias and Ryan Kalish, Drake Britton and Stolmy Pimentel.

If that's their choice, so be it. But, color me skeptical. It's not as though the team's most expendable medium-salary assets are also long-term propositions. Since Marco Scutaro and Bobby Jenks are each due to be free agents after 2012, trading them would not damage the 2013 roster in the slightest. Meanwhile, adding Oswalt could make the team a very realistic pennant contender again.

Therefore, GM Ben Cherington needs to find the best move available and deal Jenks in order to make room for Oswalt on the ledger. As it turns out, his best bet may be to turn to an old friend.

CHICAGO, IL - OCTOBER 25:  Theo Epstein, the new President of Baseball Operations for the Chicago Cubs, speaks during a press conference at Wrigley Field on October 25, 2011 in Chicago, Illinois.  (Photo by Jonathan Daniel/Getty Images)
Jonathan Daniel/Getty Images

Theo Epstein bolted Boston for the Chicago Cubs in October, and without objection, both teams have repeatedly postponed the decision on how the Cubs will compensate the Sox for that loss. Now is the time for the Red Sox to rekindle those discussions.

The Cubs have money, and plenty of it. They will run a 2012 payroll somewhere in the range of $110 million, down $25 million from 2011, and after that, more big salaries come off their books. They would have no issues with taking on Jenks at $6 million for 2012, if it got them off easier with the Sox at the bargaining table.

Of course, the Sox can't simply sell Jenks to the Cubs, or his salary counts against the luxury tax for them anyway. Ditto a move where the Cubs simply send the Sox money for Epstein, but leave Jenks on the roster.

The smart answer would be for the Sox to pick from among a large crop of live but uninspiring arms in the Cubs' system, and for the Cubs to swap that player for Jenks' services. The spirit of the deal would dictate a player like Alberto Cabrera, whom the old guard of the Cubs' front office loved but whose only skill is tremendous velocity. 

So it shakes out to this: The Sox get Jenks off the books, add Oswalt and stash Cabrera in Double-A as a potential bullpen clean-up guy if injury strikes during the year. The Cubs get an extra arm for the bullpen, easing the pressure to use Rafael Dolis or Chris Carpenter more than they are ready to be used at the big-league level, and are released from Boston's debt regarding Epstein. As win-win deals go, it would be an ugly one, but it would be win-win, nonetheless. The biggest hangup might be getting Jenks healthy enough to pass a physical.