Will the Boston Red Sox Trade for Cliff Lee and Justin Upton This Winter?

Ian Casselberry@iancassMLB Lead WriterAugust 30, 2012

Would the Red Sox take on the possible $100 million remaining on Cliff Lee's contract?
Would the Red Sox take on the possible $100 million remaining on Cliff Lee's contract?Justin Edmonds/Getty Images

What will the Boston Red Sox do this winter?

After their mega-trade with the Los Angeles Dodgers cleared $260 million off the team payroll, general manager Ben Cherington has many more possibilities available to him than he did a week ago. Boston has a couple of months to map out its offseason plan and decide which players to target.

Throwing big money at a free agent would run contrary to the presumed new direction of the Red Sox front office. Why tie up payroll again with big contracts after creating flexibility by shedding so much salary? Under those circumstances, pursuing marquee free agents like Josh Hamilton or Zack Greinke seems unlikely.

But what about making a big trade or two? In predicting what the Red Sox might do this offseason, ESPN Boston's Gordon Edes highlighted two players the team could pursue. Could Cherington go after Cliff Lee as a top-of-the-rotation starter to pair with Jon Lester? What about Justin Upton to fill the team's hole in right field?


Chasing Cliff Lee

Does Philadelphia Phillies GM Ruben Amaro Jr. want to trade Cliff Lee? The suspicion here is that he does. Though rumors may have been created to generate buzz around the July 31 trade deadline, there were too many rumblings surrounding Lee to think that the Phillies weren't shopping him around the league. 

The Los Angeles Dodgers put Amaro on the spot by claiming him on waivers on Aug. 3. Just how badly did the Phillies want to get rid of the $95 million remaining on Lee's contract at the time? Lee is owed a possible $102.5 million through 2016. That's money Amaro could use to fill other holes on his roster, such as the outfield and third base. 

The Dodgers and Phillies didn't agree to a deal before the waiver claim expired. Presumably, the Phillies wanted top prospects in return, but the Dodgers were hoping to avoid giving up that kind of talent by taking on the full remaining value of Lee's contract. 

Amaro has the time to work out a better deal during the offseason, however.

Lee's contract is still a big one to move. He's owed at least $87.5 million if his 2016 option isn't picked up. But any team looking for a top starting pitcher would likely have to pay more than that and offer more years on a contract through free agency. 

That makes Lee a suitable target for the Red Sox if they want to add a top starting pitcher. His 2012 numbers don't look terribly impressive with a 3-7 record and 3.67 ERA in 23 starts. But Lee has pitched much better since a terrible June during which he went 0-3 with a 6.12 ERA.

There are some concerns when looking at Lee's season numbers. He's allowing more hits and home runs per nine innings than he has in the past four years. Yet he also leads the majors with a walk rate of 1.4 per game. Perhaps his control has been too good and he's leaving too many pitches in the strike zone to be hit.

Something else to consider is that Lee has received poor run support from the Phillies lineup this year. Philadelphia is among the bottom third of major league teams in runs scored. That wouldn't be a problem in Boston, where the Red Sox have scored the second-most runs in baseball this season. 


Upton a Perfect Fit in Boston

Arizona Diamondbacks GM Kevin Towers wants to trade Upton. In his two years heading the D-Backs front office, Towers has been rather public about his willingness to deal off the 25-year-old right fielder. 

Whether it's because he doesn't like Upton's game or is intrigued by the bushel of prospects Upton could fetch in a deal, Towers has made too much noise about trading Upton to think he won't do it during the offseason.

The Red Sox need a right fielder for next season. Actually, it's been a hole on the roster all year. Upton has three years remaining on his contract worth $38.5 million. Boston isn't going to find an impact outfielder for that kind of money and contract length in free agency.

Nick Swisher, for example, is reportedly hoping to get a four- or five-year deal worth $15 million per season on the open market. Even if he pays dividends on and off the field early in the contract, do the Red Sox really want him on their roster by the time he's 35 or 36 years old? Upton will still be only 28 when his contract expires. 

Though the general perception is that Upton is having a down year, he's hitting a respectable .276/.357/.410. But the concern is with his power numbers. Upton has only 11 home runs this season. His slugging percentage is .410. 

ESPN.com's Mark Simon highlighted several of the problems plaguing Upton this season. He's hitting fewer balls in the air and pulling the ball less. Does that indicate a timing issue with his swing? Has he lost any bat speed due to bulking up, as ESPN.com's Jerry Crasnick noted from an AL scout? 

Perhaps having a batter like David Ortiz hitting behind Upton would make a difference in the kinds of pitches he sees. Though Chase Field is actually a slightly better hitters' park than Fenway Park (according to ESPN.com), maybe a change of scenery would benefit him.

Upton also wouldn't be looked upon as a leader in Boston with Ortiz and Dustin Pedroia in the clubhouse. That could relieve some of the burden he might be dealing with in Arizona. 

Most importantly, adding Upton would make the Red Sox lineup younger and more athletic—two aspects that were lacking in the lineup that was in place before the trade with the Dodgers. This is presumably another reason Cherington wanted to overhaul his roster. 

The Red Sox have the prospects to get both Lee and Upton, even more so after the haul they received from the Dodgers in return for Adrian Gonzalez, Josh Beckett, Carl Crawford and Nick Punto.

Both the Phillies and D-Backs are seeking middle infielders. Boston has shortstops to spare in Jose Iglesias, Pedro Ciriaco and Xander Bogaerts. Outfield prospects like Bryce Brentz and Jackie Bradley would surely be appealing as well. And of course, teams are always looking for pitching. Cherington can now dangle Rubby De La Rosa or Allen Webster in a potential deal. 

The misconception about the Red Sox after their big trade with the Dodgers is that they could be undergoing a semi-rebuilding project. With the right additions, this team could easily compete in the AL East next season. Two excellent options could be available if the Red Sox are willing to deal. 


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