3 Potential Major Deals Ben Cherington Should Propose at the Deadline

Ben CarsleyContributor IMay 16, 2014

Miami Marlins' Giancarlo Stanton, right, reacts after he struck out during the eighth inning of a baseball game against the Los Angeles Dodgers on Tuesday, May 13, 2014, in Los Angeles. (AP Photo)
Uncredited/Associated Press

If the Boston Red Sox are to repeat as World Series champions, there's a good chance that they will need to acquire help from outside of the organization.

It's a strategy they've employed frequently throughout the years, including in their three recent championship campaigns in 2004, 2007 and 2013. Way back in 2004, the Red Sox redefined their franchise by trading away homegrown superstar Nomar Garciaparra and acquiring Orlando Cabrera, Doug Mientkiewicz and Dave Roberts.

JOE GIBLIN/Associated Press

In 2007, Boston made a less prominent and utterly unsuccessful trade for Eric Gagne. And in 2013, the Sox bolstered their pitching staff by trading defensive whizz Jose Iglesias for mid-rotation staple Jake Peavy.

Those three deals run the gamut as far as organizational impact goes—the Nomar trade changed the face of the franchise, the Peavy trade was significant but far less drastic and the Gagne trade was a fairly minor move. The 2014 Red Sox, with their post-Nick Punto trade financial flexibility and enormously talented farm system, have the option of pursuing any type of trade, big or small.

Yet while there's a very sound argument to be made for retaining organizational depth and "letting the kids play," this iteration of the Red Sox may need a major infusion of impact talent if they're to keep their repeat dreams alive.

They have lost a premium talent in Jacoby Ellsbury. They have lost an excellent veteran shortstop in Stephen Drew. They lack a second top-of-the-order arm to pair with Jon Lester, as Clay Buchholz is utterly unreliable at this point. And they lack a third significant power bat to group with David Ortiz and Mike Napoli.

That's why the time may be right for the Red Sox to make a major franchise-defining deal at the deadline, rather than settle for a modest upgrade or shoring up mild deficiencies. Boston has the money, they have the prospects, and they still have the nucleus of a team that can win in 2014.

With that in mind—and because it's just good fun—let's take a look at three potential major deals Ben Cherington should put on the table near the deadline, and how they'd change the course of the Red Sox franchise.


Red Sox Trade Mookie Betts, Allen Webster, Blake Swihart, Drake Britton and Cash to the Philadelphia Phillies for Cliff Lee

"Lee to the Red Sox" trade rumors have been around for a while now, and in truth they make quite a lot of sense. The Phillies have one of the oldest teams in the majors, lack impact talent in their farm system and are headed for another disappointing season, as they currently sit four games under .500. They've committed enormous financial resources to Lee, Cole Hamels, Ryan Howard, Chase Utley, Jonathan Papelbon and Jimmy Rollins, among other players. They need an infusion of young talent and some salary relief.

Enter the Red Sox, who can both give the Phillies the young players they desire and take on a good portion of the $52.5 million Lee could potential earn from 2015-2016. Boston can get Philadelphia to eat some of Lee's contract by offering three Top 100 prospects, yet can also retain some of its elite MiLB talent in Matt Barnes, Henry Owens and Garin Cecchini, plus a 2015 contributor in Christian Vazquez.

Lee would pair with Lester atop Boston's rotation to form one of the best one-two punches in the game, as the left-hander is still one of baseball's best starters despite his age of 35. While absorbing his contract would put a good dent into Boston's financial flexibility, it may not preclude them from resigning Lester after the season when the likes of A.J. Pierzynski and Jake Peavy come off the books and John Lackey's salary is greatly reduced.

There's a good argument to be made that the Red Sox should either retain their prospects or only deal them for younger MLB talent, but Lee is one of the few true impact pitchers who should be readily available this summer. The Sox likely aren't going to hit their way to the top as they did in 2013, so they may need to pitch their way there instead.


Red Sox Trade Garin Cecchini, Matt Barnes, Rubby De La Rosa, Deven Marrero and Anthony Ranaudo to the San Diego Padres for Chase Headley and Ian Kennedy.

The last time the Red Sox and Padres made a major trade, Boston shipped Casey Kelly, Anthony Rizzo and Reymond Fuentes across the country for a talented first baseman by the name of Adrian Gonzalez. It’s a move that worked out strangely for both teams, as San Diego was able to flip Rizzo for Andrew Cashner, while Gonzalez was the centerpiece of the Red Sox-Dodgers trade that gave the Red Sox franchise new life, financially.

This time, the Red Sox get an established veteran at the hot corner and a mid-rotation starter in return for some of their excess prospect depth in a deal that would make a ton of sense for both teams.

Gregory Bull/Associated Press

Headley is a free agent after the season, and while poor performance and injuries have sapped much of the trade value he held a year ago, it's hard to imagine he wouldn't be an upgrade over Will Middlebrooks this year. Kennedy would allow the Sox to either temporarily bump Clay Buchholz from the rotation or to make a more permanent upgrade form Felix Doubront. He'd also give the Sox some rotation insurance for next season, as Peavy and Lester will both be free agents after the year.

The Padres, meanwhile, get their immediate replacement for Headley in Cecchini, and Barnes could thrive in Petco Park. Marrero is a decent shortstop prospect, De La Rosa a potential future closer and Ranaudo can be converted to a reliever thanks to the depth in the Padres system.

Kennedy isn't a great fit for Fenway Park and the Sox may decide not to retain Headley's services after the season, so this isn't quite a perfect deal for Boston. Yet if the Sox want to solidify both their offense and rotation come July, this is a way to do so.


Red Sox Trade Mookie Betts, Henry Owens, Blake Swihart, Allen Webster, Will Middlebrooks and Anthony Ranaudo to the Marlins for Giancarlo Stanton

Let’s get one thing straight—if I’m the Marlins, I don’t accept this deal. The only thing the Red Sox can offer me that makes me consider dangling Stanton is Xander Bogaerts, and there’s no way Bogaerts is available. For that reason, I think the frequently cited Stanton-to-Boston deal we all love to speculate on will never get off the ground.

But this is a column about deals Cherington should offer, and while he’d be hurting Boston’s organizational depth here, the Red Sox would also land a generational talent still entering his prime.

Stanton could sit between Ortiz and Napoli to form one of, if not the, best middle-of-the-order combos in the majors. Placing a player with Stanton's arm in left field at Fenway Park would turn a ton of "wall-ball doubles" into outs at second base. And Stanton gives the Red Sox another long-term piece to build around with Bogaerts and Bradley Jr.

Losing all those top prospects hurts, to be sure, but the Red Sox would still be quite wise to make this offer. In this scenario, Barnes and Brandon Workman would remain to serve as rotational depth, Vazquez still factors in to the future catching situation and the Sox still have bullpen help in Britton and Rubby De La Rosa down on the farm. Cecchini could take over at third base for the Red Sox immediately.

The Marlins may not like not getting Bogaerts, but unless the Pirates give up Gregory Polanco, the Rangers trade Jurickson Profar or the Cardinals send Oscar Taveras, Miami simply isn't going to get a Bogaerts-like talent from anywhere. At least in this deal they diversify their risk while also adding some high-ceiling and high-probability players. It's a long shot, but it's a fun trade to think about nonetheless.

Odds are, the Red Sox will not make such dramatic moves at the deadline this year. While they are likely to bolster their roster, the Sox have worked hard to construct the organizational depth they have today, and that's something they're not going to want to lose in one fell stroke.

But unless the Red Sox see improvement from the likes of Bogaerts, Bradley Jr., Middlebrooks and Buchholz, they very well may not have enough talent to return to the playoffs this season. There's still plenty of time for each of those players to pick up the pace, but an infusion of significant talent could go a long way for this roster all the same.