Boston Red Sox: 5 Trades They Could Make with the Rebuilding Chicago Cubs

The Boston Red Sox and the Chicago Cubs' offseasons have been very different, yet still share one similarity—Theo Epstein. 

As many of you know, Epstein was Boston's GM since 2002, leading the Red Sox to two World Series Championships.

The epic collapse during the 2011 season forced many changes throughout the Red Sox organization over the past few months, but none bigger than Epstein's choice to leave Boston and become the president of the Chicago Cubs.

Epstein's first order of business as a member of the Cubs was to name former Padres GM Jed Hoyer as the new general manager. 

Hoyer's name should ring a bell for many Boston fans; he was a huge part of the Red Sox from 2005-09.

When Epstein took a leave of absence in 2005, Hoyer and now current Red Sox GM Ben Cherington, and two other executives, took over the position.

Now Cherington is left to solve Boston's internal issues while Epstein and Hoyer will try to end what has become a 103-year World Series drought.

Fortunately enough, all three still have good relationships with one another and future collaborations involving trades shouldn't be far off. 

The Cubs have started to rebuild their team by trying to eliminate the terrible players and contracts, and getting some good prospects into the organization. 

I have prepared five possible trades that aren't too crazy to be pulled off in the near future.

Starlin Castro for Jose Iglesias and Che-Hsuan Lin

Starlin Castro is one of the great up-and-coming shortstops in the MLB; the Cubs could have something special with him on their team. 

It will be tough for Cherington to pry Castro away from Chicago, but Boston really needs a solid long-term shortstop.

Last season, Castro hit .307/.341/.432 with 91 runs, 36 doubles and 22 stolen bases.  His 207 hits led the National League, making him the youngest player ever to lead the league in hits. 

Castro's defense was very shaky last year, committing 29 errors and producing a .961 fielding percentage, but his skills are expected to improve with experience.

Boston has a young shortstop in Jose Iglesias who looks to be in the mix over the next few seasons, but his offensive struggles are definitely a cause for concern.

His fielding isn't close to an issue as he continues to impress at shortstop, but a .235/.285/.269 hitting line in Triple-A doesn't seem to be improving.

To sweeten the deal, Boston would need to throw in outfielder Che-Hsuan Lin, a player who split his 2011 season between Double-A Portland and Triple-A Pawtucket.

Lin has great potential as a Gold Glove outfielder, primarily playing center field in his career.  He doesn't hit for power and still needs some time in the minors, but could turn into a solid major leaguer.

In this proposed deal, Boston would acquire the shortstop they need while Chicago would get two great defensive players who could be MLB ready within the next year or two. 

Marlon Byrd for Ryan Kalish and Felix Doubront

Ryan Kalish and Ryan Sweeney are really the only true candidates for the Opening Day right field spot as of now, and it doesn't seem like either can hold down the position full-time.

Kalish has battled injuries for a lot of his young career, and Sweeney was just acquired to play a part-time role on the team. 

The need for an everyday right fielder is evident, and the acquisition of Marlon Byrd would fill that void. 

Byrd hit .276/.324/.395 in his second season with the Cubs, but didn't exactly exceed what they were hoping for. 

He is schedule to make $6.5 million next season, the last year on his contract, and could be on the trade block.

Boston's constant injuries and the acquisition of Sweeney gives me the feeling that they still aren't really sold on Kalish as their future in right field.

Cherington already shipped Josh Reddick—who played right field for half of the 2011 season—to Oakland in the deal to acquire Andrew Bailey. 

Would it be crazy to send another outfielder away?  I don't think so.

Obviously, the deal wouldn't work straight-up, so I am throwing Felix Doubront in as well.  Doubront has mainly played in Triple-A Pawtucket during the last few seasons, but has seen some time in Boston.

It's still questionable if he's going to be a starter in the big leagues, or a reliever, but based on what he's done thus far in Boston, it looks as if he's more of a reliever. 

The Cubs already have two lefties in their bullpen, but still could transition Doubront into a full-time starter if they want.

Ryan Dempster for Michael Bowden and Drake Britton

Boston would like to start the season with more depth in their starting rotation than just Daniel Bard and Alfredo Aceves—two pitchers who have been relievers for the majority of their careers.

Enter Ryan Dempster, a veteran of 14 years who could be their answer.

Dempster went 43-27 from 2008-10, but really struggled in 2011 with a losing record and a 4.80 ERA. 

He is scheduled to make $14 million next season, which is a ton for a team that's trying to unload some of their biggest contracts, and especially for a guy who only won 10 games last season.

This may be a red flag for many Red Sox fans since it seems like the same story as John Lackey, but it would be a one-season test run.  If it doesn't work out, the Red Sox can move on.

The two players Boston would give up in this deal would be Michael Bowden and Drake Britton, who have little to no major league experience.

Bowden has appeared in 37 career games over the course of four short stints in the majors.  He could start next season in Boston, but could be used as trade bait if necessary.

Britton had an absolutely terrible 2011 in Single-A Salem, going 1-13 with an ERA of almost 7.00. 

He is supposed to be a top 20 prospect in the Boston organization; hopefully, he can live up to the high expectations.

Britton already had Tommy John surgery, which could be a cause for concern, but he could be in the major league within a few years.

Jeff Samardzija for Bobby Jenks

Bobby Jenks doesn't have the role he expected to have when he came to Boston last offseason. He was injured for a lot of the season and has had several procedures done this season.

The Red Sox will open the season with closer Andrew Bailey in place, and a set of possible setup men with Mark Melancon, Aceves and Bard. 

So where does the former closer fit in?

Jenks is scheduled to make $6 million next season, the last of a two-year deal, and Boston would have to eat some of that salary if a deal was made. 

Chicago's only reliable reliever as of now is closer Carlos Marmol.  Jenks could give them some stability at the back end of the bullpen.

All Boston would need to ask for in return is Jeff Samardzija, a guy who should've realized by now that he should've been a football player. 

Samardzija would help in the sixth and seventh innings when Matt Albers and Franklin Morales will be pitching. 

Last season, Samardzija appeared in 75 games and recorded a sub-3 ERA while racking up nearly 90 strikeouts in 88 innings. 

His $3.25 million team option was declined, but still remains under team control for now. 

I think that this trade would really help both teams in the long run.  Chicago gets more experience in a young bullpen, only having a one-year commitment, while Boston adds more depth to their bullpen. 

Matt Garza for Alex Wilson and Bryce Brentz

Of any of the players currently on the Cubs' payroll, no one has been more a part of trade talks than Matt Garza. 

The former Tampa Bay Ray went 10-10 in 2011, and had a 3.32 ERA in nearly 200 innings of work.

Garza continued to improve his control of the ball and his anger issues, increasing his K/9 rate from 6.6 to nine. 

Garza is the biggest trade chip for Chicago right now; it's almost guaranteed that he starts the season elsewhere. 

Could that place be Boston?

I've already explained Boston's need for a more experienced starting pitcher, and who better to bring in than a guy who spent 2008-10 playing for the rival Rays? 

Obviously, Garza would come at a big price, but Boston still has some valuable prospects who they could use in a deal.

The first is starting pitcher Alex Wilson, who played mainly for Double-A Portland before being called up to Triple-A Pawtucket. 

Wilson had a great 2011 and was named the Red Sox Minor League Pitcher of the Year.

He went 10-4 in 25 combined starts between the two teams, and is a big strikeout pitcher, averaging about eight per nine innings.  He could be major league ready by the middle of the 2012 if all goes well. 

The second prospect is yet another highly ranked outfielder.  Bryce Brentz, just 22 years old, finished his first full season in Single-A Salem, and had no issues facing tougher competition. 

In 75 games, Brentz hit .274/.336/.531 with 19 home runs and 58 RBIs.  He is someone that really should be held onto, but in dire need, he could be used in a trade. 

He was named the 2011 Minor League Hitter of the Year in the Red Sox organization and clearly could be very good when he reaches the majors.

The need for Garza, or a reliable starting pitcher, is evident; Boston really should take it seriously.

They have signed some veterans to minor league deals, but that would really only be for 2012, whereas Garza could be in a Boston uniform for years down the line. 

Overall, would Garza be worth it?