The Red Sox are in first place in a tough American League East, but they don't have a lot of breathing room. Going into last night, there were four teams within six games in the AL East, so this division is likely to go down to the end. With the best record in the AL right now, they're in good shape, but they're only two games from being outside of the playoffs entirely.
Needs (likelihood to deal for position in italics)
Starting pitching-High: Clay Buchholz and John Lackey have been good (although Lackey's peripherals suggest a correction) and Felix Doubront, Jon Lester and Ryan Dempster have been OK. Buchholz is hurt, but is expected back soon. By that time, hopefully he's learned how to spell his name correctly (2 Hs? What a weirdo). The Red Sox could really use a top of the rotation starter to solidify their starting pitching.
Closer-High: The Red Sox bullpen has been OK, but their closer spot has been a problem for them. The Red Sox recently removed Andrew Bailey from that role and are going to hand the closer keys to Koji Uehara. If Uehara struggles, it seems very likely they'll go shopping for help here.
Right Field-Low: Shane Victorino has been really bad offensively, but he plays good defense and they just gave him a huge contract, so it's robably a spot they leave alone.
Shortstop-Medium: Stephen Drew has been doing what Stephen Drew does -- play solid defense and do nothing offensively. At this position, maybe that's OK, but I'm sure they'd like to get a little more offensively at shortstop.
Third Base-Medium: Red Sox are in a pickle here, as Will Middlebrooks was a stud prospect that has been 5 shades of awful so far this year. The Sox could call up Xander Bogaerts to see if he can handle third base, but that feels to me like it'd be rushing him a bit.
Fits on the Cub Roster
The Cubs have Matt Garza and Scott Feldman as starters that could interest the Red Sox. Kevin Gregg could be a closer option for the Red Sox if they're trying to fill that spot cheaply. Luis Valbuena is the kind of OBP, solid defense guy that the Red Sox could use at third base. Heck, even Cody Ransom could make sense if the Red Sox just want insurance in case Middlebrooks continues to struggle.
What's in it for the Cubs?
Ranked the 16th- and sixth-best organization for talent by Baseball Prospectus and Baseball America, respectively, clearly this farm system has some disagreements about its quality. There's quite a lot of top end talent here, though. Everyone loves Xander Bogaerts and for the rentals that the Cubs are offering, he's probably off the table. Same goes for Jackie Bradley Jr., who has been great at Triple-A this year and is a Top-25 prospect in baseball.
Where it gets interesting is the next tier of guys and they're interesting because they fit the Cubs need: starting pitching. Matt Barnes led the group this offseason, but he's struggled quite a bit in Double-A at age 23. He is still striking a ton of guys out (10.9K/9IP) but teams are also getting a ton of hits off him (10.1H/9IP). The next guy in the pecking order is one we heard about quite often in the Ryan Dempster trade talks last year and that's Allen Webster. Webster is a consensus top 100 prospect that has been pitching well in Triple-A. If you're looking for a guy that can step into the Cubs rotation next year, he's your guy.
Henry Owens came into the year as a fringe Top-100 pitching prospect and he's been dominating High-A this year. He's got 80Ks in 65 innings this year while posting a 3.03 ERA. The wild card in this system seems to be Anthony Ranaudo. A consensus top 100 prospect 2 years ago, he posted a 6.69 ERA last year in Double-A. This year it's been a completely different story, with Ranaudo sitting at a 2.34 ERA in Double-A with 82 strikeouts in 73 innings. Garin Cecchini is the last guy I'll mention and that's because he came into the year as a highly sought after third base prospect that's boosted his stock by showing more power and a better hit tool. He's OPSing over 1.000 in high-A and is known for having a great eye.
Boy, after going through all those guys, it's tough to imagine the Red Sox being anything but a Top-10 system. Maybe they lack depth? The links above can tell you more about what they have in their system.
Overall Fit- High
The Red Sox system and needs seem like a great match for the Cubs and I'm sure the hope is that they can deal Garza for a package including one of those pitching prospects listed above.
Next Up: The Baltimore Orioles