The 2013 season for the Cubs was about what you'd expect: a lot of losses, some hope for the future, and a decent bit of frustration. With Chicago's farm system taking another step forward, 2014 should provide more hope, less frustration, and probably about the same amount of losses, even with an unnamed new manager in tow.
Needs
The Cubs successfully discharged nearly every free agent they had during the season. The only players they'll lose are closer Kevin Gregg, starter Scott Baker, and catcher Dioner Navarro. Really, that's it. None of those three were even a crucial part of the squad, as Navarro was the team's second catcher behind Wellington Castillo and Baker made just three starts for the club, while Gregg struggled in the second half to kill his trade value.
But just because the Cubs aren't losing anyone doesn't mean that they're going to ignore the free agent market. Chicago could use a veteran backup to help ease the load off of Castillo following September knee surgery. The could maybe look at a starting pitcher or two as well, especially if they end up trading Jeff Samardzija. I think they could also look for an outfielder as well, much like they did last winter when they signed (and hit with) Ryan Sweeney and Nate Schierholtz, but they wouldn't be in the hunt for a player like Shin-Soo Choo or Nelson Cruz. Third base is another area where the Cubs could look for a temporary upgrade, but simply giving the job to Mike Olt is probably the best course of action.
Possible Options
It's all about buying low. Last winter, the Cubs were busy, but their biggest signing was starter Edwin Jackson. This winter, I wouldn't really expect the team to bring in a guy like that. More signings of the Baker/Feldman/Sweeney/Schierholtz/Hairston mold would make sense for the Cubs. Feldman got them a nice package from the Orioles last summer, and Hairston got them a decent enough return from the Nationals. If you want to look at starting pitchers that could interest the Cubs, Gavin Floyd seems like an ideal fit as a guy returning from Tommy John who already played in town with the White Sox. Former Ranger Colby Lewis could also draw some interest. As for position players that may wet the club's whistle, there are not a lot of players out there right now that make much sense. Maybe someone like a Roger Bernadina could work out for them as a fourth outfielder, but I think if the Cubs make a move, they'll wait to see which players are nontendered.
Trade Options
Now this is where things can get interesting. Starlin Castro is the team's franchise shortstop and locked up long-term, but his disappointing 2013 could push the club to at least explore a deal for the erratic 23-year old, especially considering the free agent market at shortstop could best be described as "Stephen Drew and fifty feet of crap". The Cubs could also look to trade starting pitcher Jeff Samardzija after the 28-year old regressed in his second year as a starter in the majors. He still has two years of arbitration left, and the Cubs don't want to hold on to him too long like they arguably did with Matt Garza.
Trade Targets
Young talent, of course. But because of how strong their farm system already is, the Cubs definitely have the goods to trade for any player that is put on the trade market. If the Cubs wanted to blow everything up and acquire a legitimate ace in David Price, they could top nearly any package offered to the Rays. If they wanted to pry Giancarlo Stanton from the Marlins, they could make the two packages they sent to Miami for Matt Clement and Juan Pierre (which included Dontrelle Willis and Ricky Nolasco, respectively) look like chump change. Chicago's in a solid position this winter – they're not pressured to win, so the front office doesn't need to make rash decisions. Furthermore, they have the resources to make waves if they so desire, putting them in a rather enviable place.
