Cubs head into meetings with questions

As the Chicago Cubs’ newly installed front office, led by president of baseball operations Theo Epstein and general manager Jed Hoyer, head to this year's winter meetings, here’s a look at some of the team’s most pressing questions.

1. How will the Cubs go about rebuilding the starting rotation?

The Cubs’ rotation is in need of a major upgrade and new direction under soon-to-be-introduced pitching coach Chris Bosio. During the 2011 season, starting pitchers Andrew Cashner and Randy Wells both went down with arm injuries the first week of April. The organization had no viable options to replace them. Epstein is on record as saying he’ll want to know not only who his first five pitchers are but also six through nine. In other words, he wants depth.

Addressing the organization’s lack of pitching depth may come at a high cost, so the team may take a step backward before moving forward. A large number of team’s are likely to enquire about the availability of 28-year-old righty Matt Garza.

Although Ryan Dempster may be the leader of the staff, Garza is the ace of the team’s group because of his stuff. Please ignore his 10 wins in 2011, Garza left seven other starts with a lead but ended up a no-decision. Garza’s 3.32 ERA in 31 starts was significantly better than the staff’s overall ERA 4.43. Garza still managed to throw 197 innings, striking out 197 hitters despite missing three starts with an elbow contusion.

Tampa Rays president Andrew Friedman found out last year that established pitching can get you back a ton of prospects. Garza’s value to teams like the Rangers, Yankees and Red Sox is obvious. He is under contract control for two more seasons. He’ll make between $8.5 and 9 million in 2012 through arbitration.

Ironically for the Cubs, Garza is the one pitcher on the roster who could be a building block. Still, the team can take a giant step toward rebuilding its future by dealing him to the highest bidder. A major league source has already indicated that the Rangers have asked about Garza’s availability.

Looking at the top free agent pitchers, it’s doubtful the Cubs would pay the $120 million free agent lefty C.J. Wilson is seeking. The asking price for 33-year-old Mark Buehrle also appears to be rising. Industry sources believe Buehrle will get at least three years and $40 million on the open market. It appears more likely the Cubs will go after free agents like Aaron Harang, who might come at a more reasonable price.

Will the Cubs shuffle around their bullpen?

The Cubs’ bullpen was a strength last season, as lefty Sean Marshall continued to lead the way. Right-hander Jeff Samardzija and lefty James Russell continued to grow into their bullpen roles. Samardzja has let team officials know that he’d like to get a chance at the rotation this spring. He grew as a pitcher by leaps and bounds in 2011.

It’s possible Samardzija ends up as the team’s closer if the Cubs move Carlos Marmol. Numerous scouts told ESPNChicago.com that Marmol should bounce back in 2012, after blowing 10 of 44 save opportunities this past season. The baseball talent evaluators point to Marmol’s 313 relief appearances since 2008 – a major league high during that span -- as the determining factor for his down 2011 season. If the Cubs look to trade Marmol, Cashner, Samardzija and prospect Chris Carpenter could all be groomed for the closer role.

What type of players will the Cubs add to fill out the roster?

The signing of David DeJesus last week shows that the Cubs will put a premium on versatile, athletic players this offseason. The Cubs will be looking for more left-handed hitting, and Carlos Pena’s return at first base in 2012 is a possibility. Pena was offered salary arbitration by the club and has until Dec. 7 to accept. If he does, he will have a one-year guaranteed deal with the team. Second and third base will also be assessed as the team moves forward. Darwin Barney and D.J. LeMahieu are possibilities at both spots.

That said, the team’s top free agent need may be a versatile third baseman. Sources say that Colorado’s Ian Stewart and San Diego’s Chase Headley could be trade targets for the Cubs over the next week. The Cubs like both players, and Headley played for Jed Hoyer over the past two seasons in San Diego.

Is Soto still in the plans?

Numerous teams may approach the Cubs about the availability of Geovany Soto. He is coming off a disappointing 2011 season in which he struck out 124 times and led all catchers in errors (13), but the Cubs may hesitate to move him with a dearth of suitable replacements available. Soto will make at least $4 million through arbitration. The Pirates and Giants inquired about Soto at last year’s trade deadline, and the Pirates still may have interest. The Cubs have up-and-comers Welington Castillo and Steve Clevenger in their system. Neither, however, appears ready for full-time duty.

Outside of a wild shot at Prince Fielder, whose agent (Scott Boras) is seeking a seven-year deal, and Buehrle or Wilson, the Cubs may decide to spend their time in Dallas looking for trades and adding more players like DeJesus who are versatile and less costly.