The Winter Meetings Should Bring Answers

As president of baseball operations Theo Epstein, general manager Jed Hoyer, and the rest of the Cubs’ front office make their way to Dallas for the Winter Meetings; many reporters and bloggers alike are piecing together their own versions of the Cubs’ Winter Meetings preview. After all, there is strong chance that the Cubs could be the most active team at the meetings this week. This week should provide a lot of answers for the Cubs and will create a clear timetable for when Epstein and Hoyer expect to have the Cubs in contention.

While the national media types will be focused on Albert Pujols, Prince Fielder, C.J. Wilson, and Mark Buehrle it is likely that Epstein and Hoyer will likely spend most of their time this week trying to complete trades with various teams. If the Cubs do dive into the free agent market once again, it likely will be for a similar signing to that of David DeJesus. One potential new addition to the free agent market, Cuban outfielder Yoenis Cespedes, will likely be declared as an official free agent at some point this week. Note that the Cubs’ brass spent a week in the Dominican Republic to have first hand contact with Cespedes and other international free agents.

While there will likely be more free agent signings down line for the Cubs, the focus this week will be on the trade market. Between Alfonso Soriano, Carlos Zambrano, and Matt Garza possibly being on the Cubs’ trading block to the Cubs’ rumored interest in Colorado Rockies third baseman Ian Stewart and Sand Diego Padres’ third baseman Chase Headley, it is likely that the Cubs will make a trade or two at some point this week.

Matt Garza, coming of going?

Perhaps the biggest starting pitcher on the trade market is Garza. However, there have been some conflicting reports as to the Cubs’ willingness to trade Garza. Epstein told reporters on Thursday that Garza is the type of player that they would want to build the team around. As the case, many local reporters took that comment by Epstein as meaning that the Cubs are not going to trade Garza this winter. That is not the case. There still is a good chance that Garza could be traded this winter with a possible deal being finalized this week.

No matter how one looks at the Garza situation, the Cubs are still going to build around the starting pitcher in some fashion. For instance if the Cubs decide to trade Garza, the package of prospects they receive in return will likely be strong enough for the Cubs’ to build their farm system around. With the Texas Rangers and New York Yankees–two teams that possess top pitching prospects– interested in Garza, the Cubs are in position to acquire a highly touted pitching prospect if they part with Garza in any deal.

It is also important to realize that the Cubs are not going to trade Garza just for the sake of trading the veteran starting pitcher. Garza still has a tremendous amount of value to the Cubs, and would likely become the team’s ace if he remains with the organization for the 2012 season.

Cubs expected to trade for Chase Headley this week?

Even though the San Diego Padres have yet to place Chase Headley on the trading block, Bruce Levine of ESPN Chicago mentioned on his Saturday morning radio show, “Talking Baseball”. that he expects the Cubs to finalize a trade for Headley this week. From every aspect of Headley’s skill-set, the third baseman is perfect long-term fit for the Cubs at the third base position. Headley, who is under team control through the 2014 season, is not going to provide the same power numbers as Aramis Ramirez but will be a better overall hitter and defender than what the Cubs witnessed from Ramirez over recent seasons. Headley,27, is coming off of a 2011 season that saw him produce a .289/.374/.399/.773 clip in 381 at bats.

Given Headley’s promising future, it likely will take a quality package of prospects to lure the third baseman away from the Padres’ organization. It is possible that Epstein could be dangling third base prospect Josh Vitters, whose off-season would not be complete if not linked to the Padres, as part of a proposed package for Headley. While Vitters could project as a first baseman, or even corner outfielder, the current projection for Vitters is third base. If the Cubs acquire Headley, Vitters’ would then be blocked at the third base position.

Don’t forget about Ian Stewart

If, for whatever reason, talks fall through with the Padres, Epstein and the Cubs’ may turn back to the Colorado Rockies and third baseman Ian Stewart. The initial report was that the Cubs and Rockies had been in discussions involving Stewart, and the Rockies requested Blake DeWitt in exchange for Stewart. However, shortly after the original report surfaced, an updated version of the rumor suggested that the Cubs offered DeWitt to the Rockies for Stewart which is when Colorado made a counter-offer of outfielder Tyler Colvin for Stewart.

With the signing of David DeJesus and the eventual arrival of top prospect Brett Jackson, Tyler Colvin appears to be the odd man out in the Cubs’ outfield picture. The Cubs and Rockies have cooled off their discussions about a possible Colvin for Stewart swap, but if the Cubs fail to acquire Headley this week, the two teams may revisit and consequently finalize the trade.

Other Winter Meeting moves to watch

• Since the DeJesus signing there has been an increasing amount of speculation that Alfonso Soriano will be dealt this week at the Winter Meetings. The Cubs have been discussing Soriano with a number of American League teams among them are the Oakland Athletics. The Cubs’ front office is willing to absorb the majority of the remaining $54 million on Soriano’s contract in order to facilitate a trade.
• There has been an interesting amount of trades that involve catchers this off-season, meaning the Cubs could receive inquiries on catcher Geovany Soto. The Pittsburgh Pirates and San Francisco Giants have expressed interest in Soto in the past, and the Pirates likely still have some degree of interest in the Cubs’ catcher.
• Similarly, the interest in closers this winter appears to be at an all-time high. The Cubs have a number of potential closers in the their bullpen–Jeff Samardzija, Chris Carpenter, and Andrew Cashner–which in turn is the reason why current Cubs’ closer Carlos Marmol may be available in the right trade. The Boston Red Sox are seeking a closer, and the Cubs could benefit from picking away from the Red Sox farm system.