Winter Meetings Preview: What the Cubs Are Looking to Do

The World Series champion Chicago Cubs are back at work trying to shore up a roster that won 103 games and a title last season, and this week's Winter Meetings in Washington D.C. are critical as the team looks to set themselves up for a repeat

When your team wins a World Series championship, you’re required to get back to work very quickly to defend that title, and that’s what’s happening for the Chicago Cubs as they prepare for baseball’s annual Winter Meetings this week.

The Cubs, who won their championship a little over one month ago, have made big splashes at the meetings before, including landing Jon Lester in 2014, and while it’s unlikely that they’re going to make a giant splash in the free agent pool this time around, they could still make moves to improve an already loaded roster.

With that in mind, here are three things that the team is likely to be looking for as they set up camp in the nation’s capital this week.  

Bullpen Arms, Including a Closer

The Cubs are very confident in guys like Carl Edwards Jr. to be among their future weapons in the bullpen, and they already have a solid 1-2 punch at the back end with Pedro Strop and Hector Rondon both being capable of handling those important jobs.

The big question for the Cubs is whether or not they trust Rondon to remain healthy, as he dealt with injuries through a large chunk of last season. If they don’t, then there are several available options, and although it seems like a long shot that they could get involved on a free agent like Aroldis Chapman or Kenley Jansen, the trade market may be a more likely option for the team.

Two names to look out for in that department are Wade Davis of the Kansas City Royals, who are going to be looking to unload at least one or two high-profile players this offseason, and David Robertson of the Chicago White Sox, who has a big contract and could be someone the team is looking to jettison if they’re serious about starting a rebuilding process.

Young, Cost-Controlled Starter

For years now the Cubs have said over and over again that they want to parlay some of the tremendous assets in their farm system into a young, cost-controlled starting pitcher, and this could be the offseason that we finally see them do that.

While players like Chris Sale and Jose Quintana are likely off the radar for the Cubs given their insanely high price tags, there are still other options that the Cubs could pursue. Arguably the biggest fish they could land is Tampa Bay Rays star Chris Archer, but that would definitely require the Cubs giving up high-profile prospects like Eloy Jimenez and could even mean an MLB talent like Javier Baez or Jorge Soler would have to be included.

If a player like Archer proves to be too expensive, there are other options as well. A trade could still work, with Rays pitcher Drew Smyly a possibility, and the Cubs could also make a run at acquiring Shelby Miller from the Arizona Diamondbacks. Miller, who had a horrendous 2016 season, would certainly come cheap, but with his reputation for restoring confidence and effectiveness to pitchers, Chris Bosio could do well with that challenge.

One other potential option could be a contract for Tyson Ross, a young pitcher previously linked to the Cubs in trade rumors that was recently non-tendered by the San Diego Padres. He is recovering from a very serious injury, but that could work in the Cubs’ favor if they want to sign him to an inexpensive contract.


With the retirement of David Ross, there is a possibility that the Cubs may want to add another veteran catcher to the mix. The team already has Willson Contreras and Miguel Montero in the fold, but with how successful they were in carrying three catchers last season (and with the small possibility that Montero could be traded after his public airing of grievances after the season ended), there are a few options worth considering on the open market.

One such possibility would be a reunion with Welington Castillo, who was recently non-tendered by the Diamondbacks. The catcher has shown some solid power potential and is a solid pitch framer, and he could be an intriguing option should the Cubs want to get their feet wet in the catching market.

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