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2014 MLB Winter Meetings Preview

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A look at this week's Winter Meetings with an eye on the possibilities for the Cubs

San Diego, where the Winter Meetings begin on Monday
San Diego, where the Winter Meetings begin on Monday
George Rose/Getty Images

The Winter Meetings used to be the baseball offseason's best real opportunity to make deals and sign free agents. The entire Major League Baseball establishment convened in one spot for five days. Deals were made, franchises were reshaped, and the dream of building a contender in a week could come to fruition... if you transacted wisely.

In the Information Age, sticking the front offices of all 30 teams in one building is far less important. Deals are discussed and completed over the phone; I suspect that text messages and video calls have entered the fray as well.

Nevertheless, the Winter Meetings remain the offseason's marquee event and the biggest deals of the winter still tend to go down this week. From the past five Winter Meetings, here are some of the highlights to whet your appetite:

2009
The Yankees, Tigers, and Diamondbacks pulled off a blockbuster involving Ian Kennedy, Edwin Jackson, Curtis Granderson, Austin Jackson, and Max Scherzer.

2010
The Red Sox sign Carl Crawford.

2011
The Angels signed Albert Pujols and C.J. Wilson. The Marlins sign Jose Reyes and Mark Buehrle.

2012
The Red Sox signed Mike Napoli and Shane Victorino.

2013
Nothing really significant happened as Jacoby Ellsbury, Brian McCann  and Robinson Cano all signed the week before the Winter Meetings.

The point of the above snippet: lots of moves always happen at the Meetings, and oftentimes the biggest names make their moves this week. We certainly shouldn't expect to see every player find a home, but we should expect to hear lots of rumblings.

Many of them will be agents and front offices floating falsities. Some of them will be genuine discussions that don't lead to anything substantive. Yet some of them will be the genuine laying of groundwork for a move to come. The 2012 Meetings are instructive in this regard: although none of the winter's biggest names made their move at the Meetings, the Dodgers, Angels, and Tigers laid the groundwork for their marquee offseason signings that occurred within the following two weeks: Zack Greinke, Josh Hamilton and Anibal Sanchez, respectively.

Much of what happens will occur outside of the public eye. Despite that, there will be a ton of noise that we get to hear about.

With all of that said, here is a look at the biggest storylines for the Cubs at the Winter Meetings followed by a snapshot of what figures to dominate the discussion in the baseball world at large.

Lester, Lester, and More Lester
It's no secret: most folks with far more access to players and front offices than any of us will ever have expect Jon Lester to find a home in the coming days. Regardless of where he lands, Lester's choice should help some other dominoes fall. Lester certainly appears to be holding the keys to the Cubs' offseason. At the very least, his decision should enable the club to move forward, regardless of whether he causes us to jump for joy or breaks our hearts.

Are There Any Bats Left Worth Buying?
In short: yes. But barely.

As has happened in previous offseasons, many of the premier offensive players in the game found new homes in November and/or prior to the Meetings: Hanley Ramirez, Russell Martin, Pablo Sandoval, Nelson Cruz, Victor Martinez, Nick Markakis, Aramis Ramirez, and Adam LaRoche have all found their homes for 2015. Of the top remaining position players, most of them derive much of their value from their defensive work, including Chase Headley, Asdrubal Cabrera, Nori Aoki, Colby Rasmus, and Emilio Bonifacio. Only Melky Cabrera and Michael Morse figure to offer the ability to be a impact additions with their bats.

Given the relative dearth of established offense, expect the Cubs to pursue at least one of the following:

A Free Agent with an Impact Glove
Perhaps the Cubs like the idea of going after Headley's vacuum at third base, an idea whose merits we discussed on Friday. Perhaps the front office loves the idea of Aoki's glove and speed in left field. Maybe Bonifacio's all around glove work will be enough to justify a return. The Cubs will likely look to free agency's middle class in search of a solid statesman to add to the young core.

Either that, or...

A Veteran Bat with Some Control
The Cubs' collection of young, high-ceiling bats is well known. The 2015 lineup figures to feature Anthony Rizzo, Javier Baez, Starlin Castro, Kris Bryant, Arismendy Alcantara, and Jorge Soler. That leaves Welington Castillo fighting for the catching job and another spot -- likely either third base or an outfield spot -- available for upgrade, provided that the sextet listed above stays in the organization.

While I'd be a bit surprised to see the club move any of its more valuable chips for a one-year rental, there are plenty of established bats with more than one year of control remaining. Should the Brewers decide that its time to rework their organization, Jonathan Lucroy and Carlos Gomez would both be extremely attractive to the Cubs. Should the Rays target 2016-17 as their next competition year, Ben Zobrist could be moved. Perhaps Jon Daniels and the Rangers would like to shed the remaining $34 million owed to Adrian Beltre over the next two years. Maybe the Phillies would be something rational like... okay, just kidding. There are plenty of options for a trade target.

Other Possibilities
I get the sense that just about every possibility is on the table for this front office. While the Cubs would likely need something like Andrew McCutchen and Starling Marte to actually move Anthony Rizzo, meaning Rizzo isn't really available, I don't think anyone is categorically off limits. That's good.

The Cubs could consider dealing from some of their back-end starting pitching surplus, particular those without the ability to be optioned to Triple-A. That group includes Felix Doubront, Jacob Turner, and Travis Wood; though Tsuyoshi Wada also can't be optioned without having to clear waivers, I believe he cannot be dealt until June.

Management will certainly listen to possibilities regarding Edwin Jackson, though if Edwin is dealt I suspect that it will be much later in the offseason. According to CBS Sports, only two of the top 25 pitching free agents have signed as of yet. Teams figure to hammer the free agent market prior to making any notable deals for reclamation projects like Edwin.

Finally, many of us suspect that a Dan Vogelbach trade is coming, whether soon or in the next year. It would hardly be surprising if the Cubs found an appealing deal with Big Dan as a key piece, likely with a power-strapped American League team like the Rays, Royals, or Mariners, teams with a dearth of power both currently and in their systems.

Other Things to Watch Around Baseball
Though we've focused on the Cubs so far, the other 29 teams all get to play this week too! Here are some quick hits to watch for:

  • Will the Braves find a buyer for Justin Upton or Evan Gattis (or both)?
  • Will Lester's probable signing cause an avalanche of starting pitching signings, save for Max Scherzer?
  • Will the A's continue to alternate win-now moves with rebuilding trades, confounding the baseball world?
  • Will the Mets finally decide to make a move that genuinely improves their offense after a series of band-aids has left them wanting much more?
  • And for me, the most interesting thing to watch: will the Reds go for broke in 2015 or throw in the towel with their entire non-Homer Bailey starting staff heading for free agency next winter?

There are certainly countless moves that could happen: the Twins could look to sell-high on Phil Hughes, Mike Ilitch could make his annual spending splurge to augment his team's aging core in Detroit, and the Blue Jays could look for a second baseman to complete their lineup overhaul. This is the peak of the silly season where we'll hear lots of fabrications (like this paragraph so far) and get some actual big moves.

It's time to dig in and enjoy the ride!