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5 Chicago Cubs Predictions for the 2014 Winter Meetings Action

Jacob KornhauserNov 28, 2014

Coming into the offseason, it seemed like the Cubs were building momentum. They were seemingly connected to every major free agent, and fans were starting to get hyped about what potential stars they could sign. However, the team hasn't made any significant moves yet as the MLB's winter meetings get ready to begin.

Even though they haven't done anything so far, that doesn't mean they're not going to do anything all winter. In fact, expect rumors to heat back up this offseason as soon as the winter meetings begin. Here are five things to look for from the Cubs as they try to become more competitive for 2015 and beyond.

They Will Miss out on Jon Lester

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There's a good chance the disappointment this offseason could continue for the Cubs and their fans. Even though they've reportedly offered Jon Lester a six-year, $135+ million contract, per Tony Andracki of csnchicago.com, he could still decide to go back to the Red Sox (who he's played almost his entire career with).

While the Red Sox have reportedly only offered the ace a six-year deal worth between $110-120 million, he could still decide to return to Boston because that's where he feels comfortable.

He has repeatedly said that he will choose where he's more comfortable, not necessarily whoever offers him the most money. It's also worth noting that his reported offer from the Red Sox came almost two weeks ago, so they could have upped their offer by now.

Even though the Cubs have offered more money than what is known right now, if Lester can get the Red Sox to match their offer (or at least come close), there's a good chance he could return to Boston.

They Will Sign Two Second-Tier Pitchers

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If the Cubs do in fact lose out on Lester in free agency, they may look to improve their rotation by signing two second-tier starters instead of by signing one ace. The first tier of pitching options is represented by Max Scherzer, Lester and James Shields. After them, there are several second-tier options, such as:

  • RHP Ervin Santana
  • LHP Francisco Liriano
  • RHP Brandon McCarthy
  • RHP Kenta Maeda
  • RHP Jake Peavy
  • RHP Justin Masterson
  • LHP Brett Anderson
  • RHP Jason Hammel

Out of these pitchers, the most likely options the team could go after are Maeda, Masterson, Anderson and Hammel. 

The Cubs' interest in Maeda actually goes back to last offseason when they were said to be looking for more international pitching help beyond Masahiro Tanaka, who got a huge contract with the Yankees. The Japanese pitcher has a fastball that runs between 89-94 mph, and he has good command of a two- and four-seam fastball (both of which he throws with regularity).

Masterson could make sense to the Cubs because he's said he's willing to take a one-year contract in order to prove he can return to form. Last season combined between Cleveland and St. Louis, he went 7-9 with a bloated 5.88 ERA.

However, he's shown the ability to be a solid No. 2 starter in the past—he went 14-10 with a 3.45 ERA just one season ago. He fits the mold of the low-risk, high-reward pitchers the Cubs front office has brought in in recent years.

Anderson is simply a pitcher who hasn't been able to stay healthy over the years. In his six-year career, he's only eclipsed 19 starts once. However, when he has pitched, he's shown promise. He's posted an ERA below 3.00 three times in six years, even though those were in seasons with a small sample size. This is exactly the type of pitcher the Cubs love to take a chance on.

They did the exact same thing when they traded for Jake Arrieta, who had never started more than 22 games in a season, and now he's their ace. They can't expect all their low-risk, high-reward acquisitions to pay off, but Anderson (at just 26 years old) is worth the chance at a high reward.

Hammel, who pitched extremely well for the Cubs last season (posting a 2.98 ERA in 17 starts), has said he would be open to a return to Chicago. The Cubs have mutual interest in a reunion in 2015, so he could be back in Cubby blue next season.

If the Cubs are able to add two of the pitchers from this list, their starting rotation will still be significantly better in 2015.

They Will Sign a Veteran Outfielder

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While the Cubs seem to be set long-term in the outfield—with several young prospects developing—they could use a veteran to platoon out there while some of their younger guys develop more. Two options are Jonny Gomes and Michael Morse. 

Gomes makes a little more sense because he draws more walks than Morse. While this may sound like a weird way to separate the two players, the Cubs are a young, free-swinging bunch that could really use someone who can draw walks to lead by example. Last season, Gomes drew more than one walk per 10 plate appearances.

In addition to being a good locker room guy, Gomes could preach his plate approach to the young guys, which could make him even more valuable in the long run.

Morse, on the other hand, is a more talented overall player, but he may not be interested in platooning in the outfield. He has more power upside, as shown by the 36 home runs he hit in Washington in 2011. However, Morse may be a better option for a team that's one piece away from competing than a team that needs a placeholder in the outfield.

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They Will Trade an Infielder

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The Cubs' curious trade that sent pitcher Arodys Vizcaino to the Braves in exchange for infielder Tommy La Stella may point to a bigger plan. Since—on the surface—the trade doesn't make much sense for the Cubs due to their shortage of pitching and surplus of infielders, it may mean they're preparing for a bigger trade.

Nobody knows quite what trades the Cubs could be looking at, but a top infielder (such as Starlin Castro, Javier Baez or Addison Russell) could possibly be on the move this offseason. Any deal involving any of these players would surely be a blockbuster, likely netting the Cubs an ace in return.

While there are no reports of these players being shopped around just yet, the strange trade for La Stella can be looked at as an indicator of a future move.

They Will Sign Jake Arrieta to a Long-Term Extension

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When there's pitching talent available, you go after it. When you already have pitching talent, you make sure you keep it. The one elite pitcher the Cubs currently have on their roster is Jake Arrieta—and it's reasonable to think they will at least discuss a contract extension with their ace.

He has already said he's open to signing a long-term deal with the team (and that he could override his agent Scott Boras' advice). Boras always advises his clients to hit free agency and not negotiate long-term extensions while current deals are active.

Arrieta has outperformed his contract and deserves a raise. The Cubs know that. Signing their current ace to an extension would be a huge move for the Cubs this offseason, even though it hasn't been talked about as much as signing top free agents from other teams.

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