MLB Free Agency Predictions: Chicago Cubs Poised To Strike

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Sep 30, 2014; Kansas City, MO, USA; Oakland Athletics starting pitcher Jon Lester (31) delivers a pitch in the first inning against the Kansas City Royals during the 2014 American League Wild Card playoff baseball game at Kauffman Stadium. The Royals won 9-8. Mandatory Credit: Denny Medley-USA TODAY Sports

With the MLB Free Agency period beginning on November 8, now is generally the time when predictions are made on where the top free agents will sign. MLB Trade Rumors annually predicts where the top 50 MLB free agents will sign, and given their craft, their predictions are fun to ponder. In their predictions for the 2014 class of MLB free agents, MLB Trade Rumors has the Chicago Cubs cleaning house. 

The Chicago Cubs are expected to be active when the MLB Free Agency period begins on November 8. With Joe Maddon in place as manager and a commitment towards winning the National League Central title in 2015, the Cubs are expected to be a desirable destination for many of the top free agents this winter.

MLB Trade Rumors annually predicts where the top 50 MLB free agents will sign. In their predictions for the 2014 class, MLB Trade rumors has the Cubs cleaning house by signing starting pitchers Jon Lester, Jake Peavy, and Justin Masterson; catcher Russell Martin; and relief pitcher David Robertson.

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  • For Lester, MLB Trade Rumors banks on the notion that the Cubs are the industry favorites to sign Lester.

    "Jon Lester – Cubs. Lester, a 30-year-old southpaw, posted a 2.46 ERA this year in 219 2/3 innings for the Red Sox and Athletics. He was actually better this year than Scherzer in terms of ERA, and the two share identical 3.58 career marks. Owing to a midseason trade to Oakland, Lester is ineligible for a qualifying offer. Unable to work out an extension with Lester, the Red Sox traded him, but both sides have made an offseason reunion sound more likely than it usually is when a pending free agent star is dealt. However, the Cubs are viewed as the industry favorite for Lester, given Theo Epstein’s time in Boston, the Cubs’ need for frontline starting pitching, and their large spending capacity this winter. Lester should command at least the six years and $147MM Greinke received two years ago, and potentially more."

    Lester would be a perfect for the Cubs. If the Cubs do have aspirations of contending in 2015, then the team is going to need a starting pitcher that can carry them. Lester is that that pitcher.

    For Martin, MLB Trade Rumors believe that he is an upgrade over Welington Castillo.

    "As the only catcher on this list and possibly the only viable free agent starting option at the position, Martin is in the catbird seat. A career-best .402 on-base percentage further bolsters his case, and he’s known as an excellent defender and handler of pitching staffs. The Pirates will make a qualifying offer and extend their budget to try to re-sign him, but he’d make a fine upgrade over Welington Castillo for the Cubs. The Dodgers could also get involved, and Martin would be an upgrade for the White Sox, Rockies, Tigers, Astros, and Mariners as well."

    Castillo is in an interesting position with the Cubs. Much has been made about the core of young players on the Cubs, however, Castillo is hardly mentioned as part of that core. For a team looking to contend, having the veteran leadership of Martin may be the biggest piece to the puzzle in 2015.

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    With Robertson, MLB Trade Rumors believes that Cubs are the team to give the reliever a big payday.

    "Robertson is the best free agent reliever this winter, and the 29-year-old may be aiming to top Jonathan Papelbon’s four-year, $50MM deal. Indeed, a reliever of Robertson’s caliber hasn’t hit the free agent market since Papelbon three years ago. The Yankees will tender a one-year, $15.3MM qualifying offer, which Robertson should easily turn down in search of a career payday. The Cubs and White Sox are other potential fits given large amounts of payroll space and protected first-round picks."

    Robertson had big shoes to fill in New York after replacing the retired Mariano Rivera. After notching 39 saves last season and having an ERA of 3.08 with a FIP of 2.68, Robertson is going to receive a payday. Though, the Cubs appear to be pleased with Hector Rondon, Neil Ramirez, and Pedro Strop as their late-inning relievers.

    The Cubs have developed a reputation of taking a chance on starting pitchers looking to bounce back from a poor season and that is why MLB Trade Rumors predicts that Masterson will sign with the Cubs.

    "Masterson, 30 in March, was very good in 2011 and ’13 when he was able to keep his walk rate in check.  The lanky righty has a bowling ball sinker and the groundball rate to back it up.  The Indians were unable to lock him up long-term, trading him to the Cardinals on July 30th.  Masterson struggled with both teams, but knee inflammation was a mitigating factor.  The Cubs are a good fit given the Theo Epstein connection and Masterson’s Midwest upbringing, but it’s likely a dozen teams will show interest in the pitcher.  There’s a good chance he gets multiyear offers, but he may prefer one year to rebuild value."

    Masterson had a 5.88 ERA in 2014 with a FIP of 4.50. Furthermore, after being traded to the National League, Masterson had a -0.5 WAR. Masterson has a career era of 4.24 and could be a nice reclamation project for Cubs’ pitching coach Chris Bosio.

    Jake Peavy has stopped short of saying he will be signing with Cubs while speaking with reporters during the post-season but where there is smoke, there is fire and that is why MLB Trade Rumors has Peavy signing with the Cubs.

    "Peavy enters free agency for the first time in his career, and the 2007 Cy Young winner is now a mid-rotation starter.  He posted a 3.73 ERA for the Red Sox and Giants this year.  His stock improved given a 2.17 ERA in San Francisco, even if he won’t be able to repeat the 3.2% home run per flyball rate he experienced there.  His agent may seek a three-year deal, but two seems more likely.  Peavy seems likely to weigh factors other than money heavily in his decision.  He likes the idea of a free agent package deal with buddy Jon Lester, though the Cubs aren’t likely to sign all three pitchers for which they’re listed here.  There should be plenty of suitors for Peavy, but his personal preference will play a big role."

    Peavy would be a solid option for the Cubs at the back end of their rotation but nothing more. Peavy enjoyed his time in Chicago with the White Sox and that could be what leads him to returning to the city and signing with the Cubs.

    The Cubs are entering exciting times. That much will be clear when the Cubs’ introduce Joe Maddon as their manager on Monday.