Chicago Cubs' Guide to the Free-Agent Pitching Market

Jacob Kornhauser@@KornSportsCorrespondent IIIOctober 20, 2014

Chicago Cubs' Guide to the Free-Agent Pitching Market

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    USA TODAY Sports

    Cubs president Theo Epstein says of the club, "Between this offseason, next year's trade deadline, and next offseason, we will add impact talent from outside the organization." Most of the impact talent he's referring to is going to come in the way of pitching given the fact that the team has a plethora of young hitting talent in the minor leagues or early in their major league careers.

    This offseason and next offseason provide a prime possibility for the Cubs to add top pitching talent, as many aces and No. 2 starters are becoming free agents in the winter. While the club could wait until 2016 to add significant pitching talent, Epstein's statement makes it clear it's going to attempt making a move this year.

    Given the available starting pitchers, here are five pitchers the Cubs could go after this offseason and how the club should go about pursuing them.

Ervin Santana

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    Age: 31

    Throws: Right

    Experience: 10 years

    Santana has proven the ability to pitch at a high level for multiple teams, mostly as a No. 2 quality starter. In six of his 10 seasons, he's won double-digit games, so he's been the model of consistency. He doesn't fit the mold of an ace the Cubs may want, but putting him behind emerging ace Jake Arrieta could make sense. 

    Should the Cubs sign Santana, it would be a strong sign that they prefer to wait until next year to sign an ace. That way, in 2015 they would treat Arrieta as their ace and Santana as their No. 2 guy. Then in 2016, when aces like David Price are on the market, they could make Arrieta a No. 2 starter behind an established ace.

    Suggested contract offer: Two years, $24 million

    Giving Santana two years would make sure that he is the No. 2 starter during his first year and the No. 3 starter in 2016 if the team signs an ace next offseason. Paying the $12 million annual salary would be at market value based on his track record and age.

Brandon McCarthy

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    Age: 31

    Throws: Right

    Experience: Nine years

    McCarthy could be a great under-the-radar move for the Cubs this offseason. Clearly, this wouldn't be the big splash of the offseason, but it would give their rotation much more depth, especially if they add an ace as well. After being dealt to the Yankees last season, he really turned his game on, posting a 2.89 ERA in 14 starts.

    So now the question becomes: Was last year a fluke for McCarthy, or was it a breakout season? Any team willing to sign him this offseason will clearly be saying it believes it was his breakout year. If the Cubs think they have another diamond in the rough in McCarthy, they could decide to take a flier on him. 

    Suggested contract offer: Two years, $14 million

    At this price, the Cubs would let McCarthy know that they realize his value from last season, but that they must see consistency over a two-year period to give him a big payday. Think of it as paying him slightly more than he's currently worth in order to make the deal look like a bargain a year or two down the road.

Max Scherzer

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    Age: 30

    Throws: Right

    Experience: Seven years

    Scherzer is the hottest commodity on the free-agent pitching market this offseason, and he will probably command the highest salary as well. He's the youngest pitcher that teams may sign this offseason, along with Jon Lester, and he also appears to be the most in his prime. The price could repel the Cubs if they don't think he's the ace they want for the future. 

    However, the numbers Scherzer has put up with the Tigers over the last two seasons are staggering. He's won 39 games and pitched 434.2 innings in the last two years while posting respective ERAs of 2.90 and 3.15 in 2013 and 2014. Now those are ace numbers. He's a difference-maker, and the front office could feel as though he could help push them over the top.

    Suggested contract offer: Five years, $140 million

    Scherzer is set for a huge contract this offseason, and if the Cubs are going to land him, this might be in the neighborhood of what they'll have to offer. This doesn't necessarily mean the Cubs should go after him, but if they do, this is the price they may have to pay. It's for this reason they may favor either of the other two aces on the market.

James Shields

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    Age: 32

    Throws: Right

    Experience: Nine years

    Shields is known for his success in big games and for being a workhorse. Those are two qualities the Cubs know they're going to need in their ace of the future. Even though Shields is older than some other options, he could also be slightly cheaper than the other two aces on the market. 

    The real question the Cubs have to ask themselves is whether they think Shields can sustain success over the next three to four seasons. That should be the early window for contention of this current team. If they think he still has four years left in the tank, it would make a lot of sense for the team to try to lock him up and make him their ace alongside Arrieta.

    Suggested contract offer: Four years, $84 million

    The contract offer could be interesting because Shields could either sign before Scherzer and Lester and set the market for them, or he could wait until they're both signed in order to let the market set his price. Either way, he could command more than $20 million annually. If the Cubs miss out on Lester, they could consider making this type of offer.

Jon Lester

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    Age: 30

    Throws: Left

    Experience: Nine years

    Lester certainly appears to be the Cubs' top free-agent target this offseason based on the fact that he has ties to the Cubs' front office from his time in Boston. In fact, it's very possible that if the Cubs don't end up landing Lester, they won't pursue another ace until next offseason. That specific strategy remains to be seen. 

    For several reasons, though, Lester should be the Cubs' top priority. At the age of 30, he should have three to four more years of prime left barring injury. He's pitched his entire career in the American League, so moving to the National League could make his numbers look even better. You can bet the Cubs front office will make a strong pitch to Lester so they can try to accelerate their rebuilding clock.

    Suggested contract offer: Six years, $156 million

    Giving Lester a sixth year could seal the deal in this case. Also, paying him $26 million a year would almost be an offer he couldn't refuse. All the Cubs have to hope is that a team like the Yankees doesn't drive up the price even further. They might be able to get away with a deal for slightly less than this, but the Cubs could decide that Lester is the pitcher they want to build their rotation around.


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