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A Response And A Counter-Proposal: This Offseason, Theo Epstein and Jed Hoyer Should...

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Recently, Al threw out his personal proposal for the front office this winter. He made six specific proposals. I started responding in the comments, but as so often happens, my reply ballooned into something much larger.

Who will Theo & Jed add to the Cubs' roster for 2015?
Who will Theo & Jed add to the Cubs' roster for 2015?
Getty Images (Photo Illustration: Mike Bojanowski)

In the spirit of healthy debate, I'm going to offer my own analysis of Al's six proposals and follow with my own ideal offseason, at least as it stands now.

1. Sign Jon Lester. Al gets a 100 precent endorsement on this one. I'm pegging his contract at a 6-year, $154 million pact. This contract effectively represents the CC Sabathia deal at $2 million more per year; Sabathia also signed in advance of his age-31 season. Perhaps the Cubs will be able to make that sixth year a vesting option based on injury as the Yankees did.

2. Sign Justin Masterson. To me, Masterson depends entirely on the contract. Al suggested a one-year deal with an option, a low base salary, and plenty of incentives. If Masterson takes that deal, I'm all for it. Masterson was all kinds of terrible in the second half this year after a mediocre first half, but that came on the heels of five average or better years. I'm concerned that his slider velocity dropped precipitously; as a two-pitch starter, Masterson desperately needs both offerings. Unless he's taking something in the range of $2 million or less plus incentives, I'm going to pass and allocate this money to a safer commodity.

3. Eat Edwin Jackson's contract and release him. Our first major divergence! Look, Edwin was brutal in 2014. That's a fact. Yet even though this is much easier to say months removed from his last dreadful start, I don't understand the rationale for simply punting on him. A bad contract swap would be fine. Barring that, I'd hold Edwin as a long man/spot starter for three reasons: (1) he's still only 31, (2) his FIP was between 3.55 and 3.86 each year from 2010-13, and (3) by all accounts he's a good dude who works hard and sets a good example. It's not as if Edwin has never been good, so it's not unreasonable to think that he might provide some modicum of value again. He's not exactly blocking anyone's access to the long man role. I just don't feel a sense of urgency to kick him aside just yet.

4. Sign one of these free agent lefthanded relievers: Neal Cotts, Andrew Miller, or Zach Duke. Please don't. Don't spend big on relievers, especially lefties. Cotts signed minor league deals for the 2010, 2011, 2012, and 2013 seasons. Miller was non-tendered before the 2011 season. Duke signed minor league deals before the 2012, 2013, and 2014 seasons. Find some of those guys instead, the minor league guys trying to hang on. Throw four guys at the wall and see who sticks as a LOOGY. Or just trust that Wesley Wright can do the job again. The four largest lefty reliever contracts from last winter went to Boone Logan (3 years, $16.5 million), J.P. Howell (2 years, $11.25 million), Javier Lopez (3 years, $13 million), and Eric O'Flaherty (2 years, $7 million). Those deals netted a combined WAR of -0.6 with only Howell posting a positive figure at 0.3.

5. Look into signing Nick Markakis. For me, Markakis is akin to Mike Morse, Hanley Ramirez, Aramis Ramirez, Nori Aoki, Nelson Cruz, and Alex Rios: they're all guys who are plenty good for everyday jobs who shouldn't have everyday jobs on our team. Markakis gets on base well, hits for no power, and is an absolute butcher in an outfield corner. That's Chris Coghlan from 2014 except that Coghlan hit for some power and his defense stabilized a bit. We don't need to pay those guys; we should pay for elite talent and let the system fill in around the stars.

6. Take a flyer on one of these two outfielders: Mike Carp or Colby Rasmus. Absolutely -- flyers are great! Spending the minimum to see if a talented player puts something together for you is always worth it. With Rasmus, find out if the attitude matches the reputation. With Carp, see if the power is still strong. If not, no big deal.

As so often happens with reasonable people, Al and I agree on some of these points while we disagree on others. With that said, here's what I'd do and why:

1. Sign Jon Lester to a 6-year, $154 million contract. See above.

2. Sign Russell Martin to a 4-year, $48 million contract. I really like Martin and think that he's a tremendous fit for our ballclub. I also recognize that his market will likely come in higher than this figure. Realistically, he's a guy with average power, great walking ability, and a stellar defensive profile...who just hit over .250 for the first time since 2008. If he's back to .230/.320/.360 next year, I'm not too excited about paying even this much, let alone any more. He's 32 in 2015. If his market settles above this point, roll with Welington Castillo and reallocate the cash elsewhere.

As for the second-round pick that the Cubs would have to surrender, it is almost quite literally the worst draft pick a team can surrender for acquiring their first compensation free agent. Had we won a few more games, we're talking about the 11th pick or the 12th pick; instead, we're talking about a pick in the mid-40s, twenty slots worse than the pick playoff teams would surrender. Those picks have value, but it's not nearly as high and the value of a productive everyday catcher to our club over the next few years is massive, particularly one with on-base skills in our powerful lineup.

3. Keep Edwin Jackson. See above.

4. Go hard after Chase Headley. I know what you're thinking: Kris Bryant, Luis Valbuena, Javier Baez, Addison Russell, and even Christian Villanueva and Jeimer Candelario. Third base is the Cubs' deepest position. I agree.

Here's the counter: Headley is a fringe star who appears likely to get Edwin Jackson money. If Headley can be had for something like 4 years, $56 million, the Cubs should be all over him. If he wants a shorter deal, great! He's the best third base glove in the game outside of really-a-shortstop Manny Machado. If he brings anything with the bat, he's an undeniable star. Here's the thing about Headley's bat: the general consensus is that the bat is underwhelming or even poor. Here are Headley's home/road splits for his career, slightly tainted by a late-season run in Yankee Stadium this year:

Home: .245/.335/.376
Road: .285/.359/.440

Top-two defensive third baseman plus a bit better for his career than Luis Valbuena's career year on offense equals a stud. Some team is about to reap tens of millions of dollars of surplus value on Headley simply by removing him from Petco Park; I'd like that team to be the Cubs.

It also doesn't complicate roster construction in the shorter term. Arismendy Alcantara stays in center field, Jorge Soler stays in right field, Anthony Rizzo stays at first base, Javier Baez stays at second base, and Starlin Castro stays at shortstop. Kris Bryant kicks to left field, Headley mans third base, and Valbuena becomes either a great substitute or an important complementary piece in a trade. Coghlan and Justin Ruggiano give tremendous outfield depth. Who doesn't like the sound of that roster, one that legitimately pushes three everyday-caliber players to the bench?

5. Sign Chad Billingsley to a one-year contract with an option. Billingsley's arm and shoulder are messed up. But when healthy, he was a very strong starter. How about a reverse Josh Johnson deal where Billingsley gets a $4 million salary in 2015 for, hopefully, something like 10 starts with the Cubs securing a $7 million option in 2016? I like that use of our financial strength and flexibility. If he requires a 40-man roster spot, I'll pass.

6. Sign either James Shields or Brandon McCarthy. This depends on what happens with Russell Martin. If the Cubs nab Martin, it's Martin and McCarthy. If not, it's Castillo and Shields. Either option is strong.

Shields is old, something that is a bit of a bummer. A 4-year, $88 million deal would cover his ages 33-36 seasons. Yikes. On the bright side, Shields has been remarkably consistent for eight straight years with his 30s looking just as strong as his 20s. More importantly, his fastball usage hovers around an incredibly low 40 percent and the pitch's velocity has actually upticked slightly over the last five years. He uses his cutter, curveball, and changeup all about 20 percent of the time each, and those pitch velocities have held consistent. Shields is no Ubaldo Jimenez, he of alarming swings in velocity and effectiveness. Shields is steady.

As for McCarthy, his trade to the Yankees was unfortunate for his pursuers. The massive gap between his ERA and his FIP closed substantially after his move to the Bronx. Over a few months, he morphed from a great buy-low target into another guy expected to earn well on the market. He comes with significant injury risks: this year was his first year with either 200 innings pitched or 30-plus starts as a professional. Even with all that, his pedigree suggests that he'll nab something in the three-year, $30 million range.

So What Does It All Mean?
If the Cubs follow the above plan (assuming Martin signs elsewhere and the Cubs tab Shields instead of McCarthy), the following club would be in place by late April:

3B Chase Headley
SS Starlin Castro
1B Anthony Rizzo
LF Kris Bryant
RF Jorge Soler
2B Javier Baez
CF Arismendy Alcantara
C   Welington Castillo

Bench: INF Luis Valbuena, INF Mike Olt/Logan Watkins, OF Chris Coghlan, OF Justin Ruggiano, C Rafael Lopez

SP1 Jon Lester
SP2 Jake Arrieta
SP3 James Shields
SP4 Kyle Hendricks
SP5 Felix Doubront/Jacob Turner/Travis Wood/Dan Straily/Dallas Beeler

Bullpen: Hector RondonNeil Ramirez, Pedro Strop, Justin Grimm, Wesley Wright, Brian Schlitter, Edwin Jackson

Is that something you might be interested in?

You can play with the bullpen with the likes of Arodys Vizcaino, Armando Rivero, Blake Parker, and Zac Rosscup all fighting for innings. The team also has the luxury of going with a big bat (with no glove) on the bench thanks to the presence of Castro, Baez, and Alcantara; no need for an additional backup shortstop there.

The cost breakdown of the above 25-man roster (assumes a minimum salary of $515,000 -- this figure is yet to be calculated under the Collective Bargaining Agreement but will be $500,000 plus a cost of living adjustment):

Starting Lineup: $30.645 million
Bench: $8.03 million
Starting Rotation: $53.582 million (giving #5 job to Doubront)
Bullpen: $17.475 million
TOTAL: $109.732 million

Such a payroll would have ranked 15th in 2014, just less than Arizona, Cincinnati, St. Louis, and Atlanta, and just a bit more than Baltimore and Milwaukee.

This is easily, far and away, my favorite fake team that I've built for 2015. It requires three big forays into the free agent market for players in their 30s, so consider me skeptical that the front office might actually pull it off. Regardless, it keeps the prospect war chest entirely intact such that the team could use surplus talent to pull off a monster deal over the next year (Baez and one of Underwood/Johnson/Blackburn for Chris Archer and his pennies-on-the-dollar deal? Sure!).

I love this roster. So have at it. What do you like, what do you hate, and what do you think is just plain crazy?