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With Jon Lester, Jason Hammel and Miguel Montero In The Fold, Where Could the Cubs Go Next?

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The Cubs' roster has changed a lot this week. What other changes should come next?

Matt Marton-USA TODAY Sports

Let me start off by saying something incredibly important: let's all take a deep breath and give credit where credit is due. The Cubs committed to the rebuild with incredible tenacity. Whether you approved of the rebuild or not, they stuck to the plan for three years. When the tide began to turn as the team played basically .500 ball for much of last year after a dreadful start, our ears perked up. When the mega-kids began to arrive, we all took serious notice.

When the front office recognized the chance to strike without jeopardizing the plan at all -- the Cubs have spent cash on Jon Lester, cash on Jason Hammel, and cash and Jeferson Mejia and Zack Godley on Miguel Montero -- they took it and asserted themselves. Sure, there are enormous risks involved with committing big dollars to a pair of pitchers and a catcher in his 30s with back issues. But the franchise has added talent while subtracting only two low-level arms, only one of whom projects to provide significant value if it all clicks (even then, I suspect that the Cubs will find a replacement or three for Mejia this winter).

The Cubs' front office and ownership deserve credit for sticking to the plan, both by being such a terrible team for the last three years while using cash to obtain flippable assets and by flipping the switch this winter when the developmental timeline called for it. Let's all take a moment to enjoy the cohesiveness of this approach and its execution. It's really a thing of beauty if it's even vaguely appropriate to call tanking three years beautiful.

With those three big moves under our belt, I'd like to take a look at where the offseason could go from here. In particular, as I look at our roster and the changing landscape of teams around the league, here are three moves that I would be interested in seeing the Cubs complete.

Transaction No. 1: As part of a three-team deal, Cubs trade 3B Luis Valbuena, OF Chris Coghlan, C Welington Castillo, and SP Travis Wood to White Sox for SP Andrew Cashner and SS Franchy Cordero
The mechanics of this deal are tricky, but the fundamentals are clear and simple. The Cubs are about to push Valbuena to the bench with Kris Bryant taking over at third base, and Tommy La Stella was recently brought in to serve as a left-handed infield bench bat. Hmmmm. Coghlan will be pushed to the bench by a subsequent move (see below) and with Justin Ruggiano and Ryan Sweeney already there with more defensive value, Coghlan is the odd man out. Castillo is pushed into the short-side of a platoon, a role that will also be filled elsewhere (see less far below). And Wood -- already superfluous -- is made extremely superfluous by this deal. For the Cubs, moving these players constitutes moving spare parts.

The White Sox, on the other hand, have a few glaring needs: third base (no offense Matt Davidson), catcher (no offense Tyler Flowers), left field (they're trying to punt on Dayan Viciedo), and rotation depth. The Cubs are a ridiculously perfect match. It almost blew my mind when I realized it. For a team that is pushing all of their chips in the middle to compete in 2015, the Sox basically have to make this kind of move to avoid a few season-crippling holes.

That leaves us looking to what the Sox could use as currency. They won't want to move players off of their Major League roster, leading them to trade prospects. But the Cubs likely aren't interested in White Sox prospects, unless we're feeling sad about graduating all of our shortstops and we really want to grab Tim Anderson.

Enter the Padres. They appear likely to be heading for a massive rebuild. With Tyson Ross and Andrew Cashner now in the arbitration system, I imagine they're at least listening to offers. The White Sox could offer something like Anderson, Erik Johnson (as a rebound candidate), and Courtney Hawkins for Cashner. Anderson and Hawkins offer tantalizing upside and likely become two of the three or four best position player prospects in the San Diego system; Johnson is the sweetener. I'm not sure on the specifics between the Sox and Padres, but the point holds true for each team.

The Cubs get a risky starter with top of the rotation stuff and a short-season shortstop with projectable tools and a long path ahead of him. With a number of depth options in place, the club is well positioned to absorb a Cashner injury should it arise. The upside makes the risk worthwhile. Cashner would be under club control in 2015 and 2016.

Transaction No. 2: Cubs sign C David Ross
I don't know specific terms, but Ross should be inexpensive, maybe in the $2 million range. He either becomes Lester's personal caddy or serves the short-side of the platoon, replacing Castillo. This is not a sexy move. It's pragmatic.

Transaction No. 3: Cubs trade SS Javier Baez, CF Albert Almora, 1B Dan Vogelbach, and SP Felix Doubront to Rays for 2B Ben Zobrist and LF Wil Myers
If you're looking for a big bat, look no further than this deal. Myers won the 2013 Rookie of the Year award after posting an excellent .293/.354/.478 line across 373 plate appearances as a 22-year-old. 2014 was a complete disaster as a fractured wrist sabotaged his entire campaign, enabling him to play just 87 games and sapping his production when he was "healthy." Buying on Myers requires confidence that the freak injury was solely to blame for 2014's struggles and 2013 Myers is the real acquisition.

Adding Zobrist to the package is a fit for three obvious reasons. First, Zobrist is awesome! He's an elite glove at multiple spots, has plus on-base skills, runs well, and hits for enough power. Second, Zobrist is a Joe Maddon staple. Let's keep that pair together. Third, Zobrist could come in and mentor Arismendy Alcantara in a way that no other player in the league fully could. Yes, he's in his mid-30s, but Zobrist is also a stud who may very well sign an extension for the rest of his useful playing days upon completing the deal.

The cost to the Cubs is undeniably steep. I basically consider this deal to be Baez and Doubront for Myers with Almora and Vogelbach being traded for Zobrist. The price tag is likely a bit too high for the Cubs, so throwing in a guy like Ryan Brett or Taylor Guerrieri  (dear goodness: an earlier version of this story incorrectly listed Jake Odorizzi as the Guerrieri piece. That's what happens when you're going on two hours of sleep and just put your kid down after an extended cry. Sorry Jake!) from the Rays should be enough to even it out if necessary; Brett projects to be a very poor man's Zobrist in a year or two while Odorizzi has a big arm with some drug and injury red flags.

The payoff for the Cubs is also huge as it improves the 2015 roster substantially while punting the Baez strikeout risk for Myers' injury recovery risk. I think it's worth it.

This move would certainly test the revamped Rays front office as they'd be making a deal with a team they recently accused of tampering.

Where Would This Leave the Cubs?
Should the Cubs complete the deals listed above, they would project for the following 25-man roster in 2015:

Position Last First Salary
C Montero Miguel $12.0M
C Ross David $2.0M
1B Rizzo Anthony $5.0M
2B Zobrist Ben $7.5M
2B La Stella Tommy $0.5M
SS Castro Starlin $6.0M
3B Bryant Kris $0.5M
3B Olt Mike $0.5M
LF Myers Wil $0.5M
CF Alcantara Arismendy $0.5M
RF Soler Jorge $2.0M
OF Ruggiano Justin $2.5M
OF Sweeney Ryan $1.5M
SP Lester Jon $25.0M
SP Arrieta Jake $4.1M
SP Hammel Jason $9.0M
SP Cashner Andrew $4.3M
SP Jackson Edwin $11.0M
Long Wada Tsuyoshi $4.0M
Long Turner Jacob $1.0M
Mid Grimm Justin $0.5M
Mid Schlitter Brian $0.5M
Setup Ramirez Neil $0.5M
Setup Strop Pedro $2.4M
Closer Rondon Hector $0.5M
TOTAL $103.8M

So we're very clear: the above features Edwin Jackson on the roster specifically because his $11 million salary is guaranteed, not because I think he should be in the rotation ahead of Kyle Hendricks and/or Tsuyoshi Wada.

This is merely the manifestation of one out of the endless number of possible permutations for the roster this year. I show this to keep the mental wheels turning and to suggest that even though the roster retooling got its biggest boost with Lester, there are still plenty of opportunities for additional improvements.