I was up rather late battling a bedbug infestation. It isn't too bad yet, but I did learn that Chicago is like the bedbug capital of the world, and that I'm very tasty. I guess the fact that two entire endcaps of the hardware store was dedicated to bedbug eradication is no surprise, then. It was fun to go full scorched earth on the condo and watch the little bastards die. Mwahaha.

Anyway, one of the late night links that I saw on Twitter was via the CCO about former Epstein/Hoyer disciples Jon Lester and Justin Masterson:

#Cubs: Cubs Have Reportedly Had Internal Discussions about Jon Lester and Justin Masterson http://t.co/BtYiTv4CTI #MLB — ChicagoCubsOnline (@TheCCO) July 26, 2014

Lester and Masterson are among the best available free agents, assuming they aren't extended, that the Cubs can splurge on this winter. It obviously makes sense given that the Cubs have an evolving offense that's waiting to burst forth into the majors, but need pitching to supplement Jake Arrieta considering that two other pitchers are sucking and most of the internal options are end-of-rotation guys. Given that these are former Red Sox, Theo and Jed know them fairly well and the internal discussions aren't a surprise. Unfortunately, Masterson is having a down season (bounceback candidate for cheap?) and Lester may consider returning to the Red Sox either via an extension or after he becomes a free agent post-trade, especially after the Sawx just traded Jake Peavy to the Giants. That does leave guys like Max Scherzer and James Shields. And there might be some veterans that could be picked up to prop up the outfield and third base until reinforcements arrive. Theo himself has suggested keeping veterans (especially those with club control) around to establish continuity and leadership.

While it is uncertain which free agent(s), if any, the Cubs will ink this winter, it is certain that they'll have tons of money to spend. The payroll this season is only $92.7MM per Cots, and next year, before arbitration raises and auto-renewals, there are only about $32.14MM committed. We can probably reduce this because Edwin Jackson's contract is only $11MM (he received a big signing bonus but most sites use his AAV in their calculations) and Kyuji Fujikawa is unlikely to get his vesting option, so let's drop about $7.5MM off that number and call it around $24.7MM committed, which takes care of Edwin, Starlin Castro, Anthony Rizzo, and Ryan Sweeney.

My guess is that James Russell and/or Wesley Wright is traded so let's wipe their arbitration raises off our books for the sake of this exercise. Travis Wood is sucking so he likely won't get much of an arbitration raise; let's go with $4.5MM to be conservative. Jake Arrieta is pitching like a madman but we'll keep his contract real here. I'm using Andrew Cashner's first arbitration contract as a comp, so Arrieta should get around $2.4MM. Pedro Strop made $1.325MM this year and has pitched well enough so we can set his next arb raise at no less than $2MM. That raises our 2015 commitment to approximately $33.6MM.

Among the position players, I think that the Cubs may tender Chris Coghlan, Justin Ruggiano, Luis Valbuena and Welington Castillo their contracts. Beef has been okay behind the plate (not spectacular, but he's the best option they have) so let's give him $2MM. Coghlan is hitting well after an early slump but we're going to keep it on the low side with $1.4MM just to even out my numbers because I can't math in my head anymore. Ruggiano has been on a tear when healthy so let's bump him up liberally to $3.5MM. Valbuena should probably get about $3MM. This puts us at $43.5MM before we consider auto-renewals and the guys on the 40-man roster. And this is just for 11 players!

That means we have to deal with 14 more active roster spots (CBA dictates at least $500K with a cost of living increase so let's up it to $520K just to be generous). 14 x $520K is approximately $7.3MM so that gets us to $50.8MM for the active roster.

15 more spots are available on the 40-man roster. The 40-man roster salary rules differ depending on service time and split-contract status (some players are optioned back and forth so will get paid depending on whether they're in the minors or in MLB). Let's just go with a nice round number of $50K for each guy who isn't active, and we get $750K, and since the Cubs are generous, we'll round that up to about $1.2MM and get a ballpark estimate of $52MM in commitments for 2015.

Even if the Cubs are still restricted by their debt repayment plan (see Bleacher Nation's awesome post for a breakdown of what happened here), a 2015 commitment of $52MM gives the Cubs $30MM to match the Oakland A's payroll for this opening day, and about $50MM to get them just beneath the Milwaukee Brewers, who entered the season at the halfway point of all MLB payrolls. This of course doesn't take into account the bid for Rusney Castillo, whom the Cubs are interested in this summer. It also doesn't take into account a potential bid for Asian pitchers like Kenta Maeda, should he become posted, or extensions that may be signed by existing players. But $30-50MM can buy quite a bit even in an inflated free agent market. The Cubs have a young nucleus that seems to have lots of promise and they don't have to spend like the Yankees to become relevant again.

So let's see what happens, because there are some guys worth spending on.

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