Let me start off by saying that I take the "plan" aspect of this seriously. As the proverb teaches, no plan survives contact with the enemy. I expect the White Sox to be very active once again in the trade market. The "big" deals aren't something that's easy to project. I do not expect all of these moves to happen or even for close approximates of these moves to happen.
So this is the plan I would submit to Rick Hahn. That means I don't simply suggest the things that I would do but what I think would be reasonable to expect the White Sox to be willing to do. I expect to see more money committed but I don't think Hahn is going to solve all the problems during this offseason in some kind of "all-in" move. There are still going to be legit holes that need to be addressed but I'd aim for a lot of them to be capable of being filled in-season should circumstances around the trade deadline dictate going for it. This is a bit earlier than I usually like to consider offseason moves but here goes:
Arbitration-eligible (with projected salaries from MLBTR):
Contract options (pick up or buy out):
Listed first simply because, by sheer quantity of bullpen roster spots, at least one reliever signing is certain. I expect multiple waiver claim acquisitions, at least a couple of which are potentially major league ready. I see this offseason as being similar to last season where a ton of guys were brought in, particularly after non-tenders. And a Rule 5 pick should be used on a pitcher.
There isn't anything in the organization that can step in and potentially be a good contributor in 2015 (and probably not even in 2016). So I think this will be a focus but more likely addressed via free agency.
Another position where the organization simply doesn't have anyone to pair with Flowers. Ideally, I'd be looking for a catcher of starter quality. But a back-up is fine, as well, because I think the White Sox are fine with Flowers taking the majority of the starts in 2015.
The White Sox need to add some big(ger) bats and this is a good spot to try to find it. This is a lesser concern because the organization does have guys who can step in right away (e.g., Semien) and some guys who might turn out to be long-term pieces (e.g., Davidson).
Again, there are guys who can step in here and be fine - Sanchez, Semien, so on - but it's also a spot where an upgrade from what the organization has already can potentially be made. If they don't think they can address third base, they should go here as a fallback.
The White Sox don't sign free agent starting pitchers with pedigree. So I think it's unlikely they sign any of the ones on the market. ("Pedigree" ends with Brandon McCarthy.) The guys who might be available on one-year deals - Masterson, someone who unfortunately rejects a QO without thinking of how that affects his value, flyers in the Paulino vein, so on - I could see happening but I don't think it will be a particular focus in free agency. I do think we'll see some activity in the trade market but it's down this low because I'd say any activity would probably fall into the "big salary, not above-average production" category since that's what is most available. Also, I'm counting on Carlos Rodon being available to step into the rotation as early as late April but no later than mid June.
Now on to specific targets.
Nick Markakis. 4 years, $40 million. A pretty obvious target. The team needs someone who bats from the left-side to help balance the lineup. Beyond that, he makes contact and gets on base. He's got an above average arm and I think a move to left field in the Cell will be good for his overall defense. He may be getting to the point where a platoon partner would be advisable but, historically, he doesn't show much of a platoon split (just like Eaton). While I wouldn't necessarily endorse it, it wouldn't be a bad idea to bat them one-two. And, given that one should plan for Eaton to miss some time, not only does Markakis have experience in the leadoff positions, he also actually has the skill set to do so without embarrassment. In a reprise of the ever-popular "Kenny Always Gets His Man", I could see Torii Hunter on a one-year deal as a fallback. Aoki a possibility, too. Basically, one way or another, they're getting a left fielder.
Chase Headley 4 years, $56 million. He's a big upgrade defensively over Gillaspie. And his bat is above average. This contract values him at a bit more than 9 WAR over the contract. That may be light, depending upon one's perspective of his defense. I could certainly see him getting another $12 million or so and there being an argument for it being reasonable. Maybe I'd be willing to do that; I'd need more time to think that over, though.
Jeff Mathis 1 year, $2 million. Offense sucks but defensive skills add significant value. I could see some of the pitch-framer whores bidding him up some more. Free agency is a fallback because ideally catcher would be addressed via trade.
Asdrubal Cabrera 3 years, $25 million. As noted above, I'd rather address third base with a Headley or via trade but, failing that, I see this as a better execution (for more money, of course) of the Jeff Keppinger idea. I'd sign him to play second base but he's capable of playing shortstop or third base. He'll be turning 29 next month and he has a pretty clean health history. He's probably an average defender at second but he makes up for it enough with the stick. The contract essentially values him as a 4+ish WAR player over the course of the contract, which seems pretty feasible. Yes, the White Sox have a lot of middle infield options major league ready and at various levels in the minors but I don't think any of them are really of the "impact" variety other than Tim Anderson and the coming of his impact days is still measured in years.
In order of likelihood.
Trade Viciedo to Seattle for Jesus Montero. I don't really care for whom they trade Viciedo. This is really about trading an essentially valueless thing for someone else's essentially valueless thing. I think when I read that the Phillies were thinking about trading Domonic Brown that I said that was a trade that made itself. Another possibility is Jose Tabata, though the Pirates would probably have to throw in some other things like players to make that work. I like the Montero idea best because allegedly the Mariners like Viciedo, Montero isn't arbitration eligible, has a minor league option remaining and a straight up deal is plausible. Montero, of course, has a lot of warts - weight issues, dessert throwing issues and Biogenesis issues - but he was once one of the highest rated prospects so he's worth a flyer.
Trade John Danks for Edwin Jackson. I'm stealing this one from Ballantini. Another "problem for problem" trade. Both sides can argue that the other should kick something in, whether cash or players. Jackson (as always) looks good via fWAR so the Cubs can argue the results have been unfair to Jackson and why should they pay Danks' higher salary. The White Sox can just point to the results and the fact that he's always under-performed his FIP. In the end, I think it's just easiest to make it a straight up challenge trade. Danks probably is what he is at this point: an innings eater who is below average but a positive contributor. Jackson, on the other hand, may not be what he has been recently and I'll place my bet on Cooper doing his magic again.
Trade Jordan Danks for generic right-handed reliever who throws hard. This would be a minor move, of course. I think JorDanks would be a fit for a National League club and maybe could provide them with a bit of value off the bench. He's out of options and I don't think there's any need to reserve a roster spot for him. In return, the White Sox would get another warm body to fill out the bullpen, either immediately or a guy to put in AAA for depth. Maybe Generic would have some upside. Whatever.
Any of the positions I mentioned as targets could be addressed via trade, too. Making up grand trades isn't really my strong suit, though, so I'll leave specific trades out of it. However, I do like a lot of the targets others have mentioned in their plans like Jay Bruce or Jason Castro or Papelbon. In return, there aren't many names on the White Sox I wouldn't be willing to deal. So here are the players I'm not willing to part with (and now to cover myself) unless it's an utterly amazing and near-fantasy trade which pretty much would never, ever happen:
Sale, Quintana, Abreu, Eaton, Rodon, Anderson.
Obviously, that spectrum continues and eventually graduates to players I'd absolutely love to get rid of (like Viciedo). I'd be a lot more interested in hearing about a trade proposal involving him than, say, Alexei. And speaking of Alexei...
Alexei Ramirez: 2 years, $22 million. This essentially turns his $10 million 2016 team option into a guaranteed year and adds another year for $12 million. The total future commitment to him would then be 2015-17 for $32 million. Given his current contract, there are a lot of options for how to structure this - front load, back load, spread dollar increase over all three years or the final two or just the last. Alexei probably has at least two years left in him at shortstop and, even with a move to another infield position (or maybe even the outfield), he's a reasonable bet. And with Viciedo gone, and Nieto in the minors, Ramirez may well play a very key role in keeping Jose Abreu "comfortable". And I'm willing to pay for that. Obviously, Ramirez could command more than this if he were on the free market - I'd expect him to get 4 years easily and at a higher annual rate - but, of course, he's under team control for two more years. The discount seems like a fair amount to get 2016 and 2017 guaranteed.
In a lot of other plans, I see way too much money (and years) spent on relievers. I realize that 2014 leaves a sour taste and it looked like the White Sox didn't have anything in the minors to help but that was 2014. I think left-handed reliever is really the only thing the White Sox need to fill from outside the organization.
For example, I didn't see Chris Bassitt listed on many plans. He's a pretty sure bet to be on the opening day roster. If he's not traded away (which I would be aggressive in trying), Montas is pretty close to ready for a bullpen role. Nolan Sanburn is now in the organization. I think Rienzo can still be a decent reliever. There are others. I'd be fine with getting a Papelbon but I don't think the bullpen should have a lot of money and years showered on it simply because things didn't work out last season. That's how Scott Linebrink happens.
Same thing on the rotation, I just don't see money committed to anybody in free agency. I could absolutely see money added via trade.
Rotation: Sale, Quintana, Jackson, Noesi, [Chris Beck, placeholder for unnamed starter who is acquired, who is in turn maybe a placeholder for Rodon].
Bullpen: Petricka, Putnam, Duke, Bassitt, Webb, Cleto, Guerra
Disabled List: Jones
Obviously, he isn't going to be ready until well into the season, if at all.
We're going to see Rodon next season and probably by June. I certainly lean towards him being inserted into the rotation but by no means do I think that's a sure thing. Depending upon circumstances, I could see him eased in as a reliever for 2015. If a starter, and no injuries in the rotation, he'd take Noesi's or Unnamed Starter's spot.
[This isn't the batting order]
RF A. Garcia
Bench: Sanchez, Gillaspie, Trayce Thompson, Sierra, Mathis
I've included Cabrera not because I think both Headley and him would sign but because his salary is a useful placeholder for some other player(s) who I think the White Sox will acquire and will cost more money. Maybe both could happen but, more likely, you'd just be adding one of the league minimum middle infielders - Semien, Sanchez, Johnson - to second or third base and another one to the bench.
Notable, of course, is that I've included Thompson. Someone who could play center was needed with JorDanks gone and Thompson - long a favorite of mine so, yes, bias - is pretty good in any outfield spot and has the wheels to be a runner off the bench, too. I wouldn't recommend giving him many starts - Sierra should be used for those - but, alas, with Eaton that's probably not possible to comply with. So get ready for a couple dozen strikeouts for every moonshot.
Obviously, there's some major holes still. Not only isn't there a "recognized" DH but there really isn't anything that's worth "rotating" through because the bench is weak (at least offensively). I expect it will be used to rest the starting position players. But a DH-type wouldn't be hard to acquire during the season nor would better bench pieces. Anyway, there is some help on the way from the minors as, for example, Micah Johnson could be solid player, at least offensively, in 2015. And maybe Matt Davidson shows his 2013 form.
All told, I think this is about $96.1 million, inclusive of Paulino, Keppinger, Quintana's Super Two eligibility bump and Jones getting paid to be on the DL. There's a lot of built in flexibility for trade acquisitions, either in the offseason or in season. Please poke (or rip) holes in this, as I'm sure there's something(s) wrong in here since I didn't spend much time on it and it's pretty stream of thought.