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The Sox are basically right back where they were before their pre-2015 buildup and post-2016 teardown. Kudos to Rick Hahn and company for going 3-for-3 on the most important trades of the rebuild and returning to square one. Now comes the important question—how will this time be any different? I honestly don't know.

Two big problems sank the 2015-16 Sox: failing spectacularly with their splashy acquisitions, and having no depth to compensate. As far as I can tell, those problems haven't gone anywhere. You can already see the depth disappearing—a once promising farm system has been ravaged by injuries and marred by poor performances. After the Sox built one of baseball's best systems through trades, they completely failed to replenish it from within. By midseason next year, it will be one of baseball's worst once again.

At the end of a rebuild, you expect a team to load up on major league talent using the two resources it's been stockpiling: cash and prospect capital. But the Sox haven't even flipped the switch, and already they find themselves without a prospect surplus. Already, almost every young player in the organization is critical to the team's chances of winning in the near term. That's not a good position to be in, because it narrows path to contention.

That's why I see this as the opening of a four-year window of contention. In four years, Yoán Moncada and Lucas Giolito will become free agents, and the window will slam shut. We can't expect the Sox to extend their window beyond that, given their many ineptitudes. At the same time, we also shouldn't be making moves for 2020 that don't help the team in 2021, or actively harm them in 2022. We need to give the Sox every chance to win while Moncada and Giolito are still here.

Of course, that means we need to rely mainly on cash to get us where we need to go. If Jerry Reinsdorf fails to significantly ramp up the payroll, and he's instead content with the same half-measures that previously got the White Sox mired in mediocrity, then we might as well give up now and order our Yankees hats. But in this alternate reality, at least, the money will be spent.

ARBITRATION-ELIGIBLE PLAYERS

Alex Colomé, $10.3MNon-tender. I doubt this will actually happen, because it would require the front office to swallow their pride and admit that trading Omar Narváez for an expensive reliever was an iffy move, even before Colomé started looking shaky in the second half. I can think of lots of better ways to spend this money.

Yolmer Sánchez, $6.2MNon-tender. I love Yolmer's personality, but he's officially gotten too expensive. Most of his production can be replaced on the cheap.

James McCann, $4.9MTender and trade. He's got value, but it will be put to use elsewhere.

Carlos Rodón, $4.5MNon-tender. Rodón can't be counted on given all the injuries, and as he gets more expensive and closer to free agency, it gets harder to justify keeping him around. I'd re-sign him for less if he's open to it, but there will be enough pitching by the end of this to make him superfluous. Get well soon, big guy.

Leury García, $4.0MTender. He's not going to wow you with his bat or his glove, but if one of your starters gets injured he'll step in and be adequate. García is exactly the kind of depth you want on a good team to avoid the kind of negative WAR black hole the Sox always seem to get sucked into.

Evan Marshall, $1.3MTender. Keep him out of high-leverage situations, though.

Josh Osich, $1.0MNon-tender. He's done an admirable job eating innings, but hopefully we don't need him for that anymore.

Ryan Goins, $900KTender. He can stay for now, but he won't be here the whole season.

CLUB OPTIONS

Welington Castillo ($8.0M/$500K) – Half a million should be enough to buy a decent supply of erythropoietin.

IMPENDING FREE AGENTS

José AbreuRe-sign (2 years, $30 million). I doubt that Abreu would require a longer or more lucrative commitment than this, and I doubt that such a commitment would be wise, but I don't think there's any universe out there where this move doesn't happen.

Iván NovaLet go. Much as I'd like to keep Nova behind glass in case of an emergency, he deserves to go to a team where he can have a larger role.

Jon Jay, Hector Santiago – [Vomit emoji]

FREE AGENTS

No. 1: Zack Wheeler (4 years, $80 million). Wheeler can provide top-of-the-rotation pitching for less than half the overall commitment that Gerrit Cole will require. This is not a team that's one superstar away, so I think the best approach is to spread the money around and fill the roster with good players instead of going back to the stars and scrubs model. Wheeler fits well into the four-year timeline, is only 29, and doesn't have a ton of mileage on his arm.

No. 2: Yasmani Grandal (4 years, $76 million). Super original, right? Tons of Sox fans have already expressed interest in Grandal, but that's because he just makes too much sense for this team. Power? Check. Can hit from the left side? Check. Plate discipline? He only had the second-highest walk rate in baseball (17.2%). While catcher is not the Sox's position of greatest need, Grandal is the perfect offensive fit, and the fact that he's also one of the best defensive catchers in baseball is an added bonus.

No. 3: Tanner Roark (3 years, $33 million). Roark is vastly underappreciated for the stability and consistency he's shown as a starting pitcher. If he can provide the same kind of 2-3 WAR performance that he's given the Nationals and Athletics, he'll stabilize the back end of the White Sox rotation and give them flexibility in filling out the rest of the staff.

No. 4: Dellin Betances (1 year, $10 million). I'm basically swapping Colomé out for a different reliever with a lot more upside. Betances will be looking to rebound from a season in which he stayed on the mound for all of 8 pitches. He spent most of the season dealing with a bone spur in his shoulder, made it back to the Yankees in September, then tore his Achilles in his first game. Surely this is not the free agency he envisioned a year ago, so I'd have to think he'll look for a one-year deal to try to get back to health and reset his market.

No. 5: Arodys Vizcaíno (MiLB contract, $3 million MLB salary). Another reliever looking for a bounceback, Vizcaíno opened the 2019 season as the Braves' closer but went down to shoulder surgery in April. He'll turn 29 in a few weeks and has spent several years as a high-leverage reliever in the Atlanta bullpen. I'd be willing to make this a one-year major league deal if necessary.

TRADES

No. 1: Trade Kelvin Herrera to Texas for Shin-Soo Choo and $2 million. Although technically a trade, this is another move where the Sox can use their cash to acquire talent. At 1 year and $21 million remaining, Choo's contract is underwater, but he's still a good hitter and an on-base machine whose OBP the last two years has been .377 and .371. Sending back Herrera and the $9.5 million remaining on his deal helps to offset the cost.

No. 2: Trade James McCann to Atlanta for Greyson Jenista. With Grandal in the fold, McCann is now expendable, so I'm shipping him off to Atlanta to team up with Tyler Flowers behind the plate. The return is Jenista, a 22-year-old, 6'3", left-handed hitting right fielder. A second-round pick in 2018, he's still age appropriate for Double-A and could be a nice fourth outfielder in a year or two.

No. 3: Trade Andrew Vaughn, Luis González, and Bernardo Flores to Seattle for Mitch Haniger and Sam Tuivailala. Remember when I said the White Sox lack the prospect surplus to acquire major leaguers? I consider Vaughn to be the lone exception. He's the one bullet the Sox can fire to improve right now, since he's not important to the team's plans for 2020. As such, I'm making him the centerpiece in a deal to acquire Haniger, a patient hitter and a good right fielder with three years of control. Also coming back is Tuivailala, a veteran right-handed reliever with a four-pitch mix.

SUMMARY

There's enough talent at the top end of this roster to see a competitive team without having to squint too hard. There are no gaping holes in the lineup or on the pitching staff. There's enough depth to cover for a couple injuries and to push the second-tier players into part-time roles. Guys like Leury García and Zack Collins are a troublesome Plan A, but a perfectly fine Plan B.

We don't have much of a choice but to pin our hopes on Luis Robert and Nick Madrigal, but now they can hit eighth and ninth and develop under reduced pressure. Robert will be patrolling center field come April, but ideally I'd like to see Madrigal get another month or two at Charlotte. In the meantime, Danny Mendick can start at second and Ryan Goins can keep his spot on the bench warm.

I realize that the team currently has six starting pitchers, but I expect the rotation to sort itself out. Chances are that either one pitcher will get injured, or one of the young guys won't look so hot in the spring. If all six are healthy, Reynaldo López is likely the odd man out; he'd either get optioned or sent to the bullpen, depending on what's best for his growth and whether the team is in a pennant chase.

By my calculations, the payroll comes in at about $120 million, with $76 million committed in 2021 as the core reaches arbitration.

Lineup:
DH Shin-Soo Choo (L)
3B Yoan Moncada (S)
1B José Abreu (R)
LF Eloy Jiménez (R)
C Yasmani Grandal (S)
RF Mitch Haniger (R)
SS Tim Anderson (R)
CF Luis Robert (R)
2B Danny Mendick (R)/Nick Madrigal (R)

Bench:
Leury García (S)
Ryan Goins (L)/Danny Mendick (R)
Adam Engel (R)
Zack Collins (L)

Rotation:
Lucas Giolito (R)
Zack Wheeler (R)
Michael Kopech (R)
Tanner Roark (R)
Dylan Cease (R)

Bullpen:
Dellin Betances (R)
Reynaldo López (R)
Aaron Bummer (L)
Arodys Vizcaíno (R)
Sam Tuivailala (R)
Jimmy Cordero (R)
Jace Fry (L)
Evan Marshall (R)

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