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The 2018 White Sox were virtually unwatchable for most of the season. It's time to change that.

Going from 100 losses to true contention is probably a bridge too far for one offseason. But fielding a more competitive club that helps change the losing culture, and starting to align some pieces for a successful 2020 season is a bridge just right. Plus with the AL Central looking extremely weak this past year and Cleveland likely to lose a couple pieces in free agency, the Sox should try and position themselves to capitalize if the rest of the division falls short.

So, in short, I'm going to be aggressive. Probably more aggressive than is realistic. I want to see LOTS of new faces on the 2019 White Sox - some that make the team more watchable in the short term, and some that might help in the long-term.

ARBITRATION-ELIGIBLE PLAYERS

I think there's a chance that Avi re-captures some of his 2017 form, but I'd rather make a play for an outfielder with a higher floor and more team control. All the other decisions are pretty cut-and-dry in my mind.

CLUB OPTIONS

Shields was cromulent enough last season, but at this point cromulent is his ceiling - and unplayable is his floor. The Sox should aim higher. I'll talk more about Jones in a moment.

OTHER IMPENDING FREE AGENTS

Again, time to aim higher than MiGo. I know, it's weird to be a Sox fan and have actual aspirations. I added Santiago here, who provides good depth for a reasonable price as the last-ish man in the bullpen.

FREE AGENTS
In descending order of contractual value...

1. Sign C Yasmani Grandal for 4 years/$64 million
Despite a brutal postseason, Grandal figures to be one of the best values on the free agent market and happens to play a position the Sox have had trouble filling for the better part of a decade. He's arguably the best defensive catcher in baseball, adding 13 runs via framing and 9 runs via blocking/throwing in 2018. On top of that, his 116 wRC+ over the last four seasons ranks behind Buster Posey, Gary Sanchez... and no one else at the position. Baseball Prospectus rated him as the 20th most valuable position player in baseball in 2018, just behind Anthony Rendon. Have I made my case yet?

Grandal is likely to approximate 70% of Manny Machado's value at 20% of Manny Machado's contract. Whichever team signs him will get a steal, and if I were running the Sox I'd probably be willing to go over $100 million for him.

2. Sign 3B Josh Donaldson for 1 year/$26 million
I think it's likely Donaldson will be available on a high-salary one year deal. It's something of a boom-or-bust move, but even a healthy version of 2018 Donaldson would be an upgrade over Yolmer Sanchez. Donaldson gives the 2019 White Sox star power, watchability, and a higher ceiling, while buying time to figure out exactly how and when Nick Madrigal and Jake Burger might contribute down the road.

3. Sign SP Charlie Morton for 1 year/$22 million
Morton has openly contemplated retirement this year, indicating he probably won't want more than a 1-year deal if he plays. And I think he'll play if $22 million is on the table. I'm signing Morton with the same aims as Donaldson. He's likely to give the Sox 150 quality innings, take some pressure of the returning starters, and give them time to evaluate where every pitcher from Rodon down to Alec Hansen is headed long-term.

4. Sign SP Drew Pomeranz for 1 year/$6 million
Pomeranz is coming off a pretty horrendous season all-around. His walks jumped, his strikeouts fell, and his ERA was a Giolitesque 6.08 in 74 innings. However, he was worth 7.8 bWAR from 2016-2017 and doesn't turn 30 until November. He's the kind of back-end starter with upside that the Sox should be targeting.

TRADES

1. Trade UT Leury Garcia and OF Blake Rutherford to the Brewers for OF Domingo Santana
Santana spent this season shuttling between AAA and the Brewers bench, despite hitting 30 home runs in 2017. He strikes out a lot and doesn't play great defense, but the same can be said about Avi Garcia -- and Garcia doesn't have a .261/.349/.458 career line. With Christian Yelich, Lorenzo Cain, and Ryan Braun ahead of him on the Brewers depth chart, he'll once again be competing against Keon Broxton and Eric Thames for their 4th OF role. So I'll happily break up Milwaukee's major league log jam and Chicago's minor league log jam at the same time, in the hopes that the 26-year old Santana (who doesn't become a free agent until 2022) can build on his 3-win 2017 season.

2. Trade RP Nate Jones to the Dodgers for CF Andrew Toles
Jones likely doesn't have much trade value, but he should be enough to nab Toles, who's even more buried on the depth chart than Santana. Toles has had a weird career. But he's a legit centerfielder who hit .294/.341/.483 in 217 major league PA's across 2016-2017, numbers that are backed up by his .309/.344/.471 career AAA line. I see Alejandro de Aza-type potential in acquiring him -- and if nothing else he'd spare us watching Adam Engel hit for a while.

3. Trade C Welington Castillo to the Red Sox for UT Bag of Balls
Obscured by the deep lineup that's powered their World Series run, Red Sox catchers quietly turned in the worst offensive performance in the majors - to the point that Castillo's modest 95 wRC+ would be a 51 point improvement. I'm making this trade to get Castillo's salary off the books, so I don't really care who I get back. But if they'll part with a semi-interesting reliever like Carson Smith, all the better.

SUMMARY
Here are your 2019 Chicago White Sox, come mid-April:

LINEUP
CF Andrew Toles
RF Domingo Santana
3B Josh Donaldson
1B Jose Abreu
C Yasmani Grandal
LF Eloy Jimenez
DH Daniel Palka
SS Tim Anderson
2B Yoan Moncada

BENCH
OF Adam Engel
IF Yolmer Sanchez
C Omar Narvaez
UT Matt Davidson

ROTATION
RHP Charlie Morton
LHP Carlos Rodon
RHP Reynaldo Lopez
LHP Drew Pomeranz
RHP Lucas Giolito

BULLPEN
LHP Jace Fry
RHP Juan Minaya
RHP Ian Hamilton
RHP Dylan Covey
LHP Caleb Frare
RHP Carson Fulmer (out of options)
LHP Hector Santiago
UT Matt Davidson!!!

Payroll: $112 million

My back-of-the-napkin math says this is about a .500 team, with potential for more if guys like Moncada or Giolito take a step forward. The lineup is approximately 1 trillion times better than last year's, and the defense should play up a bit with Grandal's help.

Honestly, this is more moves than I reasonably see the team making this offseason, but none of them feel particularly unrealistic in isolation. I've added a ton of payroll, but $70 million of it comes off the books after the season so it won't hamstring the team long-term. And the only future piece I've lost is Rutherford, who I like but will be lucky to turn out as good as Santana.

This team should be much better and much more watchable than the motley 2018 crew. But go ahead and pick it apart in the comments.

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