High Risk/High Reward – Jared’s Offseason Plan


From my perspective as well as the perspective of most White Sox fans, 2020 was scheduled to be the first year of contention. Even with an active offseason, this team is not ready to jump up and hang with the big dogs in October. New York could lose 25 players to injury and find a way to win 90+ games. Tampa and Oakland have shown with regular consistency that they can cook a 5-star meal with Aldi ingredients. Boston will find a way back to contention, even with their desire to shed payroll (which I could see the White Sox taking advantage of if the right offer presents itself). Houston is a juggernaut that is ahead of the curve in all aspects of professional baseball (analytics, player development, financial management, pro scouting, etc.) And a bit closer to home, Minnesota and Cleveland are in contention windows that, while unpredictable, sees them in consideration for the preseason AL Central title regularly.

All that being said, the White Sox are in prime position to take a major step forward. A step that will see them competing for the AL Central title and playing October baseball for the first time since *checks notes* sometime around the age of the dinosaurs.

Jerry/Kenny/Rick have ZERO excuses this offseason. The sting of last offseason still lingers. But a playoff contender can help put the Machado SNAFU in the rearview. Or the White Sox can cruise Instagram to find Gerrit Cole’s friends and family who play pro ball. I won’t be shocked either way.


  • Alex Colomé, $10.3M – Tender. I wish the Sox would’ve flipped him at the deadline. But going forward they’ll need help closing out games in late innings.
  • Yolmer Sánchez, $6.2M – Non-Tender. He’ll find work because of his glove. I’m not going to beat a dead horse on his offense.
  • James McCann, $4.9M – Tender. I worry that April-July this last season was an outlier, but at a premium position it’s well worth finding out.
  • Carlos Rodon, $4.5M – Tender. See more below.
  • Leury García, $4M – Tender. I LOVE Leury as a 26th
  • Evan Marshall, $1.3M – Tender.
  • Josh Osich, $1M – Tender.
  • Ryan Goins, $900K – Non-tender.


  • Welington Castillo: $8 million/$500,000 buyout – BUYOUT


  • Jose Abreu (made $16M in 2019) – Re-sign (see below)
  • Iván Nova (made $9,166,167 in 2019) – Adios.
  • Jon Jay (made $4M in 2019) – Adios.
  • Hector Santiago (made $2M in 2019 on split contract) – Adios.


No. 1: 2B Scooter Gennett (4 years, $36M. 5th year mutual option $10M). Anyone can look at Scooter’s 2019 season and call me crazy. Thinking about this addition the last several weeks I even found myself saying the same thing at times. But Scooter had a severe groin strain last year that derailed his season, coming off 2 seasons of great baseball including an all-star appearance. He is only 29 years old and his rough 2019 can end up being a bargain for the Sox at $9M AAV. At worst, he’s oft-injured but will provide professional AB’s when available. At only 4 guaranteed years, it’s worth the commitment.

No. 1: RF Yasiel Puig (5 years, $60M). Puig gets a bad rep for being a headache to deal with for a clubhouse. And it’s both unfair and unreasonable to assume that this won’t be the case when he’s playing alongside Moncada/Abreu/Robert simply because they all were born in the same country. However, Puig’s skill set along with the White Sox’s need in right field make this a good fit. It’s been 5 years since Puig broke out as a rookie combining for nearly 10 WAR over his first 2 years. But he is only 29 and has a rare combination of speed, power and arm strength to warrant a 5-year deal at an affordable $12M AAV.

No. 3: Yasmani Grandal (4 years, $60M. 5th year mutual option $16M). Grandal and McCann will be a great tandem at the catcher position. He’s also a switch hitter who can produce at both sides of the plate. He can work in the catching tandem or give Abreu rest at 1B.

No. 4: SP Madison Bumgarner (4 years, $56M. 5th year player option $14M). After watching this postseason domination, I see no situation where Jerry ponies up for Gerrit Cole to come to Chicago. Mad Bum is not the dominant pitcher he was back in 2011-2016, but he is still a workhorse who is fresh off a 200-inning season with a no-BS attitude that could help reel in the loose young pitching staff. He has experience pitching in the postseason and has seen firsthand both what makes a team great as well as what makes a team mediocre. The fifth year option is risky, but it’s the sweetener to get him to sign in Chicago.

No. 5: 1B/DH Jose Abreu (3 years, $24M). I’m hoping Abreu agrees to take a discount for the better of the team.

No. 6: SP Jhoulys Chacin (1 year, minor league). Rotational depth to start the year in AAA.

No. 7: RP Tommy Hunter (2 year, $5M). His 2019 was shot due to season-ending surgery. He’ll come back rested and hopefully an effective reliever.


No. 1: Trade Alec Hansen and a lower league lottery ticket to Pittsburgh for Chris Archer. Archer is a buy-low candidate that has struggled the last few years and Pittsburgh gave up FAR too much for him even at the time. This will cost the Sox $9M in payroll, but it gives Archer a clean slate in a new organization to pitch himself back into the form he showed in St. Petersburg. The White Sox aren’t a great organization, but anything is better than Pittsburgh right now. Reynaldo Lopez will be moved to the bullpen for long relief/spot starts and has enough stuff to get outs later in games as well.

No. 2: Trade Carlos Rodon to the Houston Astros for Josh James and Peter Solomon. I’d be fascinated to see what Houston can do with Rodon. He’ll be back just in time for their playoff push and can help them immediately. The White Sox get an opening day bullpen piece and a solid prospect.

No. 3: Trade Nick Madrigal to the Chicago Cubs for Kyle Schwarber. This will be contentious. I’m a Madrigal fan, and I think he’ll be a very good professional ballplayer. But the Sox need power hitting and Schwarber will thrive as a DH in a small ballpark without the worry of what to do if a ball is hit anywhere in his general direction in the field. He’s a perfect fit for the Sox needs and he’ll provide instant production for 2 seasons. Madrigal will be missed, but there’s enough holes in his game to warrant shipping him across town.


C – Grandal ($15M)/McCann ($4.9M)

1B – Abreu ($8M)/Grandal

2B – Gennett ($9M)

SS – TA7 ($4M)

3B – Moncada ($600K)

LF – Jimenez ($1.5M)

CF – Robert ($600K)

RF – Puig ($12M)

DH – Schwarber ($8M)

Bench – Garcia ($4M), Mendick ($600K)

SP1: Lucas Giolito ($600K)

SP2: Mad Bum ($14M)

SP3: Michael Kopech ($600K)

SP4: Chris Archer ($9M)

SP5: Dylan Cease ($600K)


R – Colome ($10.3M)

R – Herrera ($8.5M)

L – Osich ($1M)

L – Bummer ($600K)

L – Fry ($600K)

R – Marshall ($1.3M)

R – Lopez ($600K)

R – Hunter ($2.5M)

R – James ($600K)


Total payroll = $119M

Jerry is going to open the pocketbooks and Rick will turn this roster upside down. The entire league will take notice of the spending spree and trade activity. The entire front office is embarrassed about what happened last offseason and are going to come back with a vengeance. Jerry wants one more World Series as the owner and will get his wish just as we enter a new decade of White Sox baseball. As I said in the intro, this team is not ready in 2020 to compete with the big dogs. But the AL Central title will be won by the Chicago White Sox and this team is built to win for the next 3-5 years.

This team blends power, speed, excitement, hostility and fun all into one dysfunctionally functional roster. It could end in a dumpster fire, but it could also be one of the most fun teams to watch and a force to be reckoned with. It’s a roster built with high risk/high reward pieces. No risk it, no biscuit. It’s time to bring fall baseball back to the South Side.

Final record: 92-70, 1st place AL Central, 3rd seed AL playoffs

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Not bad ideas, but Rick Hahn would (hopefully) laugh Theo out of the building if he was offered Schwarber for Madrigal. I also don’t think Gennett would require more than 2 years and I even think the $9 mil AAV is high


4 years to Gennett and 5 to Puig is insanity. MLB contracts are fully guaranteed, no chance either players gets that long of a deal.

Madrigal has far more value than Schwarber.