With the 2019 season behind us, it is clear that the Chicago White Sox are a team with impressive young talent, major depth issues, and very low payroll commitments. If the money will ever be spent, then the time is now. Below is a position-by-position breakdown of the organization’s options to supplement the team’s young core with proven talent. First are the positions that are not likely to see additions.

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Third Base

Yoan Moncada is a star and one of the best players in baseball. Barring an extremely unlikely signing of Anthony Rendon, Moncada will be the team’s third baseman next season. Even with an extremely unlikely signing of Rendon, Moncada, who graded as the fifth-best defensive third baseman in baseball in 2019 per Fangraphs, should be the team’s third baseman next season. The only thing to watch for this winter is whether or not he and the White Sox agree to an extension. ESPN’s Jeff Passan hinted at this in August.

Shortstop

Any potential offensive regression that Tim Anderson may face in 2020 should be mitigated by the relatively high probability of his defense reverting to its 2018 form (or better). Anderson is without question the long-term White Sox shortstop, and his team options in 2023 and 2024 for $13.25 million on average are looking like bargains.

First Base

The White Sox are almost certainly going to re-sign Jose Abreu, which makes sense for a lot of reasons. He is expected to move to a designated hitter role once Andrew Vaughn arrives, but that may not happen until 2021. I happen to have a major prospect crush on Vaughn, who I think will fly through the system next year and be ready for the big leagues by the all-star break.

Short of re-signing Abreu, the first base position does not require much attention this offseason. Abreu will likely receive one or two years guaranteed, with team or mutual options tacked on at the end. It would be surprising if the guaranteed years exceed $12 million in average annual value, but it also would not really matter given that it would only last a year or two while the team payroll is a non-issue.

Left Field

Offensively, Eloy Jimenez had a monster finish to the season (who could have guessed that?). He produced a .900 OPS over his final 84 games.

His defense was, to put it nicely, not pretty. Nevertheless, he showed the ability to play left field at least competently over significant stretches. The fans who want him to be moved to designated hitter effective immediately seem to largely be the same ones who wanted Yoan Moncada to quit being a switch-hitter because of his 168 plate appearances as a righty in 2018. Chances are that Jimenez gets better in left field, to the point where moving him in the near future will be out of the question. While it is unlikely that he is ever a plus defender, he should at least be passable.

Second Base

Nick Madrigal is eligible to be called up without losing a year of service time as early as the team’s first homestand in April. He is also somebody I can envision agreeing to a Tim Anderson or Eloy Jimenez kind of extension before the season begins, as his style of play is not conducive to a massive free agent contract down the road. For the first couple weeks of the season, someone like Danny Mendick, Leury Garcia, or Yolmer Sanchez (if he is retained) will probably start at second base, but Madrigal’s eventual arrival renders a big second base signing improbable for the White Sox.

Center Field

See the second base paragraph above. Luis Robert will be eligible for a promotion without losing a year of service time during the first homestand of the 2020 season. A contract extension before the season seems unlikely, since Robert already has made significant money and, if he plays anywhere close to expectations, should get a very enticing contract as soon as he hits free agency. Leury Garcia or Adam Engel may draw starts in center field early in the season, but once Robert is promoted, he should be an everyday player.

Catcher

James McCann was a revelation in 2019, providing above-average offensive production from a demanding position while being an improvement defensively over recent Sox catchers. He is still under team control for the 2020 season, and it is probably a bit early for an extension to be seriously discussed unless it is extremely team-friendly.

In all likelihood, Welington Castillo will not be back with the team next year. Zack Collins is an option for backup catcher, but it is unclear as to how much the White Sox trust him behind the plate. Thus, there are a few different routes the organization can take for the catcher position. They can sign a veteran backup for a year or two to complement McCann and ease Collins’ workload to allow him to be the 26th player on the roster (a new wrinkle in 2020). In this scenario, Collins would get occasional designated hitter, first base, catcher, and pinch hit reps. Another option, however, is to sign a star in Yasmani Grandal. The Milwaukee catcher hit .246/.380/.468 with 28 home runs, a 121 wRC+, and 5.3 fWAR this season.

Grandal, who the Sox reportedly made a multi-year offer to last year, has a mutual option with the Brewers for 2020 that he will almost certainly decline — he may return to Milwaukee, but not on a 1-year, $16 million pact. If the White Sox choose to offer him a multi-year deal worth between $16 million and $20 million annually, perhaps his interest would be piqued.

The switch-hitting catcher is more than good enough at the plate to be the designated hitter on days when he is not catching. James McCann would likely catch those games. Spending a significant amount of money on a 31-year old catcher, however, does carry some inherent risk. If the Sox do not pursue Grandal, then veteran backups such as Alex Avila, Jason Castro, Robinson Chirinos, and Austin Romine are options to play catcher when McCann cannot.

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The positions below should see changes this offseason, as alluded to by the front office in recent weeks.

Relief Pitching

While the White Sox will address their bullpen this winter, just as every team does every year, writing about the state of the bullpen and potential targets is not very useful. Relievers are extremely volatile. Jace Fry was one of the best relief pitchers in baseball in 2018, but was average at best in 2019. Aaron Bummer spent most of his time in the minors in 2018, and was dominant for the White Sox in 2019. Aside from a few truly elite arms across the league, relievers are extremely difficult to project from year to year. The White Sox should seek a late-inning reliever such as Will Smith, but in-house options like Tyler Johnson and Codi Heuer could also help as soon as next summer.

Starting Pitching

Rick Hahn has expressed confidence in Lucas Giolito, Dylan Cease, and Reynaldo Lopez opening the 2019 season in the rotation. Other starters such as Michael Kopech, Carlos Rodon, and Dane Dunning should be factors during the season as they progress from Tommy John surgeries. Here are some potential additions the organization could pursue via free agency:

• Brett Anderson’s left-handedness would bring more balance to the rotation. The Oakland starter will be entering his age 32 season. He is a bit of a throwback pitcher, as he does not have overwhelming stuff, does not register many strikeouts, but also does not allow many walks. As a back-end starter, Anderson could come pretty cheap.
• Madison Bumgarner, another lefty, is still just 30 years old, but has logged 1,948 innings in his career (including postseason). While he is still good, he is not the kind of player the White Sox have typically been interested in, especially since he will likely be seeking a multi-year commitment that would exceed the largest contract the Sox have ever given a pitcher. It is also worth noting that Bumgarner holds some antiquated views on celebrations that may clash with the culture the White Sox have been creating.
• Gerrit Cole just might be the best pitcher in baseball and has some of his brightest days ahead of him, but until the White Sox show a willingness to pay what he would command — around 7 years and at least $200 million — a Cole signing is unfortunately a pipe dream.
• Gio Gonzalez, whom the White Sox originally drafted, still has strong peripherals and would not command a very large contract. He is a somewhat realistic option to be the #5 starter on next year’s team.
• Cole Hamels had a decent year for the Cubs and seems to be the type of pitcher that ages well. Much like Gio Gonzalez, Hamels is a short-term option to round out the back of the Sox rotation.
• Rich Hill is injury prone and entering his age 40 season. He has averaged 109 innings pitched over his last 4 seasons, but is actually very good when healthy. If the idea is to treat one of Kopech/Rodon and Hill as a starting tandem to get 200 solid innings from, then a Rich Hill signing could actually make sense. In order for this to happen, however the organization would also have to add other starters (perhaps two) with better track records of health. Regardless, the idea is intriguing.
• Dallas Keuchel is yet another left-hander (all the above pitchers are southpaws aside from Cole) past his prime, but he was available all of last winter and the White Sox never seemed to show serious interest.
• Corey Kluber has a $17 million team option and $1 million buyout for next season. With Cleveland missing the playoffs, could they look to shed salary and forego the option? It is unlikely, but possible, and should Kluber hit the open market, the White Sox would love to have his perspective in a rotation with Giolito, Cease, Kopech, and Lopez.
• Wade Miley fits the Gonzalez/Hamels mold of a left-handed back-end starter. Miley only averaged 5 innings pitcher per start this year, however, which is not exactly what the White Sox need.
• Ivan Nova ended up being a fine innings-eater for the White Sox this year, but is also a candidate for regression. He would be fine as a fallback option, but for now, the Sox should shoot higher for their #5 starter.
• Jake Odorizzi had one of the best years of his career for Minnesota this season. He will turn 30 in March, and could see a contract in the range of $10-15 million per year. If the White Sox want to upgrade their rotation a little more by adding a mid-rotation starter rather than a back-end type, Odorizzi is a name to watch.
• Hyun-Jin Ryu was lights-out for the Dodgers this year, but with over 2,000 professional innings under his belt and an extensive injury history, his market may not be as vast as his numbers would imply.
• Stephen Strasburg has been one of the most consistently dominant pitchers in baseballs for years, but if he opts out, he will expect to receive a contract close to what Gerrit Cole ends up getting.
• Julio Teheran has a $12 million buyout with Atlanta. He has been very consistent over his career and fits the Odorizzi mold as a fine mid-rotation addition.
• Zack Wheeler is another solid mid-rotation option, as he has flashed high-end starter potential in the past and does not have much mileage on his arm for his age. He may command something like 4 years and $80 million, but there is a lot of upside in Wheeler.
• Alex Wood was very good with the Dodgers, but only managed 35 innings pitched with the Reds in 2019 due to injuries. His injury history will lower his price tag, but it is unclear as to whether he will even be healthy enough to be depended on in 2020.

In addition to the above targets, the White Sox could also look to the trade market for starters:

• Yu Darvish has 4 years and $81 million remaining on his contract, and the Cubs are looking to shed salary this winter. He was fantastic down the stretch this season and should not have a high price tag due to his money owed.
• Marco Gonzales, who the White Sox have shown interest in previously, is a lefty for Seattle who brings value in his durability and lack of walks surrendered. He has 4 more years of team control, however, so he would likely cost a top-100 prospect.
• Jose Quintana, assuming the Cubs pick up his $11.5 million option, is another trade option for them if they shed salary. This time around, he would not cost an Eloy Jimenez or Dylan Cease.
• Caleb Smith of the Marlins was burned a bit by the juiced ball this year, but is still an intriguing lefty with 4 years on control and a higher ceiling than someone like Marco Gonzales.

Right Field

The White Sox truly have zero in-house options for a competent right field starter for the 2020 season, short of moving players around unnecessarily. They absolutely need to acquire a player for this position if they hope to contend next year. Here are their free agent options:

• Kole Calhoun may see his $14 million option get declined by the Angels. A competent right fielder, Calhoun would be an unexciting stopgap in right field, but still a vast improvement over the 2019 right field situation.
• Nick Castellanos is a productive hitter who figures to receive a rewarding contract (perhaps 4 years, $70 million?). He would slot in nicely for the Sox but does not improve the outfield defense nor solve the handedness problem.
• Corey Dickerson has been a solid left-handed bat throughout his career. As long as he is not the big acquisition of the offseason, he would still greatly improve the roster.
• Marcell Ozuna has been a streaky but above-average hitter for the Cardinals, but he seems destined to re-sign with St. Louis.
• Hunter Pence very randomly had an all-star season for the Rangers before missing the second half of the season due to injury. Banking on him to repeat his performance, however, seems risky.
• Yasiel Puig is an exciting player, but is not what he once was. While he would represent an upgrade in right field, the Sox should view him primarily as a fallback option.

In addition to the above targets, the White Sox could also look to the trade market for right fielders:

• Brian Anderson (no, not that one) has quietly been stellar for the Marlins over the past couple of years, but with team control through the 2023 season, it is unlikely that the Sox would want to pay what it would take to acquire him.
• Mitch Haniger could be the next piece to go during the Mariners’ eternal firesale, but with three more years of team control, he would not come cheap.
• Trey Mancini had a fantastic year for the Orioles, but much like Haniger, he will be expensive to acquire if Baltimore does not opt to build around him.
• Nomar Mazara is someone the Sox had interest in during the trade deadline, but he has been replacement level for his entire career without many signs of improvement. On the bright side, he should not cost nearly much as these other names.
• Brandon Nimmo may be the odd man out in a talented, lefty-heavy Mets outfield. He or Michael Conforto may find themselves in trade talks this winter, and for more, check out the full post I wrote about this a couple weeks ago.
• Joc Pederson has one year of team control left and has expressed displeasure with his role in the crowded Dodgers outfield. He should be relatively cheap and is coming off a year in which he hit 36 home runs and had a 127 wRC+.
• Gregory Polanco has had a disappointing career in Pittsburgh. Like Mazara, he would be a bit of a gamble, but he may be available.
• Giancarlo Stanton and his monstrous contract may not be as valuable to the Yankees anymore, and should they decide to move on, his trade value will be very low. It would be unprecedented for the White Sox to acquire a player owed $244 million, of course, but the Yankees would theoretically pay a significant amount of that in any Stanton trade.

Designated Hitter

The organization’s production from the designated hitter role last year was frankly embarrassing, and the acquisition of a true offensive force could go a long way towards making the entire lineup more formidable. There are not many in-house options for this role. Zack Collins cannot yet be trusted with such a large job, and Gavin Sheets will likely start the season in AAA. Yermin Mercedes may become a 40-man roster casualty, and Jose Abreu should be the starter at first base.

There is considerable overlap between the right field options and designated hitter options. The only truly unique designated hitter target is J.D. Martinez. All signs point to Martinez opting out of his contract with the Red Sox, and his free agent market should be very limited. Martinez is still one of the best hitters in all of baseball, as he is coming off a .303/.384/.557 season. He would be an excellent mentor to Jimenez, Moncada, Robert, Vaughn, and the other Sox sluggers. The question, as always, is whether or not the White Sox are prepared to be the highest bidder for his services.

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With all these options and financial flexibility, one would hope that the White Sox can capitalize on these circumstances and begin their contention window in 2020. Personally, I expect the team to spend — not on the Cole/Rendon level, but on significant talent. I have a very hard time envisioning the team entering the 2020s with some of the lowest inflation-adjusted payrolls in franchise history.

Specifically, I predict that the Sox will use free agency to address their need at designated hitter and to add pitchers. They would then be able to trade for a right fielder. I would be pleased with an offseason including signings of J.D. Martinez, two of Zack Wheeler, Jake Odorizzi, and/or Alex Wood, and a trade for either Joc Pederson or one of the Mets outfielders.

Feel free to comment with your predictions for the offseason, and thank you for reading! Writing this opened my eyes to a lot of potential targets that I did not previously consider, and I hope you had a similar experience while reading.