Last year, I wrote a now-embarrassing piece about how the best course of action for the White Sox was to sign Trevor Bauer and trade for Anthony Santander. The latter went on to have an injury-laden season with career-worst numbers, and the former hasn’t pitched in a baseball game since June due to a lingering sexual assault case that the league — and local authorities — are still investigating. The ceiling for Santander remains high, but Bauer may never pitch in the big leagues again — and the Sox won the lotto on a $3 million prove-it deal with Carlos Rodón.
Shame on me.
But with glaring holes in right field and second base, the Pale Hose have a lot of work to do in order to get back into championship contention, and I’m keen to improve on my ability to project what will work best for a team desperate to, well... improve.
Knowing their counterparts in Minnesota, Detroit, Kansas City, and Cleveland, no one in the AL Central is going to sit idly by and let the Sox continue to dominate the division unchallenged. In order to ensure that they remain the apex predator of the division, Rick Hahn and company need to rectify the poor trade deadline decisions they made in 2021 by supplementing the roster with some much-needed help. Here is a look at how the Sox can best address that very issue.
Fool Me Twice: Right Field
There’s a lot of speculation over the best course of action, but the No. 1 goal should be to either bolster the lineup with a monster bat or shore up the defensive play in the right corner. The White Sox have been bottom 5 in the league at this position for years. With a fairly weak outfield market, the Sox will have their hands tied trying to decide how to handle it. Hopefully, they’ll do a better job than their decision to bring back Adam Eaton in 2021.
Castellanos is not a very good defender, but his bat is so exceptional that it wouldn’t particularly matter. Slotting in Castellanos to the middle of an order that already boasts Tim Anderson, José Abreu, Luis Robert, Eloy Jiménez, Yoán Moncada, and Yasmani Grandal would be terrifying for any pitching rotation in baseball. Castellanos has also publicly praised the South Siders for the team they’ve put together and has a rapport with team leader Tim Anderson.
He would even make a remarkable amount of sense defensively in that he would give Gavin Sheets and Andrew Vaughn opportunities to play in the field while Castellanos rests his legs and hits as a DH. But as a client of Scott Boras, this option doesn’t feel particularly realistic, especially knowing the kind of money he’ll likely make after opting out of his deal with the Reds.
Like Castellanos, putting Bryant in the middle of the Sox order would be terrifying for opposing teams. He also has playoff experience, a great attitude, and positional flexibility, something the Sox sorely need. But with Boras as his agent, too, Bryant is not likely to end up in a White Sox uniform with suitors like the Yankees, Dodgers, Giants, and Red Sox all vying for his services.
After a less-than-stellar exit with the Cubs, it’s clear Bryant will likely be seeking a deal close to the $300 million mark, and the White Sox have other options that fit their needs better if they’re going to spend anything remotely close to that kind of money. As much as it would be exciting to bring KB to the South Side, it just doesn’t seem likely.
With one of the best defensive WARs in all of baseball, perhaps no one on the market would give the Sox a better defender in right field. Add to that a massive amount of power that would buoy a White Sox lineup desperate for more deep balls and some newly-minted playoff experience that turned into a championship in Atlanta, and it’s clear Duvall makes perfect sense. Knowing what Jerry Reinsdorf likes to spend (or doesn’t like to spend, as it were), someone like Duvall is a best-case, realistic scenario on the South Side.
We don’t yet know if Duvall will even be available; he declined his mutual option with Atlanta and has become arbitration-eligible. The Braves might very well pony up and keep him there despite Ronald Acuña Jr. returning from injury in 2022. But if Duvall does decide to play the market, he projects a salary in the $9-$12 million AAV range. That’s a number the White Sox should happily pay.
A lefty with great contact skills and a temperament that handled playing in New York City, Conforto makes a lot of sense for more than a few reasons. Additionally, he moves well for his size, plays decent defense, and runs the bases with intelligence despite not being particularly quick on his feet. But a poor showing offensively in 2021 likely hurts Conforto’s contract ceiling, and the Sox are not a team that overpays for a player.
Chances are, a team with more financial flexibility will pursue Conforto as more of a franchise cornerstone player than the Sox, who would likely slot him in at the bottom of the order and give games against LHP to Andrew Vaughn. Sadly, for as many reasons as there are to sign him, there seem to be even more reasons not to.
Marte isn’t a true right fielder, but he’s adept enough at center field and has a good enough arm that he would make the transition well. The perennial Gold Glove threat would add excellent base-running skills to a team that needs some improvement on the base paths and he had as good a season offensively in 2021 as any year in his career. The stolen bases he could provide alone would make Tony La Russa’s mouth salivate.
But at 34 years old, Marte didn’t exactly instill confidence that he’s a viable option for a contender, as he helped the A’s skid right out of playoff contention in the second half this year. If he’s willing to play at cost for a team in contention, Marte’s speed, defense, and sharp eye at the plate might be just what the South Side needs. But if he’s looking for a big contract, he won’t find it in Chicago.
The newly-minted World Series MVP took a big leap from the fledgling Kansas City Royals to the World Series Champion Atlanta Braves. While in KC, Soler was a Sox killer, ruining many days for Chicago fans with his potent power bat that lifted him to 48 home runs in 2019. But Soler is not a great hitter if he doesn’t make perfect contact (hitting just .192 for the Royals before being traded). Furthermore, his power comes in spurts, often going long stretches without consistently hitting the ball deep.
Given his recent success in the postseason, Soler is going to get a big, well-deserved pay raise, but the Sox would not be wise to overpay for someone who looks a lot like the players they already have: Another right-handed power hitter who strikes out a lot and plays middling defense. Ultimately, Soler will most likely not be worth the contract he will command this offseason.
Pederson was almost a South Sider in 2021, after allegedly turning down a significant offer to play for the White Sox before Rick Hahn and company moronically exited negotiations to sign the pathetic and aging Adam Eaton. But after proving himself as a viable left-handed power bat for both the Cubs and the Braves this past year, Hahn might have to take another look. Joc would bring a remarkable playoff pedigree to the Sox if he joined the roster, most notably hitting home runs in 15% of his postseason at-bats.
But Pederson has never really been a full-time player, nor has he regularly manned right field. Furthermore, he’s as high a strikeout risk as anyone on the market and a very poor hitter against lefties. Dollar for dollar, Hahn might have been wrong about Eaton, but he might have been right about Pederson. Striking a deal with Joc seems to be reliant on whether or not the Sox add other depth in right field first. Perhaps if the Sox took a page from the Braves book and brought in multiple outfielders (i.e. Marte and Pederson), this would make more sense.
The Madrigal Dilemma: Second Base
After what will surely go down as one of the worst trades in team history by acquiring Craig Kimbrel for Nick Madrigal and Codi Heuer, the White Sox are forced to fill in the enormous gap he leaves at second base. A foundational player to man the middle infield with Tim Anderson needs to be a priority for the White Sox front office after trading their fourth overall pick in the 2018 draft — that is, unless they want another year of forcing Leury García to split playing time with Danny Mendick and Jake Burger.
(Do we really want La Russa batting Leury Garcia in the middle of the order for another 100+ games?)
The second base market is pretty sparse, but there are more top-end shortstops hitting free agency than perhaps any year in the history of the league. If one of them is willing to be flexible about their place on the diamond, the possibilities grow immensely. These are the best bets the Sox can make use of from the free agency market to rectify this issue.
Fresh off his career-best season and newly minted as Boras’ biggest recent client acquisition, Semien is in for an astronomical payday. The former White Sox draft pick was traded to Oakland during the team’s lean years and blossomed as one of the most impactful middle infielders in Major League Baseball. A sure-handed defender with a high baseball IQ and a well-respected presence in every clubhouse he joins, Semien also boasts remarkable plate vision and discipline, not to mention a lot of power.
After betting on himself with a one-year deal in Toronto, he hit a record-breaking 45 home runs as a second baseman and helped define the Blue Jays as one of the most formidable hitting lineups in the majors. Because of all this, he’s likely priced himself out of the White Sox’s spending limits. His age is of some concern; at 32 years old in 2022, he’s certainly not going to sustain his prime for the next decade. It’s also worth noting that the Blue Jays played two-thirds of their season in a Triple-A ballpark; perhaps a full-time return to major league ballparks would stagnate those power numbers. But if Semien is open to a short-term deal with a championship contender and a homecoming with the team who gave him his first shot, he would make for a splashy presence in Chicago’s already-impressive lineup.
This is a bit of a pipe dream, but if the White Sox are willing to pay true shortstop Semien to stay at second base, they might as well consider paying for Seager to make the switch. A left-handed power bat with tons of playoff experience and championship pedigree, Seager is maybe the second-best hitter on the free-agent market. Moreover, at just 28 years old Seager is just entering his prime and will be effective for the better part of the next decade.
The Dodgers traded for Trea Turner this year, and paying both of them what they deserve seems highly unlikely, even for the Dodgers. Meanwhile, the White Sox have the financial flexibility to make Seager their franchise player and he would fit the team’s many needs perfectly. There are a lot of teams that need a shortstop, but there’s a heavy saturation of middle infielders available this year, including perhaps the greatest free-agent class of shortstops in league history — and Seager is not a great defender. Maybe a move to the other side of the infield is just what he needs.
Plus, the Sox are never going to pursue Carlos Correa. The fans hate him for his history with cheating and his arrogance. Besides, he’s likely going to get one of the biggest deals in league history — if not the biggest — after a resurgent year in Houston. And there’s no way he’d play anywhere but shortstop.
Seager saw an injury cause his numbers to dip in 2021; this is convenient because he could have easily commanded a contract north of $300 million had he played up to his potential. Plus, slotting Seager into a Sox lineup that already boasts six-plus hitters would terrify the opposition. If the Sox play their cards right and are willing to open up the checkbook, they might be able to get Seager for a great price, even if it would make him the highest-paid player in team history. And they’ll have to: Boras is his agent. But if the Sox were willing to make Bryce Harper a $300 million man, Seager would accomplish a lot of the same offensive needs for less money — and he might actually say yes.
Like Semien and Seager, Story is a true shortstop, but if he wants to win, Story should be amenable to playing either side of the middle infield. Truthfully, he might be a better fit at second base, but his defense is so exceptional that maybe Tim Anderson would consider shifting over to make room for him. Story struggled to find his groove in 2021, but the young stud is just 28 years old and is capable of hitting 30 home runs and stealing 30 bases every year.
His dip in statistical output this season was mostly due to injury, but it makes him slightly more affordable and he’d make for a formidable presence at the top of an already-potent Sox order. But with the Yankees, Tigers, Phillies, Cubs, Angels, Rangers, and Rockies all vying for his services, a price cut for his career-low slash line in 2021 might not be realistic for the front office. Plus, the Sox already have two speedy, right-handed hitters at the top of the order. It’s clear why Hahn decided not to overpay for Story at the trade deadline.
The White Sox have long been linked to Báez, famously targeting the youngster in a trade with the Cubs that never happened during their rebuild. Defensively, Báez sometimes looks like a magician at shortstop, but the transition to second base proved to be effective with the Mets, limiting his throwing errors and utilizing his remarkable range and arm strength on the right side of the field. But his bat is just terribly inconsistent.
If he could rein in his plate vision and see the ball a little better, Báez has MVP candidate capabilities and 40+ home run projections. Alternatively, he can easily strike out 200+ times per season and his emotions easily get the best of him.
If his offensive struggles affect his contract negotiation potential, he could make for a very interesting option for the White Sox, and one that would make the middle infield in Chicago among the best defensively in baseball. The question will be whether or not it makes sense to add another right-handed power bat who strikes out a lot to a lineup that has far too much of that already.
Then again, maybe hitting later in the order would help Javy find his stroke again — and regain his MVP caliber play.
In terms of realistic options that fit, perhaps no one at any position makes more sense than Taylor. Able to play myriad positions on the diamond, giving him a true everyday role at second base would allow for him to get a rhythm defensively and focus on his abilities at the plate. He showed flashes of offensive brilliance this year, hitting well in the clutch for the Dodgers on a regular basis in the first half of the season. And while his numbers took a dip in the second half, he was still effective at the plate and capable of hitting anywhere in a stout Los Angeles lineup card.
His ability to play right field might also make him a prime target for the South Siders, as he could give the front office confidence in Andrew Vaughn and Gavin Sheets testing their mettle in the outfield. But if either one doesn’t work out, Hahn will be scrambling at the deadline to fill another hole with valuable prospect capital. And if it’s anything like it was last year, it likely won’t work out well enough to carry the team to a championship.
Escobar spent time with the White Sox before, just like Semien, and he does make a fair amount of sense in terms of what Chicago wants and how they intend to accomplish that. Of all the options on the market, Escobar will likely be the most affordable option that Chicago will target.
Furthermore, he’s been a pretty consistent offensive force over the last several seasons. He also can play anywhere in the infield, giving rest opportunities to the core and proving more veteran leadership on a team that can’t rely on Anderson and Abreu to carry all the weight of the crown anymore.
But Escobar will be 33 next season and he played pretty poorly in the second half of 2021. He’s past his prime and all metrics indicate he’s in for a statistical downturn in the near term. Relying on Escobar to fill in the gap at second base feels like a half measure at best — and a repeat of what happened with César Hernández and Adam Eaton in 2021 at worst. The juice here just doesn’t seem worth the squeeze.
Best Case Scenario: Corey Seager & Nick Castellanos
This is truly a fantasy for White Sox fans, but if Jerry Reinsdorf really wants to see his White Sox compete at the highest possible level once more in his lifetime, there is no better path for him to take. In order to bring in both of these elite bats, the Sox will easily cross the $200 million mark annually in terms of the salary cap, but what they’d get in exchange is five to seven years of baseball dominance. No one in the majors would compete with the White Sox in terms of offensive talent, and with the major league roster set for years to come, they could focus on rebuilding their quickly-weakening farm system to sustain their success long-term.
Just imagine opposing teams seeing this lineup card in the postseason next year:
R Tim Anderson SS
R Luis Robert CF
L Corey Seager 2B
R Nick Castellanos RF
R José Abreu 1B
S Yoán Moncada 3B
R Eloy Jiménez L
S Yasmani Grandal C
R/L Andrew Vaughn/Gavin Sheets DH
TA7 remains the best spark plug atop any order in the majors, and Robert will flourish hitting second if Seager and Castellanos are behind him. Abreu, Jiménez, and Moncada would all benefit from hitting a little later in the lineup, but 3-8 is completely flexible based on whoever is hot and cold.
It’s also fair to argue that Abreu is a true 5-hitter now; he doesn’t have the power he once did, but he would still get massive RBI opportunities and be able to focus on finding gaps in the defense rather than driving the ball in the air. Moving Grandal down in the order would help save his legs (allowing him to sit less), and Jiménez could build up the confidence to hit in the middle of the order in the future while getting to see higher pitch counts as he grows at the plate in the present.
Plus, that would leave Sheets and Vaughn to rotate for the best 9-hitter slot in the league. This team could easily hit 300+ HR in a season and the White Sox would be World Series favorites for the next half-decade. It won’t be cheap, but it would be worth it. And after seeing the fans arrive in droves this past season, the least Jerry could do is give them — and himself — the best chance to win.
Wouldn’t It Be Nice: Kyle Schwarber and Chris Taylor
Assuming the Sox don’t break the bank but also don’t cry wolf about their finances, pulling Kyle Schwarber in to play Right Field might be just the ticket. The tenacious left-handed masher went absolutely bonkers offensively in 2021, hitting 12 home runs in just 10 games for the Nationals. His offensive prowess was sustained after returning from a hamstring injury and being traded to Boston; he finished the season slashing .266/.374/.544 with 32 HR and 71 RBI. (And only that few because he missed 50 games.)
He also showed pretty tremendous defensive flexibility, playing all over the outfield and at first base. His bat and playstyle would fit the White Sox perfectly — and the hitter-friendly ballpark on the south side might give him his best chance to compete for a championship and sustain his exceptional statistical output.
Chris Taylor, meanwhile, would give the Sox another impact bat, but without breaking the bank. Like Schwarber, Taylor bounced all over the field for the Dodgers. In Chicago, he’d be the everyday second baseman, but to know he could spell just about any position on the diamond gives him added value to a team that likes to rest its stars. In addition to adding a second (and much-needed) quality bat in the off-season, his skillset, attitude, and pedigree would make him a great fit if someone like Seager or Semien isn’t in the cards for the Sox. The only issue is that he’s a right-handed hitter, something the Sox don’t need.
The lineup with Schwarber and Taylor projects to this:
R Tim Anderson SS
L Kyle Schwarber RF
R Luis Robert CF
R José Abreu 1B
S Yoan Moncada 3B
R Eloy Jimenez LF
S Yasmani Grandal C
R Chris Taylor 2B
R/L Andrew Vaughn/Gavin Sheets DH
Seeing a left-handed hitter atop the White Sox lineup card is a sight for sore eyes; the last time this happened, Yonder Alonso and Nicky Delmonico were on the team. Giving the Sox an advantage against RHP, something they’ve struggled with mightily over the last 3 seasons, is worth the cost of business here as Schwarber would also cost a lot less than Seager.
Anderson remains atop the order, this time backed by Schwarber — who was very advantageous against pitchers batting at the top of the order for Washington and Boston. Robert, the best true hitter in the lineup, hits third here, with Abreu hitting cleanup and Moncada manning his most successful lineup position of the 2021 season: fifth. Eloy and Grandal can rotate hitting sixth and seventh based on matchup (and momentum), while Taylor and the projected DH committee give the Sox a lot of pop late in the order.
There’s also room to play with this roster: Schwarber, Robert, Grandal, Moncada, Jimenez, and Taylor can (and have) hit just about everywhere in the lineup. If Abreu is slumping, Schwarber and Yaz can slot in the middle of the order. If Anderson and Jimenez need to rest their legs, Robert, Vaughn, and Sheets, can move up as necessary. Just about anyone in the lineup can hit just about anywhere and it wouldn’t make much difference. And if they’re given the chance to play together for 2-3 years, they’ll be one of the hardest teams in the league to get 27 outs against.
The Likely Outcome: Adam Duvall & Eduardo Escobar
Reality dictates that the aforementioned dream scenarios will never come to pass. The Sox likely won’t be able to afford Castellanos or Seager (or at least will actively choose not afford them), and Jerry will probably find some reason to talk himself out of paying both Schwarber and Taylor. From there, the rest of the field is either too old or too much of a lateral move to what they already have in house to pull the trigger.
But Duvall and Escobar would provide veteran leadership, a lot of power, and pretty solid defense — and for pretty cheap. Their inability to sustain high on-base numbers limits both of their negotiating position, so it makes lots of sense. If the Braves don’t make a decision on Duvall by the deadline on December 2, Hahn will not pass up on someone to man the outfield while Vaughn and Sheets develop. And Escobar would probably love to come play in Chicago now that they’re favorites to win the division for the foreseeable future.
Duvall would actually be a great fit for the Sox. Meanwhile, Escobar would be, well ... better than nothing. Plus, being a switch hitter is a nice feature to have. The only hope will become making sure La Russa doesn’t bat him fifth in the order.
Assuming he isn’t that incompetent, here’s what the lineup card would project to look like:
R Tim Anderson SS
S Yoán Moncada 3B
R Luis Robert CF
R José Abreu 1B
R Eloy Jiménez LF
S Yasmani Grandal C
R Adam Duvall RF
R/L Andrew Vaughn/Gavin Sheets DH
S Eduardo Escobar 2B
In this instance, Moncada retains his spot hitting second and Robert remains in the three-hole. Abreu and Jiménez bat cleanup and fifth, respectively, while Grandal gets on base for Duvall and the DH rotation. This lets Escobar set the table for the top of the order.
Otherwise, sadly not a whole lot changes from this year to next in this instance, but the Sox wouldn’t need to rely on Leury García to play every day anymore, or Adam Engel to stay healthy. Both could return to their platoon positions and provide the Sox with much-needed depth as they try to repeat as AL Central Champions and push over the edge for a World Series title.
Duvall and Escobar don’t have the same type of impact offensively as many of the other hitters on the market, but the Sox do have enough talent to hope that they can build late-season momentum and be positioned to win their matchups. Chances are, Jerry will make sure his front office sees it the same way.
This outcome would really only be viable if the Sox are able to shore up their pitching woes; Carlos Rodón is sure to pursue a well-deserved pay raise to be a staff ace elsewhere and Dallas Keuchel is going to be lucky to keep his job next season given how poorly he pitched. But most notably, this less expensive route with the position players would leave the door open for the Sox to pursue someone like Marcus Stroman or Robbie Ray to pitch alongside Giolito, Lynn, Cease, and Kopech.
Pins and Needles
Sox fans — and Sox ownership — have a lot to think about over the next few months. There are myriad routes Rick Hahn might be allowed to take. It also wouldn’t be surprising if trades develop sometime over the winter. Players like Whit Merrifield, Jonathan India, Brandon Lowe, and Isiah Kiner-Filefa all fit the payroll wishes for Jerry Reinsdorf and none would require massive prospect capital in exchange. Or perhaps a change of scenery would awaken Gleybar Torres.
Who knows? Maybe Hahn has another miracle up his sleeve and a massive trade package for Juan Soto might materialize ...
A boy can dream.
And of course, there’s the rotation to think about. I imagine Hahn would trade Keuchel to anyone for a bag of peanuts at this point, and despite an impressive turnaround in 2021, Reynaldo López does not seem like a viable solution long-term.
If shoring up the rotation with a star instead of the offense is the goal, fans might be excited for a few months, but they project to have the same postseason issues in 2022 that they faced against Houston in 2021. The offense needs to add depth to be productive against top-tier pitchers, and everyday players with defensive aptitude should be utilized, not utility guys.
All this to say: If the Sox really want to get themselves over the hump, committing to simply filling in these gaps cannot be the only priority. How they go about filling them requires the same level of commitment.