
As the Chicago White Sox look to compete for their first playoff birth in over a decade, it appears their rebuild is over as most of their top prospects will all be in Chicago within the next year. The front office has put manager Rick Renteria in a position of sustained success, so let’s see where they could be in 5 years.
WHO WILL STILL BE HERE?
The White Sox are well-known for locking up their young players early in their careers, allowing the team to get the players for an extended time, while giving the players more guarantees. As of right now, the players that are under contract until 2025 and beyond are Yoan Moncada (’25), Dylan Cease (’25), Danny Mendick (’25), Eloy Jimenez (’26), Aaron Bummer (’26), Jimmy Cordero (’26), and Luis Robert (’27). Most of those players should be on the Opening Day roster in 2025, as the White Sox are hoping to be in playoff contention by then.
There are many players that the White Sox should look to extend, whose contracts expire between 2021 through 2024. Carlos Rodon becomes a free agent after the 2021 season, and if he shows that he can stay healthy and be a constant piece in the rotation over the next two seasons, the Sox could look to extend him further, but it might be difficult as he is represented by Scott Boras. Pitchers Lucas Giolito and Reynaldo Lopez both are under contract through 2023. Giolito is a candidate to be extended soon, due mostly in part to his breakout 2019 season. Tim Anderson and Michael Kopech will be a part of the team through 2024, and both players could be extended within the next couple of years, mostly to see how Anderson can perform following his best season yet after winning the Batting Title in 2019, and how Kopech responds after undergoing Tommy John surgery in 2018 and recovering all of 2019. Being able to lock down those players will be crucial for the White Sox future success, but a lot can happen over the next 5 years, so only time will tell.
WHO WILL BE GONE?
The obvious players that will not be on the team in 5 years will be Edwin Encarnacion, Gio Gonzalez, James McCann, and Steve Cishek. Encarnacion and Gonzalez will be 42 and 38 years old respectively, and probably won’t be on any roster by then. The players that I would list as ‘questionable’ would be Jose Abreu, Carlos Rodon, Yasmani Grandal, and Dallas Keuchel.
Although Jose Abreu is a fan-favorite and a leader in the clubhouse, he has been steadily declining recently, and to give him the 3 year extension that he got this off-season was questioned by many fans. At 38 years old in 2025, it is guaranteed that he will not be the first basemen, but there may be a DH position if he can maintain his productivity at the plate, but I believe it’s a long shot.
The White Sox made the first splash in free agency this off-season by signing Yasmani Grandal, who is considered to be a top-2 catcher in the league by many people. Under contract through 2023, it truly is a question on whether he will be on the team still, as he will be 36 years old in 2025.
Dallas Keuchel, another addition this off-season, will be in Chicago through 2023, and will be 37 by the time 2025 rolls around, which is old for a starting pitcher. In my opinion, Keuchel will be around through this current contract, and they will mutually part ways when it expires.
THE LINEUP
Catcher:
Zack Collins (2019: AAA/MLB or Seby Zavala (2019: AAA/MLB)
Both players are likely to spend most of their 2020 season on the ‘taxi squad,’ as Grandal and McCann will be splitting the time behind the plate in Chicago. Both players could be used as trade pieces within the next couple of years, but for now, they are the only players in the organization that I could see behind the plate in 2025. Collins is only 25 and Zavala is only 26 years old, so they should be more polished and near their prime in 2025.
First Base:
Andrew Vaughn (2019: ROK/A/A+)
Andrew Vaughn might be the most polished and MLB-ready prospect the Sox have had by the time he gets to the majors. Expect a late-season call-up, or a debut early in 2021. I think the White Sox let Edwin Encarnacion walk after this season, Jose Abreu makes the shift to DH, and that clears up a spot at 1B for Andrew Vaughn. Vaughn has drawn comparisons to Paul Goldschmidt and Anthony Rizzo, as he works his way through the minor leagues.
Second Base:
Nick Madrigal (2019: A+/AA/AAA)
The starting position at second base is waiting for Nick Madrigal when the White Sox deem him ready (or when they achieve his extra year of control through service manipulation). Madrigal is expected to be a high contact, low power player, and almost never strikes out. Madrigal hit .311/.377/.414, with only 4 HR and 55 RBI. In 532 plate appearances, Madrigal only struck out 16 times, good for a K% of about 3%. Defensively, Madrigal won the Minor League Gold Glove for 2B in 2019, with a fielding percentage of .992%. With not much depth at second base behind Madrigal, he is the teams #1 option for the foreseeable future, as his major league service time has not started yet.
Third Base:
Yoan Moncada (2019: MLB)
Yoan Moncada broke out in 2019, hitting .315/.367/.548, 25 HR, 141 wRC+, and 5.7 fWAR, which was good enough for 16th in all of baseball. Moncada also put up a BABIP of .406, which led the league. That suggests that Moncada is probably due to regress a bit, as he put up .325 and .344 in 2017 and 2018, respectively. That suggests that Moncada was ‘luckier’ in 2019, which is not sustainable. Despite his BABIP, Moncada showed an improvement defensively, after making the shift from 2B to 3B, and being able to show that he has the potential to be the star of this team for the foreseeable future after signing an extension keeping him here through 2025, with an option for 2026.
Shortstop:
Tim Anderson (2019: MLB)
Along with Moncada, Tim Anderson had a breakout year in 2019, taking the league by storm. Anderson made his name known across the league for his passion, flair, and of course, the bat flips:

The bat flip, which resulted in him getting hit by the Royals and caused a bench clearing brawl, sparked a conversation early in 2019, and made his name known among most MLB fans. Tim Anderson followed that with .335/.357/..508, 130 wRC+, 3.7 rWAR, and the 2019 MLB Batting Title. Anderson could see regression in 2020, similar to Moncada, due to his high BABIP in 2019. Tim Anderson became one of the game’s new stars in 2019, due to his ‘have fun’ mentality.
Left Field:
Eloy Jimenez (2019: MLB)
Eloy Jimenez made his long-awaited debut in 2019, hitting .267/.315/.513, 31 HR, 79 RBI in 122 games. Jimenez has shown his struggles in the outfield, so placing him at DH in 5 years would not be too far-fetched. Jimenez has made it known that he has continued to work on his defense over the offseason. Jimenez has been one of the top players the White Sox have decided to build around, so it should be a lock that he will be in the lineup in 2025.
Center Field:
Luis Robert (2019: A+/AA/AAA)
Despite his debut getting pushed back due to COVID-19, Luis Robert’s starting spot in CF is still waiting for him. After being signed out of Cuba in 2017, Robert flew through the White Sox minor league system, and signed an extension that would allow him to start the 2020 season in Chicago, and keep him there through 2027. I previously wrote about what to expect from Robert, so for more in-depth analysis, click here.
Right Field:
???
This is one position that is truly a question in 2025, and even as soon as 2021. While they have prospects such as Blake Rutherford (who I wrote about here), Micker Adolfo, Luis Basabe, and Luis Gonzalez, the right field position is not set in stone. While hopefully those prospects can develop into at least one quality outfielder, it is too soon to tell in their respective careers. Nomar Mazara is set to be starting in right field in 2020, and has his final arbitration year in 2021. This was a move made over the offseason that was looked at by many as a low-risk/high-reward, only giving up a mid-tier prospect for him. In the free agency class after this season, players like Mookie Betts, George Springer, Marcell Ozuna are all free agents. While Jerry Reinsdorf has never been one to spend, the team has cap space to make it happen, and if it’s the one thing keeping them from contending for a championship, he could go that route.
STARTING ROTATION
Lucas Giolito (2019: MLB)
Lucas Giolito had a breakout year in 2019, showing that he is the ace of the pitching staff for the foreseeable future. With his contract set to expire after 2023, there is a good chance he is the next player on the team to receive an extension. The front office loves to extend their players and buy out their arbitration years, and they still have room to make this happen.
Michael Kopech (2019: DNP)
Michael Kopech made his debut in 2018, although short, proved many White Sox fans to be optimistic for his future. After undergoing Tommy John surgery after starting 4 games, Kopech is on track to return in 2020 to the rotation. Kopech, who was the second player the White Sox received for Chris Sale, looked to be just as good, if not better, during his Spring Training appearance, throwing 100, 101, 100, and 101 MPH on his first 4 pitches back in Spring Training, showing that his velocity is still where it was. (For more insight on what to expect from Kopech, click here.)
Dylan Cease (2019: AAA/MLB)
Dylan Cease is another ‘flamethrower’ in the White Sox arsenal. Making his debut in 2019, Cease showed glimpses of being a potential middle-rotation piece, and if he can gain more control, his potential only grows, because his ‘stuff’ will always be there. Given an up and down year, Cease ended the season strongly only giving up 1 ER in each of his last 3 starts, and striking out 11 against the Indians in September.
Garrett Crochet/Reynaldo Lopez
In the shortened 2020 MLB Draft, the White Sox selected a pitcher in all 5 rounds, with the focus being on their top 2 picks. Garrett Crochet was selected 11th overall, and looks to be ready for the majors within the next year or two. I wrote about Crochet and what he brings here. “Crochet throws a fastball that was around 95-97 MPH, but touched triple digits last fall and during workouts over the past couple of months, and is looked at as his best pitch. Crochet will fit in with the pitchers such as Michael Kopech and Dylan Cease, who have a similar projection. His secondary pitch is a slider, which sits around 84-86 MPH. His two primary pitches are followed by a change-up, which MLB.com defines as “well above average” and “around 90 mph with deceptive arm speed.” He has also shown a curveball, which Prospects Live defines as, “More 12-6 drop than you’d expect from a lefty with his arm action and release point. Reluctantly grading the pitch but need more viewings.” With the development of his 4th pitch, Crochet looks to be in the starting rotation, but could also project into the bullpen, only starting in 13 of his 36 games at Tennessee, Crochet would not be a stranger to a role in the bullpen, similar to someone like Andrew Miller.” Should these players live up to their current projections, they could sit in the 3-5 range of the rotation. Reynaldo Lopez was acquired alongside Lucas Giolito and Dane Dunning in the Adam Eaton trade. Lopez’s contract is set to expire after 2023, but he will only be 29 years old. If Lopez is able to bounce back after an underwhelming 2019, he could be a candidate to be extended.
Jared Kelley/Jonathan Stiever/Dane Dunning/Free Agent/Trade
In the second round of the 2020 MLB Draft, the White Sox selected Jared Kelley, who was looked at as a top 15 talent, but once he dropped out of that range, his ability to be signed became a question. The White Sox were able to draft and sign Kelley, due to drafted below slot with their last three picks. Kelley should be on a longer track than Crochet, as he is a prep player and probably won’t see the majors for at least 3 seasons. It is hard to project these players, as we have yet to see them preform in the Minor League yet, and in Kelley’s case, in college.
Jonathan Stiever made his name known among most White Sox fans in 2019, as he made a climb up the organization’s Top-30 prospects, currently sitting at #5, and could see himself in the MLB Top-100 at the midseason rankings. Stiever spent 2019 across Single-A Kannapolis and Advanced-A Winston-Salem, and posted a 3.48 ERA, 1.18 WHIP, 154 K, 27 BB across 145 IP (26 games started). Stiever could see Major League-action in 2021/2022.
Dane Dunning came in as a highly-regarded prospect, but was sidelined with an injury that required Tommy John and sidelined Dunning for the entirety of the 2019 season. Dunning will be on the Summer Camp roster, likely on the ‘taxi squad’ and could see a promotion to Chicago in 2020/2021. Dunning had a very good 2018 season, and looks to pick up where he left off.
If none of the pitching prospects, the White Sox could look to free agency, where younger pitchers such as Trevor Bauer (29), Jose Quintana (31), Noah Syndergaard (27), Blake Snell (27), Tyler Glasnow (26), Chris Sale (31), Jacob deGrom (31), and Walker Buehler (25). Obviously, most of those players will demand a lot of money, and will possibly be extended by their current team. There are also aging veterans, where nobody really knows how healthy and productive they are, or if they are even playing in 2025, such as Clayton Kershaw (32), Max Scherzer (35), Zack Greinke (36), and Justin Verlander (37). Although Jerry Reinsdorf and the White Sox have not been known as ‘big spenders,’ this could be the missing piece for a potential World Series team. Reinsdorf has expressed a desire to “win one last championship before he goes,” and if this is the only thing standing between him and another ring, he could open up the checkbook. The players identified as ‘young,’ will definitely require a long-term deal, and would be difficult to pull off. The older players listed above will be short-term solutions, at the end of their careers. Adding 5 years to their age for the 2025 season, most will be older than 40, and will probably be a shadow of their current-selves. Finding a trade partner is another option due to the prospect pool that the Sox have gathered over the last 4 years. This could be a trade for a ‘rental’ pitcher, who would only have a year or two remaining on their contract, but would also be a cheaper cost in a trade.
IN THE BULLPEN
Aaron Bummer (Closer)
Aaron Bummer burst onto the scene in 2019, making himself the teams most reliable arm in the bullpen. After struggling in his time in AAA-Charlotte and Chicago in 2018, Bummer found success in 2019, which resulted in Bummer receiving a 5 year/$16 million extension, with an option that would take him through the 2026 season. This deal makes Bummer the piece that the Sox intend to build their bullpen around, especially around the mystery of Alex Colome’s future with the team, as his contract expires after the 2020 season.
Zack Burdi
The White Sox selected Zack Burdi in the first-round of the 2016 MLB Draft, but his career has been sidetracked by injuries that have slowed down his progression. The Illinois-native had his 2017 season in Charlotte-AAA cut early due to Tommy John Surgery, which also kept him out of the 2018 season. When he returned in 2019, his season ended in June after a knee-injury. Burdi was drafted with the expectations to be in the bullpen quickly, but as we sit in 2020, he has yet to use any of his Major League service time. Burdi pitched in Spring Training before the season was postponed, and is a candidate to be in the White Sox bullpen in 2020 and beyond.
Jimmy Cordero
In a bullpen that was a revolving door in 2019, Cordero put up impressive numbers in 30 appearances. Putting up a 2.75 ERA, 31 SO, 11 BB, and .972 WHIP in 36 innings. At 26 years old right now, Cordero would be 31 in 2025, which makes him a possible extension-candidate if he succeeds in 2020.
Evan Marshall
Marshall found success in his first year with the White Sox, putting up a 2.49 ERA, 41 SO, 24 BB, 1.303 WHIP, and 1.8 bWAR in 50.2 IP. Marshall will be 30 years old for the 2020 season, and is under control through the 2022 season, and could see himself extended within the next year.
Jace Fry
Jace Fry has been a fixture in the Sox rotation over the past few seasons. Although he hasn’t been ‘lights-out,’ he has put up a 4.38 and 4.75 ERA in 2018 and 2019, respectively. Fry is under control through arbitration through the 2023 season, and will be 26 years old during the 2020 season. Still young, Fry has a chance to impress the front office over the next few seasons so he will be around during the 2025 season.
Ian Hamilton
Hamilton only pitched 16.1 innings before suffering multiple facial fractures, ending his 2019 campaign. Hamilton has shown upside in his minor league career, and is only 25 years old, with multiple years remaining on his contract.
Tyler Johnson
Tyler Johnson was selected in the fifth round of the 2017 MLB Draft. In 2019, Johnson put up a 2.87 ERA, 43 SO, 10 BB, and a .989 WHIP across 31.1 innings in Rookie/A+/AA, and will be on the White Sox Summer Camp squad, and most likely on their ‘taxi squad’ in 2020.
Carson Fulmer/Codi Heuer/Jimmy Lambert
The last spot in the bullpen is left up for debate. Carson Fulmer, who was a former eighth overall pick, has struggled in his time with the White Sox. Making the move from starting pitcher to the bullpen has not been great either for Fulmer. While there is a lot of reason to doubt Fulmer, our own Jordan Lazowski wrote about why he has not given up on Fulmer here. Codi Heuer spent 2019 in A+ and AA in 2019, and has shown promise in the bullpen with a 2.39 ERA in 67.2 innings last season. Jimmy Lambert started in 11 games and pitched 59.1 in Birmingham-AA before undergoing season-ending Tommy John surgery. Lambert, like Tyler Johnson, is on the Summer Camp roster, and will likely spend the season on their ‘taxi squad.’
WHAT DOES 2025 LOOK LIKE FOR THE WHITE SOX?
Rick Hahn has made it known that he expects the team to be competitive and contending for an AL Central division title in 2020, and has preached the idea of sustained success. The White Sox have put themselves in a position to be contending for the foreseeable future, and that includes 2025. The 2025 season should hold World Series hopes for the White Sox, depending on how the players develop.
The infield is pretty much set, and 2/3 of the outfield as well. Questions regarding who will be in the rotation and bullpen are still up in the air, but Rick Hahn has shown that he is not afraid to find answers through the trade market, and this past offseason has shown that they are ready to spend if it means championships, but regardless, it is safe to say that White Sox fans are going to be in for a fun ride over the next 5 seasons.