The Future of the Chicago White Sox Just Got Brighter
After securing the first overall pick in the 2026 MLB draft, this week was a major step forward for the Chicago White Sox's rebuild.
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When the calendar turns to July 11, 2026, the Chicago White Sox will be selecting first with the potential to draft a franchise-altering player. A team that already showed progress in their rebuild down the stretch of 2025 is taking more steps forward this offseason.
It has been quite some time since I’ve been able to put pen to paper and talk about the White Sox. There’s no better time to do so than following my time at the MLB Winter Meetings, which included the dream scenario for the White Sox on Tuesday evening.
Chicago entered the MLB Draft Lottery with the highest odds of landing the first overall pick at a tick above 27%. While that may seem high, no team with the sole highest odds has actually won the first pick since the draft lottery started four years ago.
With the last White Sox player to be selected first overall, Harold Baines, representing the team Tuesday at the lottery, it happened.
The Impact Of Winning the Draft Lottery
For the White Sox, this means more than just simply being able to take any player they desire at the start of the amateur draft for a couple of reasons.
First of all, it marks a new point in this rebuild for the organization. The momentum is already with the White Sox in many ways as optimism surrounding the young core grows, and this amplifies the buzz.
The next factor is straightforward: One of the best draft prospects we have seen in this generation will be the heavy favorite to go first overall in July. Roch Cholowsky of UCLA Baseball is the consensus top prospect in this class right now and is viewed as a potential franchise-altering talent.
Amateur Scouting Director Mike Shirley has had Cholowsky on his radar since his prep days.
“We spent a lot of time on him in high school. Felt like he was worthy of being a high-end pick. So I do feel like we know the kid, know the family,” said Shirley.
Everyone is aware of Cholowsky’s potential, which will inevitably lead to buzz about him in Chicago for the next eight months. Think Zion Williamson for New Orleans leading up to the 2019 NBA Draft.
“Roch’s a good player. I do think he’s earned the right to be on that leaderboard. We have a long way to go. He’s gotta continue to refine his skills as players do leading up to the draft. But he’s a great player,” explained Shirley.
The organization is well aware of the hype surrounding Cholowsky and should just about have a front row season ticket at UCLA this spring.
To be clear, a lot can change between now and July, but he will remain the favorite to be taken with this pick, barring anything drastic.
Adding a Superstar Prospect
While the White Sox did take a step forward following their historically bad season in 2024, they still lack a true superstar prospect.
The depth throughout the MLB roster and farm system has ticked up in a big way, but there is still a need for some further development of those in the organization and an influx of star power. Enter Cholowsky.
With that said, the organization will do its due diligence on every top prospect, including the likes of Grady Emerson, AJ Gracia, and Drew Burress. When the time of the draft comes, general manager Chris Getz appears confident in their ability to get the desired player.
“It’s a little more efficient…But with how the draft works, teams can move draft picks around based on pool space,” said Getz when asked about being able to focus on a select few players with that pick. “But when it’s a clear number one, I would say logistically it becomes a lot easier.”
It appears that if the organization is set on a player come July, they will do everything in their power to get the financials finalized.
Whether it be Cholowsky or another prospect, the White Sox will add an elite talent and a premier prospect to their system with the top pick.
Beyond just that pick, winning the lottery will likely result in the White Sox having the largest bonus pool of any team in the MLB Draft. The slot value for the top pick will be higher than the ~$11.075 million slot from the 2025 draft, leading to a total bonus pool that opens a lot of possibilities for the White Sox.
The record signing bonus for any player in the MLB Draft is $9.25 million, which both Chase Burns and Charlie Condon signed for in 2024. Cholowsky will undoubtedly break that record in 2026, but he still should seemingly come in well under the slot value that will stand around $2 million higher than the previous record.
Potentially near a million in savings while picking second in each subsequent round of the draft is a great recipe for Mike Shirley and company next summer.
More Flexibility In the Draft
Selecting the player of their choice and having additional resources to allocate toward the following few rounds creates flexibility for Chicago.
When I asked about maximizing the bonus pool in the second through fourth rounds, Shirley was understandably excited.
“I feel good about that. That’s something we’ve accomplished of late with Grant Taylor and Caleb Bonemer. Let’s continue to build that,” said Shirley.
The White Sox have been able to snag first-round-caliber talents recently by floating players utilizing bonus pool money.
“Maybe there are three pieces you absolutely love that you can stretch your dollar a bit to get. Players want value in their pocket, and if you’ve been given the biggest pool, let’s execute with that,” said Shirley.
For Chicago, this opens a world of possibilities. There’s a real chance Chicago can walk away with Cholowsky and another elite talent at the top of the second round. Potentially even another overslot pick in later rounds.
The MLB Draft Lottery went perfectly for Chicago, and that wasn’t all that happened this week in Orlando.
Chicago White Sox Rule 5 Draft Recap
After striking gold last season with Shane Smith and Mike Vasil in the Rule 5 Draft last year, the hype surrounding the event was higher for Chicago than most.
The White Sox took a very different route this time around by selecting a pair of pitchers who have yet to throw above the High-A level to this point.
Jedixson Paez, 21 years old, was selected with the second-overall pick in the Rule 5 Draft from the Boston Red Sox organization. The right-hander only tossed 19.1 innings in 2025 while dealing with injuries, but had an excellent 2024 season and is viewed a serious upside swing by the organization.
His command and versatile pitch mix stand out for a 21-year-old arm. The fastball is unique and will need to continue to improve, but he features various secondaries with strong command of them, particularly a plus changeup. Paez tossed 96.2 innings in 2024 with 113 strikeouts compared to just 12 walks.
Despite a lack of experience and innings, Chris Getz views Paez as someone who can be developed into an impact player.
“Multiple weapons, a lot of different pitches. Obviously hasn’t pitched at the upper levels. In terms of command and his arsenal, our group was really excited. Long-term, we view him as a real starter for us,” said Getz.
Creativity will be the key with a young arm who is viewed as a starter but is not nearly built up enough to be a full starter right away. It seems that an opener or multi-inning reliever role will likely be the best route to keep Paez on the roster this coming season with the hope of him developing into a starter down the line.
Alexander Alberto, 24 years old, was the 13th and final selection of the major-league portion of the draft. Selected from the Tampa Bay Rays organization, the 6-foot-8 right-hander has the stuff of a big-time bullpen arm.
He is viewed purely as a reliever, given his primarily two-pitch mix and velocity that consistently reaches 100 mph. His cutter in particular is an excellent offering sitting in the upper 90s.
“The guy has big-time stuff. It’s a unique pitch with his cutter…that’s a guy we feel like can be a big arm in the back of the bullpen. He’s got stuff that stacks pretty well against any hitter,” said Getz.
Unlike Paez, Alberto is likely to be utilized in short spurts where he can let his stuff loose. He may actually have a better shot at sticking on the roster, given his role, which may be easier to hide a bit in comparison to Paez.
The offseason continues from here, and the White Sox are still actively engaged on the free-agent market, particularly the offensive side, after adding three arms this week.
While adding an impact player would be excellent, this team is still playing for 2027 and beyond. This week was a huge step forward for an organization confident that they’re building a core more effectively than the previous regime.
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Elijah is the Chief Operating Officer for Just Baseball Media. He manages the operations of the company and oversees the management of our staff. Additionally, he…