The Chicago White Sox arrived in Orlando without the expectations of a splashy offseason headliner, yet left the 2025 MLB Winter Meetings with a clear opportunity to accelerate their timeline without compromising the foundation of the rebuild. While the week did not feature a marquee free-agent signing or headline trade, it may ultimately be remembered as the point where the organization positioned itself for sustainable success.
Winning the No. 1 overall pick in the 2026 MLB Draft immediately altered the White Sox’s long-term outlook, not only by granting access to a potential franchise-altering talent, but by unlocking bonus pool flexibility that can reshape the entire draft class. Coupled with an upside-driven Rule 5 Draft approach and the official addition of Anthony Kay, Chicago used the week to expand its range of outcomes rather than chase short-term certainty.
Just as importantly, the meetings offered clarity. Through media sessions with Chris Getz and Will Venable, the White Sox outlined a philosophy rooted in developmental patience. At the same time, early connections to the outfield, pitching, and first base markets suggested that Orlando was less about closing deals and more about laying groundwork for moves still to come.
Chicago did not leave the Winter Meetings with a finished roster, but they did leave with a path forward. Chicago’s week in Orlando reshaped the direction of the organization and opened the door for a more accelerated, yet sustainable, next phase.
White Sox land the No. 1 pick in the 2026 MLB Draft
The defining moment of the White Sox’s week in Orlando came on Tuesday night, when Chicago won the 2026 MLB Draft Lottery and secured the #1 overall pick. Entering the lottery with the highest odds at 27.73 percent, the Sox finally broke through in a process that has rarely favored teams at the top since its inception. With Colorado and Washington ineligible for top lottery selections under revenue-sharing rules, the path to the top pick narrowed, creating a cleaner runway for Chicago to capitalize on its lottery position.
The symbolism was fitting. Harold Baines, the last White Sox player selected first overall in 1977, represented the organization on stage as the pick was revealed. For a franchise searching for its next cornerstone, the result felt transformational.
“I can’t understate how big of a deal this is for us.”
Chris Getz joined The Chicago Lead after the White Sox landed the 1st overall pick in the 2026 MLB Draft: pic.twitter.com/VmukVSkxvf
— White Sox on CHSN (@CHSN_WhiteSox) December 10, 2025
Landing the top pick is blueprint-shifting on its own, but the impact goes well beyond simply choosing first. The No. 1 selection will carry a slot value projected around $11.3 million, immediately giving the White Sox one of the largest bonus pools in the draft. That flexibility is critical. Even if Chicago signs the top pick for a record-setting bonus, there is still a realistic path to saving seven figures that can be redistributed later in the draft, particularly at the top of the second round, where the Sox will again pick early.
That financial leverage fundamentally changes how the draft can be approached. Rather than being locked into a single decision, the White Sox can be aggressive across multiple rounds, floating premium draft talent or pushing overslot deals deeper into the class. Mike Shirley and the amateur scouting department have already shown an ability to weaponize bonus pool space in recent drafts, and this year presents their most powerful opportunity yet.
As for the player at the top, UCLA shortstop Roch Cholowsky has emerged as the consensus No. 1 name across the industry. While the organization has been careful not to lock into a single outcome months in advance, both Chris Getz and Shirley acknowledged Cholowsky’s standing and familiarity within the building.
“Roch’s a good player. I do think he’s earned the right to be on that leader board,” Shirley said. “We have a long way to go. He’s got to continue to refine his skills as players do leading up to the draft. But he’s a great player.”
Shirley also noted that the White Sox have tracked Cholowsky dating back to his prep days, adding another layer of comfort with both the talent and the makeup. That long-standing evaluation matters in a draft environment where financial strategy and conviction often intersect.
Mike Shirley via White Sox Zoom
Cholowsky is the top player on the newly minted top 100 draft prospects list at MLB Pipeline. The UCLA shortstop is the top player at Baseball America as well. Getz echoed the organizational advantage that comes with clarity at the top.
“When it’s a clear number one, logistically it becomes a lot easier,” he said, referencing how pool space and negotiations shape draft dynamics.
Whether Cholowsky ultimately becomes the selection or another player forces his way into the conversation, the outcome in Orlando placed the White Sox in control. Chicago has a chance not just to add an elite prospect, but to reshape the entire draft and organization in a way few teams ever can.
Rule 5 Draft Selections and Departures for White Sox
Chicago approached the Rule 5 Draft with a clear willingness to bet on upside. Rather than targeting finished products, the front office leaned into profiles where underlying traits could be further developed within their pitching group. The belief was that if even one arm could become a real contributor, the return could move the organizational needle.
The Chicago White Sox have selected right-handed pitcher Jedixson Paez from the Boston Red Sox organization with the second overall selection in the major-league phase of the 2025 Rule 5 Draft and right-hander Alexander Alberto from the Tampa Bay Rays organization in the second…
— Chicago White Sox (@whitesox) December 10, 2025
Jedixson Paez was selected with the second overall pick. Ranked 15th in the White Sox top 30 prospects by MLB Pipeline, Paez stands out for his ability to throw strikes with a deep mix despite limited experience above High-A. Injuries restricted him to just 19.1 innings in 2025, but his previous workload and track record of elite control kept him firmly on the radar.
Paez works from a lower slot and shows comfort using multiple secondaries to neutralize hitters with his changeup and slider already flashing as reliable weapons. The fastball remains lighter than ideal, yet his ability to command the zone and sequence pitches gives the staff a foundation to build around while carefully managing his workload. Getz noted that he is viewed as a potential starter, but could start the year in a multi-inning, opener/swingman role.
Jedixson Paez selected in the 1st Rd of the R5 draft from the Red Sox. Command pitcher that limits walks, using a + CH and SL to keep hitters off his 94 MPH FB. A non-arm related inj. had him miss most of ’25. Ranked 19th in the Red Sox system, hovering around a 1 WHIP. pic.twitter.com/cofo3OhRY5
— FutureSox (@FutureSox) December 10, 2025
Alexander Alberto represented the opposite end of the spectrum. Ranked 21st in the White Sox system by MLB Pipeline, Alberto brings overwhelming raw stuff that can change the look of a bullpen quickly. The 6-foot-8 righty features a fastball that reaches triple digits and a cutter that arrives only a few ticks slower, creating uncomfortable decisions for hitters in short bursts. His slider adds a third look that keeps bats from sitting on velocity. Drawing comparisons from some evaluators to Emmanuel Clase. Alberto has not pitched above Double A, but the organization views him as a reliever whose arsenal can translate immediately if his strike-throwing continues to improve.
Alexander Alberto, selected in the 2nd Rd of the R5 from Tampa. The 6’8″ RHP is 3p pitcher with a FB that tops out at 100MPH, a Cutter at 97, and a low 90’s SL. He is pretty tough to square on. Alberto had a 1.17 WHIP in almost 50IP mostly in Adv A in ’25. pic.twitter.com/vZopyhHJYM
— FutureSox (@FutureSox) December 10, 2025
Jackson Kelley rounded out the draft as a Triple-A phase selection from the Rangers organization. A 12th-round pick out of Mercer in 2022, Kelley is a submarine right-hander listed at 6-foot-0 and 185 pounds. Injuries delayed his season until the summer, but he finished with 34.1 innings, a 2.10 ERA, and 32 strikeouts. His delivery creates uncomfortable angles that disrupt timing, though command remains a reason for concern. The White Sox saw enough deception and movement to believe he could fit into their developmental mix as a situational option.
The cost of these selections came with the loss of Peyton Pallette to Cleveland. Pallette was ranked ninth in the White Sox system by MLB Pipeline entering 2024, and many evaluators viewed him as one of the more advanced relief options available. His departure to a division rival underscores a difficult reality of roster construction. By leaving him unprotected, the front office signaled that he was not part of their immediate bullpen plans. Whether Pallette sticks in Cleveland or eventually circles back will remain a storyline to monitor.
“The Rule 5 Draft, you hope, is a vehicle to acquire the highest level of talent you can.”
Gene Watson on the White Sox Rule 5 Draft process pic.twitter.com/Ugw30G94XH
— CHGO White Sox (@CHGO_WhiteSox) December 10, 2025
These moves reflect an organization prioritizing process over certainty. The White Sox did not chase safety, instead trusting their pitching leadership to identify elements that could be sharpened over time. If Chicago can generate even a portion of the innings they uncovered through the Rule 5 Draft last season, this group could again prove more impactful and leave this front office more than satisfied with the selections.
Anthony Kay Signing Becomes Official
The first confirmed addition of the offseason, left-hander Anthony Kay, officially signed to a two-year deal, and the messaging around it was just as important as the contract itself. Kay confirmed during the Winter Meetings that he is expected to open the season in the rotation, giving Chicago a level of clarity it lacked entering December.
Kay’s return from Japan follows a familiar blueprint for the front office. Chicago acted early on a pitcher they had tracked closely, prioritizing opportunity and role security over waiting for the market to develop. In Kay’s case, the guarantee of a rotation spot played a central role in his decision to leave NPB, even with competitive offers to remain overseas. The Sox identified him as a starter, not a swing arm, and moved quickly to secure him before prices rose.
The Chicago White Sox have agreed to terms with left-handed pitcher Anthony Kay on a two-year, $12-million contract, which includes a mutual option for the 2028 season. pic.twitter.com/j6tfR68uyS
— Chicago White Sox (@whitesox) December 9, 2025
The mechanical and mental adjustments he made overseas helped stabilize his delivery and allowed his stuff to play more consistently from start to start.
Just as importantly, the signing does not appear to be the end of Chicago’s pitching plans. Comments from Chris Getz throughout the week suggested that adding another arm remains likely, whether through free agency or internal competition. Kay’s deal stabilizes the floor while keeping flexibility intact. If his performance mirrors what he showed in Japan, he becomes either a dependable rotation piece or a movable asset at the deadline. If not, the commitment remains modest enough to avoid blocking future plans.
The Kay signing set the tone for how the White Sox approached the Winter Meetings. It addressed an immediate need, reinforced confidence in their pitching infrastructure, and hinted that more additions could follow as the offseason continues.
What the White Sox Are Signaling About 2026
Beyond transactions and rumors, the most important takeaway from the Winter Meetings came from the consistency of the message delivered by the White Sox front office. Chicago used its time in Orlando to reinforce a long-term vision centered on development and measured roster construction rather than short-term acceleration for its own sake.
Chris Getz repeatedly emphasized that the organization remains focused on the group of players closest to the major leagues and the importance of letting that core establish itself organically. “There’s a lot of players on this team and close to the big leagues that’s going to be part of the team that is going to contend for the division,” Getz said. “We don’t want to get ahead of ourselves, and we’re going to continue to make good decisions.”
That framing aligns with how the White Sox have approached nearly every decision since the deadline, prioritizing process over urgency. Health and development were recurring themes, particularly when discussing the pitching pipeline. Noah Schultz’s offseason progress drew positive reviews from multiple corners of the organization.
Scott Merkin reported that Schultz is “doing great” and that the club anticipates him being “full go in Spring Training,” while later adding that the left-hander’s work at the Boras Sports Training Institute in Miami has drawn strong internal feedback. The organization’s tone suggested confidence with Schultz remaining a cornerstone piece whose long-term outlook outweighs any short-term timeline pressure.
That same restraint showed up in conversations about prospect promotions. When asked about Braden Montgomery’s chances of contributing in 2026, Getz struck a measured tone. “We’re always open-minded,” he said. “But with that being said, I see Braden getting into the mix for being on the major-league club next year. I don’t anticipate that happening out of spring training.”
The comment reinforced the idea that opportunity will be earned rather than forced, even for high-profile talent. Roster usage under Will Venable also came into clearer focus as the meetings progressed. Elijah Evans outlined that the young core will continue to receive priority playing time, with flexibility built into nearly every position group. Particularly, on the pitching side, rotation spots are expected to be competitive, though the club does not anticipate rushing prospects into Opening Day roles, even if internal options exist.
Some #WhiteSox thoughts with two days left at the MLB Winter Meetings:
– Young core remains the clear focus. Getting player time for those deemed part of the future will remain the priority this season.
– Kyle Teel and Edgar Quero are expected to split time at catcher.…
— Elijah Evans (@ElijahEv8) December 9, 2025
Bullpen construction offered another example of the White Sox’s broader philosophy. Getz clarified that the club is not locked into pursuing a traditional closer, instead focusing on adding arms capable of handling leverage in various roles. “We’re looking to help our bullpen,” he said, noting that experience matters but flexibility remains key.
Taken together, the message was consistent across every conversation. The White Sox are positioning themselves for growth in 2026, but they are unwilling to sacrifice development in the name of speed. Chicago is committed to a controlled build where progress is intentional and not reactive.
Winter Meetings Notes: Market Signals and Areas of Intent
Chris Getz did not leave Orlando with a wave of finished deals. The week still produced a clear read on where the front office is active. The overlap with division rivals and clubs trying to win now mattered. It also hinted that pricing will shape the Sox path as much as need.
Luis Robert was linked to the #Padres by @MLBBruceLevine today. #WhiteSox have also been linked to starting pitcher Dustin May, reliever Pete Fairbanks and hitters Mike Tauchman, Ryan O’Hearn and Jake Meyers.
— James Fox (@JamesFox917) December 9, 2025
The outfield market moved quickly. That mid-tier group kept getting thinner as teams acted. Kansas City stayed aggressive and eventually filled one of its needs by landing Lane Thomas. Atlanta signing Mike Yastrzemski removed another fit from the board. Those moves reinforced why Chicago may be forced to choose between paying for a known quantity or pivoting to a buy-low type. Austin Hays still fits the realistic profile if the price holds.
Jake Meyers remains the controllable trade option if the Sox want defense and certainty in center field depth if somebody like Luis Robert Jr. is traded. Somebody along the lines of a profile like a JJ Bleday-type reads as the lower-cost rebound candidate who could benefit from a new environment. Mike Tauchman also remains a name to monitor if the market pushes Chicago toward familiarity and shorter-term value. FutureSox has learned that the club has some level of interest in Michael Conforto as well.
The clearest catcher signal was not that Kyle Teel is available. It was that teams are checking anyway. Boston’s interest in a reunion with Teel has been mentioned but the practical path is difficult. Chicago would need a massive return to revisit a deal that already reshaped both organizations. The more realistic version of this storyline centers on Edgar Quero. The Sox have at least explored that lane. The motivation is roster balance rather than a rush to move him. If they trade from that depth it will be because someone meets a high asking price.
Bullpen chatter followed the same pattern as the outfield market. The top of the closer tier came off the board fast. Robert Suarez landing in Atlanta and Edwin Diaz coming off the market created more urgency for the next tier. In that context the Fairbanks connection stands out. Mutual interest is a fair way to frame it. The question is cost and comfort with the medical side. It also fits what Getz has signaled publicly. The goal is not necessarily a labeled closer. The goal is adding someone who can pitch leverage and make the late innings shorter.
Per @scottmerkin, Sox are interested in Pete Fairbanks.
Fairbanks has the 3rd steepest arm angle for a righty in the majors.
His fastball-slider combo is elite. Started throwing a new cutter in 2025 to absurd success.
graph: @tjstats pic.twitter.com/8M88G0Nfzv
— Sean Anderson (@Sean_W_Anderson) December 9, 2025
The same money theme shows up in first base. O’Hearn fits what Chicago is missing. Mutual interest is reasonable to report here, too. The challenge is price. The Sox spending lane is still unclear. Minnesota is circling that mid-tier. Pittsburgh has also signaled it wants to spend after missing on higher-end targets. If those clubs push the number up, Chicago may need to decide whether to stretch or pivot to a different bat tier. Guys like Josh Bell or Rhys Hoskins could then come into focus.
Starting pitching remains active behind the scenes. The expectation is that more arms are still coming to create real competition in camp. Dustin May has been described as on the radar. Some evaluators see him as a potential late-inning fit. That idea fits Chicago’s preference for flexible pitchers, and it matches how they have discussed the staff. It is also consistent with the bigger picture. They want more ways to cover innings.
Luis Robert Jr trade noise lingered in the background. The Mets and Padres surfaced as fits. The New York angle is complicated by how salary offset conversations would work in practice. The on field context is important too. Robert’s second half rebound reminded the league what the player can be when the approach stabilizes. That is why the Sox do not need to force a move. If they trade him it has to reshape the long view.
The Winter Meetings felt like groundwork. Chicago showed activity across the same buckets all week. They are looking at an outfielder. They are looking at leverage relief. They are still open to another veteran arm. They are monitoring the left handed power market. The biggest unknown is how far they can push financially. That will decide whether the next move is a true market win or a calculated pivot to value.
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