The first few days of the 2025 MLB Winter Meetings have come and gone, and while there have been very few actual moves made by any of the 30 MLB ballclubs, there are still two days worth of action to come.
Here’s everything to know about the White Sox, including some rumors surrounding some of their current players, as well as some MLB Draft details with the future of this year’s #1 pick still looming.
White Sox to find out 2026 Draft position today
Today marks the fourth occurrence of the MLB Draft Lottery, and for the first time, the White Sox have the best odds – 27% – at the number one overall pick in the draft. Should these odds come to fruition, it would be the first time the White Sox pick first in the draft since they selected Harold Baines in 1977 and just the third time in team history (shoutout to Danny Goodwin in 1971, who was technically the first ever to be selected first overall by the White Sox, but didn’t sign with the team).
As a refresher, here’s how the MLB Draft Lottery actually works:
- Only the first 6 picks are randomized
- Only non-playoff teams are eligible
- Tanking no longer guarantees the top pick because odds are flattened
- Large-market teams cannot receive a top-six pick in back-to-back years
- Small-market teams are capped at two straight lottery appearances
If the White Sox receive a top-six pick this year, the highest they can pick next year is once again 10th overall, as they did last year.
The overwhelming favorite to be the #1 overall pick: UCLA SS Roch Cholowsky, who is considered to be one of the best draft prospects in recent memory. He features a unique combination of speed, power, and defense, and in his sophomore season, he hit .353/.480/.710 with 23 homers in 66 games. He was also strong two years ago as a freshman, hitting .308/.399/.500 across 52 games.
The draft will begin tonight at 4:30 PM CT. Get your popcorn ready.
Red Sox interested in trading for Kyle Teel
According to MassLive.com’s Sean McAdam, the Red Sox are apparently looking at a familiar name to help upgrade the catching position: Kyle Teel. It’s rumored that the Red Sox have at least reached out to the White Sox about Teel, who was drafted by the Red Sox and traded as part of the Garrett Crochet deal. However, nothing appears to be close at this time – and it’s unlikely the White Sox are really entertaining the idea of trading Teel.
This report likely stems from the idea that the White Sox are willing to trade one of their two catchers – Edgar Quero or Kyle Teel – but with a preference to move Quero over Teel based on the on-field results in 2025.
While the sample size was small, Teel appeared to be both further along in his development at the major league level and to possess a higher ceiling than Quero. It remains doubtful that the White Sox will move either catcher, however, with the team likely still wanting to see what another offseason of development looks like for both players, especially given that 2026 looks to be another season focused on growth for the organization.
White Sox make Anthony Kay signing official
Five days ago, reports first surfaced that the White Sox had signed LHP Anthony Kay to make a return to the major leagues after two seasons playing internationally. The White Sox made the move official today.
For a full breakdown of this signing and what Kay brings to the organization, check out a previous article from when the news first broke.
Fairbanks, May drawing interest from White Sox
There haven’t been many free agent names the White Sox have been connected to, but a few are starting to pop up that would address clear positions of need.
According to MLB.com’s Scott Merkin, the White Sox have interested in bringing in reliever Pete Fairbanks, while CHSN’s Chuck Garfien reports that Dustin May is “on the radar” for the White Sox.
Both moves would address near-term deficiencies for a team that is still looking to build on its foundation from 2025. Fairbanks, 31, would represent stability at the closer spot in the bullpen after a year of Venable and the White Sox being willing to play closer-by-committee. Fairbanks has 90 career saves – including at least 23 in each of the last three seasons – and is coming off a 60.1 inning campaign in which he posted a 2.83 ERA and 24.2 K%. To this point, he has spent the majority of his major league career with the Rays and would become a veteran presence for players such as Jordan Leasure, Grant Taylor, and Mike Vasil.
“We’re looking to help our bullpen, and there’s different ways of doing that. I wouldn’t say it’s a set closer, so to speak. It would be nice to get someone who has closer experience, but that doesn’t mean it’s going to be a ninth-inning guy, or even an eighth-inning guy. Someone that can help in higher-leverage situations is something that we’re set out to add.”
– Chris Getz (via MLB.com’s Scott Merkin)
Fairbanks’ unique arm slot would represent a stark difference from your typical bullpen arm, as his 59-degree arm angle is the third-steepest in baseball. His fastball/slider-heavy combination fit right into the White Sox’ typical target arsenal, and he is among the best in the league at missing barrels (93rd percentile Barrel% in 2025) while running his average fastball up to 97 mph.
While some might prefer the White Sox to spend limited funds on non-bullpen pieces, signing Fairbanks would represent not only an ability to lock down close games late for a team that lost 50 games after having the lead at any point and was 16-38 in one-run games, but could also be a legitimate trade piece at the Trade Deadline. As we saw last year, premium bullpen arms with a history of success tend to bring back a quality return at the deadline, and that was something the White Sox missed out on in 2025.
The sticking point will likely be salary – Fairbanks could look to names such as Devin Williams (3/$51M) or Ryan Helsley (2/$28M) as his preferred short-term deal structures. With Edwin Diaz signing with the Dodgers this morning (3/$69M), we have likely seen the ceiling for relievers this offseason. It is unclear just how much the White Sox would be willing to commit to a reliever.
With May, the White Sox could look to add another name to the starting rotation competition with Anthony Kay already in the fold. Once a top prospect with the Los Angeles Dodgers, injuries and/or ineffectiveness have plagued May’s career. After missing the entire 2024 season, the 28-year-old threw over 100 innings for the first time in his career in 2025 and struggled mightily to the tune of a 4.96 ERA. He also struggled with the long ball, giving up 21 in total (1.43 HR/9 and 14.3% HR/FB).
He features a more unique east-west arsenal that is similar to Jonathan Cannon’s (sweeper, sinker, four-seam, and cutter are his four main pitches). The biggest thing that suffered returning from Tommy John Surgery was his fastball velocity – a full 2-3 mph slower on average than before injury. His sweeper and sinker have graded out well above-average, however, and towards the end of the season, he was posting some of his highest velocity readings of the season.
Should the White Sox take a chance on May, it would likely be a relatively cheap deal, with Brian Bannister and new pitching coach Zach Bove believing that they could refine May’s arsenal, perhaps add a serviceable changeup, and bring him back to his previous prospect status.
White Sox connected to OF Jake Meyers in trade talks
The White Sox, much like other teams, have been busy exploring names even if nothing has yet happened (though, shoutout to both Kyle Schwarber and Edwin Diaz signing while this article was being written). The one name on the trade front they’ve been connected to is Astros outfielder Jake Meyers.
Per MLB.com’s Brian McTaggart, the White Sox join the Dodgers, Reds, and Royals as teams interested in Meyers, who has two seasons left of team control.
Meyers, 29, is coming off his strongest season to date, hitting .292/.354/.373 across 104 games while seeing his strikeout rate drop to 17.6% and walk rate rise to 8.1%. However, it’s worth calling out that those numbers came with an inflated .353 BABIP, well above his career average of .307. He has hit as many as 13 home runs in a season previously, though he only hit three in 2025. As a right-handed hitter, he actually had more success against RHP this season, posting a 111 wRC+ against RHP and 93 wRC+ against LHP this season.
His defense has long been his calling card, however, and is more likely the reason teams are interested in trading for him. His 9 Outs Above Average (OAA) ranked in the 95th percentile in 2025, and he was coming off a 2024 campaign in which he posted another 13 OAA in center field.
Meyers would represent some sort of insurance policy in the case that the White Sox do trade Luis Robert in the near future (as has been constantly rumored) – albeit with a much lower offensive ceiling. In practice, Meyers would represent depth in the case that previous acquisition Everson Pereira does not become the impact bat the team hopes he will.
It is rumored to be starting pitching that the Astros seek in return for Meyers.
Other News and Notes
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Featured Image: Scott Merkin (@scottmerkin) / X
