Today, the MLB Winter Meetings begin in Orlando at Signia by Hilton, which is conveniently located between Disney's Pop Century Resort and Disney's Caribbean Beach Resort, but also not too far from Disney's Art and Animation Resort as well as Disney's Riviera Resort. Disney's Saratoga Springs Resort & Spa and Disney's Yacht Club Resort are accessible via rideshare.
On a personal level, my first Winter Meetings were at some Disney-related property in Orlando back in 2017. The occasional glimpse of beleaguered parents trying to coordinate their children into the implausible itinerary of their overpriced vacation still signals that it's time to go to work, it's time to have transactional conversations with relative strangers.
But what will we be discussing?
Jeff Kent was elected into the Hall of Fame via the Classic Baseball Era Committee Sunday night. The White Sox didn't have anybody involved in this round, which is for the better, but it is something that always happens on the first evening before the Winter Meetings officially begin, but just as everyone is arriving and remembering how to turn their laptops on. Remember Dick Allen? I wrote about him this time a year ago instead of making a bunch of jokes in a preview.
Are there any specific events that involve the White Sox?
The MLB draft lottery is on Tuesday at 4:30 p.m. CT. While losing 101 games last year seemed like a significant improvement, it still was a hell of a lot, and the league -- in terms of the CBA -- officially feels sorry for the White Sox, who have a 27.73 percent chance of landing the first overall pick.
In a rematch of the battle for Justin Ishbia's favor, the Twins have the second-best odds of landing the first pick at 22.18 percent. Rick Hahn will be a panelist on the MLB Network broadcast of the event, so no matter the result, the emotions will be complicated.
Continuing the theme of CBA-mandated benefits distributed based on need, the White Sox have the second overall pick in the Rule 5 draft on Wednesday at 1 p.m. CT, where they'll be hunting for their opening day starter they have recent demonstrated history of identifying more significant contributors than we had come to associate with the event, along with plenty of room on the 40-man roster and depth chart to add arms.
Don't forget that the Sox also have the second pick in the minor league phase of the Rule 5, a stage that has brought the likes of Yermín Mercedes and Omar Narváez into the organization in past years. You don't deserve to gawk over my Shane Smith if you're not ready to obsess over my Joseph Yabbour.
When do White Sox people talk?
Will Venable's turn in the mandated manager availabilities comes on Monday afternoon, and will shortly be followed by Chris Getz's daily scrums with local media. The last of Getz's scrums usually happens immediately after the the major league phase of the Rule 5 draft, unless he does something to futz with the schedule again like complete a blockbuster trade right as the draft is starting.
If the White Sox pull off a coup in the draft lottery, it's easy to imagine a few deliriously happy team officials giving on-record quotes.
What's there to even talk about?
MLB, and certainly its television arm, is desperate to make the Winter Meetings an entertainment event where things actually happen, even if part of players having say in the course of their careers involves not acceding to arbitrary deadlines for when they sign life-altering contracts.
In the White Sox's case, where the number of outlets dedicating resources for an offseason trip into the heart of Disney-dom is usually at threat of dwindling, they do have a number of easy batting practice fastball to throw to traveling reporters looking to write something that justifies the expense.
Two weeks after Sox Machine confirmed that José Leger will be the first base coach, the team has yet to announce their full coaching staff, or reveal if there are still unreported hirings to announce. They waited until the Winter Meetings to finalize Venable's cabinet last year, and could very well do the same thing once again. It's only been a few days since word got out that the Sox agreed to terms on a two-year deal with left-hander Anthony Kay, but they wouldn't even be the first team this year to stall out their introduction of a free-agent addition to the Winter Meetings.
It might be a study in contrasts if the White Sox introduce Kay at the same spot in the media workroom as the Blue Jays are going to hold a presser for Dylan Cease on Tuesday, but it would get them out of lugging around that portable White Sox background they use for scrums. Or they could just do it on Zoom. Everyone loves relegating their work interactions to Zoom.
Yeah, but will the Sox really do anything?
Technically, it's very possible.
At last check, there was nothing imminent cooking with Luis Robert Jr.'s trade market, and it remains something closer to a true tossup if he stays put through the winter. Optimistically, Cedric Mullins signing with the Tampa Bay Rays pulled one of the clear few center field options off the board in free agency. Pessimistically, if the Pirates plan on giving newly acquired Jhostynxon García a real go in center field, then another potential suitor also just dropped out.
Last year, the White Sox signed Mike Tauchman during the Winter Meetings, and already had Austin Slater in tow by then, both on one-year contracts that were largely distinguished simply by being guaranteed major league offers. Which is to say that at least some of the team's shopping will be conducted at a level of the market that can jostle loose at any time. To put it in other words, the Sox and Kay didn't need to wait for Framber Valdez to set the market in order to figure out fair value.
A pursuit of Ryan O'Hearn might require some waiting out to see how his market develops among contenders, but forecasts of a slow winter meetings might not necessarily impede everything the Sox are trying to do this weekend.
This sounds potentially underwhelming
Can’t deny that entirely. We’re certainly hoping there will be some sort of signing, trade or development worthy of having all three Sox Machine staffers in the same place for one of the half dozen times it happens all year. Some years the Garrett Crochet trade serves as a the stunning climax to three days of negotiations, some years you spend more hours than you anticipated diving into Nomar Mazara’s swing mechanics.
But every Winter Meetings is a rare opportunity to interface with the decision makers in the White Sox baseball operations department in a relaxed environment, ripe for big picture questions about where all this is going. And the collection of a lot of the movers, shakers, or simply big talkers of the baseball world in one place gives Sox Machine the opportunity to better understand this unique little team’s place in this unique little industry. The insights from which will not just enrich the solid block of articles and podcast that come out of this week, but in the months and years ahead.
