What to watch at Winter Meetings: Draft Lottery, Rule 5 and more
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It’s time for the Winter Meetings to set Hot Stove season aflame.
This weekend, the baseball world focuses its offseason gaze on Orlando as the Winter Meetings arrive in the Sunshine State on Sunday.
While the focus of the Winter Meetings is usually on the Major League happenings, there will be plenty for followers of prospects and farm systems to track at this year’s meetings, as well as serious implications tied to the fourth Draft Lottery.
Here is the MLB Pipeline guide to the 2025 Winter Meetings:
Trades
Last year, the Red Sox swung a huge prospect-laden deal to land Garrett Crochet from the White Sox, kickstarting the trade market after Juan Soto and Max Fried signed big deals in free agency.
This year, the biggest name popping up in trade rumors is Tigers ace Tarik Skubal, with the baseball world wondering if Detroit might look to deal the two-time American League Cy Young Award winner one year before he’s set to hit free agency. Byron Buxton, MacKenzie Gore, Nick Castellanos are some other names being mentioned in potential trade buzz.
As Jim Callis and Jonathan Mayo discussed on the latest MLB Pipeline Podcast, the Dodgers, Mets, Mariners and Reds are a few of the many teams that have the prospects to swing big deals this year. A pair of one-for-one deals sparked the Hot Stove: the Orioles acquired Taylor Ward from the Angels for Grayson Rodriguez, while the Rangers and Mets swapped Marcus Semien and Brandon Nimmo.
The trade market continued to percolate as the Pirates acquired outfielder Jhostynxon Garcia, the No. 85 prospect in the game per MLB Pipeline, and right-hander Jesus Travieso from the Red Sox in exchange for Johan Oviedo, Tyler Samaniego and Adonys Guzman.
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Draft Lottery
Cue the pingpong balls. The fourth Draft Lottery will take place Tuesday at 5:30 p.m. ET. It will be broadcast on MLB Network and streamed on MLB.com. The lottery determines the order of the top six picks of the 2026 Draft, giving it enormous implications for all 15 eligible teams.
Though the lottery is still only a few years old, teams that do well in the process are already reaping huge benefits. The Pirates snagged the top pick in the first lottery and used it to select Paul Skenes, the reigning National League Cy Young Award winner. Six of MLB’s Top 100 prospects are recent lottery picks: JJ Wetherholt (No. 5), Max Clark (No. 8), Walker Jenkins (No. 10), Eli Willits (No. 15), Travis Bazzana (No. 17) and Ethan Holliday (No. 19).
The White Sox have the best odds of getting the No. 1 overall slot this year, at 27.73 percent. The Twins, Pirates, Orioles, A’s and Braves round out the top six. Neither the Rockies, Angels nor Nationals are eligible for this year’s lottery. They can pick no earlier than 10th, 11th and 12th in the 2026 Draft as a result.
Here is a closer look at how the 2026 Draft order is shaping up.
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Rule 5 Draft
This year’s Rule 5 Draft will take place Wednesday at 2 p.m. ET and will be streamed live on MLB.com.
Players signed at age 18 or younger have to be added to a team’s 40-man roster within five seasons, and players signed at 19 or older must be added within four seasons, or else they become eligible for Rule 5 selection by another organization.
Teams must pay $100,000 to select a player in the Major League phase of the Rule 5 Draft, and the player is required to remain on the 26-man roster for the full season. If the selecting team removes him from the roster, the player must first be offered back to his former team for $50,000.
The Rule 5 Draft is always unpredictable. Last year’s was the most active in decades, with teams making 83 total selections, the most since 2004.
The most notable pick in Rule 5 history remains Hall of Fame outfielder Roberto Clemente, while modern success stories include right-hander Shane Smith, reliever Ryan Pressly and outfielder Anthony Santander.
Free agent signings
While trades are more likely to impact prospects directly, free-agent signings can come with prospect and Draft order implications down the line for the signing player’s new and former clubs.
Free agents who received and rejected a qualifying offer come with Draft compensation once they sign. If their previous club doesn’t receive revenue-sharing money and carried a payroll beneath the luxury tax in 2025, then that organization is eligible to receive a compensatory pick after the Competitive Balance Round B after the player signs elsewhere. If the club exceeded the luxury tax and loses a qualifying free agent, their pick comes after Round 4. If the club is a revenue-sharing recipient and the player signs for at least $50 million, then the compensation pick is between Round 1 and Competitive Balance Round A. If the deal is for less than $50 million, the pick comes after the completion of Competitive Balance Round B.
This offseason, four of the 13 players offered qualifying offers accepted them, a record number. Those who declined: Dylan Cease, Kyle Schwarber, Ranger Suarez, Kyle Tucker, Framber Valdez, Bo Bichette, Edwin Díaz, Zac Gallen and Michael King.
Thus far, Cease, who reportedly inked a seven-year deal with the Blue Jays, is the only player to reject a qualifying offer and sign with a new team this winter. The Padres will receive a CBA pick after the completion of Round 4 as compensation. Additionally, the Phillies, Cubs, Astros, Blue Jays, Mets and D-backs stand to receive Draft compensation unless they re-sign their top-ticket free agents.