When the Winter Meetings begin on Sunday, most of us will be obsessed with the chatter about trades and free agents. Who are the Orioles in on? Who have they been linked to?
On Monday, we’ll get to meet new Orioles manager Craig Albernaz for the first time as he conducts his media session, and presumably later that afternoon, find out what president of baseball operations Mike Elias thinks are his priorities in the free-agent and trade markets.
But there are other events that will capture Elias’ attention in the four days in Orlando.
Late Tuesday afternoon, the Orioles will learn where they’ll pick in the 2026 draft. They have the fourth-best odds of picking first with a 9.26 percent chance of winning.
Only the Chicago White Sox (27.73 percent), Minnesota Twins (22.18) and Pittsburgh Pirates (16.81) have better odds.
So the Orioles have a chance to win the lottery and the top pick in the draft for the third time in eight years under Elias.
Since the draft began in 1965, 23 of the 30 teams have drafted first at least once. Besides Adley Rutschman (2019) and Jackson Holliday (2022), current Orioles broadcaster Ben McDonald was the overall first in 1989.
While the Twins and Pirates have combined for nine overall top selections, the White Sox, who have lost 223 games in the past two years, had only one No. 1 pick, Easton’s Harold Baines in the 1977 draft.
With their 9.24 percent odds, the Orioles have a better chance to win than the Cleveland Guardians did in 2023. Cleveland (76-86) had a record similar to the Orioles’ last year and had a 2.0 percent chance of winning and did.
This year’s Orioles finished 75-87, the seventh-worst record in baseball.
Teams are prohibited from receiving lottery picks in three consecutive years. That’s why the Colorado Rockies, who picked third and fourth in 2024 and 2025, are ineligible despite losing a franchise-worst 119 games this year.
Teams in larger markets are ineligible to participate in the lottery for consecutive seasons. The Washington Nationals and Los Angeles Angels, who chose first and second, aren’t eligible, either despite having worse records than the Orioles.
The lottery was instituted to prevent tanking.
Should the Orioles win the lottery, or even finish in the top four, they could take another shortstop.
Shortstops head MLB Pipeline’s list of top prospects. UCLA’s Roch Cholowsky, Fort Worth (Texas) Christian’s Grady Emerson, Alabama’s Justin Lebron and Gulliver (Florida) Prep’s Jacob Lombards are the top four, and they’re all shortstops.
When the Orioles last chose first in 2022, there was a debate about who would go first. Outfielders Elijah Green and Druw Jones, infielders Termarr Johnson and Brooks Lee were among those mentioned. Instead, they took Holliday.
The 2022 draft took place just two days after the Orioles concluded a 10-game winning streak that propelled them back into relevance.
While Elias would like another crack at a top pick, a return to the postseason conversation would be preferable.
Rule 5 coming up
The Orioles select seventh in the Rule 5 draft on Wednesday. Their position is more straightforward. They had the seventh-worst record, so they pick seventh.
Until Friday, the Orioles had 39 players on their 40-man roster, making them eligible to take a pick. On Friday, they claimed outfielder Will Robertson off waivers from Pittsburgh and catcher Drew Romo from Colorado. The Orioles haven’t announced the moves and need to move a player off their 40-man roster.
Unless the Orioles enter Wednesday’s draft with an opening on their 40-man roster, they’ll be ineligible to participate in the Rule 5.
Robertson, a 27-year-old left-handed hitter hit .129 with nine RBIs in 27 games with Toronto and the Chicago White Sox this season.
He was claimed by the Pirates from the White Sox on October 13th.
Robertson played in two games against the Orioles in September in Chicago, going hitless in three at-bats.
Romo, a 24-year-old switch-hitting catcher hit .167 with six RBIs in 19 games for the Rockies in 2024 and 2025.
World Baseball Classic
Managers and general managers of World Baseball Classic teams will speak on Tuesday, and there are some familiar names and interesting storylines.
Dean Kremer is set to pitch for Team Israel, and it wouldn’t be a surprise to see Gunnar Henderson play for Team USA, though Kansas City’s Bobby Witt Jr. is already set to play.
Team USA manager Mark DeRosa will be there. Other nations have former Orioles. Canada manager Ernie Whitt, who concluded his career with the Orioles in 1991, Dominican Republic general manager Nelson Cruz, and Mexican general manager Rodrigo López will also be available.
Call for questions: I answer Orioles questions most weekdays. Please send yours to: [email protected].
