Important Dates and Events for Pirates During Winter Meetings
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PITTSBURGH — The Pittsburgh Pirates have their most important few days of the offseason coming up in the Winter Meetings in Orlando, Fla.
The Winter Meetings represent the busiest time of the offseason for MLB teams, as the front office, agents and others all meet in one place and discuss trades and free agents.
Pittsburgh has a big week coming up, where they'll try and make moves, but also other events that will play a role in their future.
MLB Draft Lottery and the Pirates Chances
The MLB Draft Lottery takes place on Dec. 9 at 5:30 p.m. and the Pirates have a good shot at the first overall pick in 2026.
Pittsburgh has the third-best chance of landing the first overall pick in the 2026 MLB Draft at 16.81%. Only the Chicago White Sox at 27.73% and the Minnesota Twins at 22.18% have a better shot than them.
The MLB Draft Lottery is set by the teams with the worst record, with the White Sox and Twins having worse records than the Pirates.
The rest of the teams below the Pirates in the draft lottery include the Baltimore Orioles (9.24%), the Athletics (6.55%), the Atlanta Braves (4.54%), the Tampa Bay Rays (3.03%), the St. Louis Cardinals (2.35%), the Miami Marlins (1.85%), Arizona Diamondbacks (1.51%), Texas Rangers (1.31%), San Francisco Giants (1.01%), Kansas City Royals (0.84%), New York Mets (0.67%) and the Houston Astros (0.34%).
The MLB Draft didn't have a draft lottery until the 2023 MLB Draft, which saw the Pirates win the first-ever inaugural draft lottery.
Pittsburgh used that pick and took right-handed pitcher Paul Skenes out of LSU, signing him to a record $9.2 million bonus. That pick worked out well, as Skenes won National League Rookie of the Year in 2024 and then the NL Cy Young Award in 2025.
The Pirates didn't win the draft lottery in 2024, but did take shortstop Konnor Griffin with the ninth overall pick out of Jackson Preparatory School in Jackson, Miss. Griffin is the top prospect in baseball and could join the Pirates' Opening Day Roster for 2026.
Pittsburgh did win the draft lottery in 2025, taking right-handed pitcher Seth Hernandez out of Corona Hills High School in Corona, Calif with the sixth overall pick.
If the Pirates do win the Draft Lottery, getting one of the top six picks, then they won't get a pick higher than 10th in the 2027 MLB Draft, but a top-three pick would absolutely be worth it.
Rule 5 Draft and what the Pirates Could Do
The Rule 5 Draft takes place a day after the Draft Lottery on Dec. 10 at 2:00 p.m. Its main purpose is to prevent teams from stockpiling young talent in their minor leagues
Players that are eligible for the Rule 5 Draft are those that aren't on the 40-man roster and were either 18 or younger on June 5 when they signed, and this serving as the fifth Rule 5 draft afterwards, or 19 or older on June 5 when they signed and this serving as their fourth Rule 5 draft following.
If an MLB team selects a player from the Rule 5 Draft, they have to keep that player on the MLB roster the entire season and can't send them down to the minor leagues.
Players that are selected also must spend at least 90 days on the roster that season and if they don't meet that threshold, due to time on the injured list, they must spend those remaining days on the MLB roster the next season.
If a team trades a player they selected in the Rule 5 Draft, that team taking the player still has them under the same restrictions.
The Pirates protected six players from the Rule 5 Draft ahead of the deadline on Nov. 18 in outfielder Esmerlyn Valdez, infielder Jack Brannigan, left-handed pitcher Tyler Samaniego, and right-handed pitchers Wilber Dotel, Antwone Kelly and Brandan Bidois.
Pittsburgh has 33 players in its minor league system available for other teams to take in the Rule 5 Draft.
Two prospects that teams might consider include catcher Omar Alfonzo and left-handed pitcher Anthony Solometo, who MLB Pipeline ranks 20th and 26th in the Pirates farm system.
The Pirates have one open spot on their 40-man roster, which they could use to take a player in the Rule 5 Draft.
One of the Pirates' best ever players came from the Rule 5 Draft, taking Hall of Fame right fielderRoberto Clemente on Nov. 22, 1954 from the Brooklyn Dodgers.
Trades and Free Agents with Pirates Links
The Pirates already made one big trade this offseason, as they sent right-handed starting pitcher Johan Oviedo, left-handed relief pitcher Samaniego and catcher Adonys Guzman to the Boston Red Sox for top 100 outfield prospect Jhostynxon Garcia and right-handed pitching prospect Jesus Travieso on Dec. 4.
Pittsburgh is nowhere near done with its moves, and the Pirates have links with numerous free agents and players on the trade block.
Some of the names that the Pirates are looking at in free agency include NL MVP finalist Kyle Schwarber and catcher J.T. Realmuto of the Philadelphia Phillies, plus San Diego Padres designated hitter Ryan O'Hearn, Seattle Mariners second baseman Jorge Polanco and a pair of Japanese superstars in Kazuma Okamoto and Munetaka Murakami.
The Pirates have also reportedly looked at players in trades, including left-handed hitters from the Cardinals in Alec Burleson, Brendan Donovan, Lars Nootbaar and Nolan Gorman.
Pittsburgh is also looking at left-handed hitting second basemen in trades like Jeff McNeil of the New York Mets and Brandon Lowe of the Tampa Bay Rays, plus Phillies outfielder Nick Castellanos.
The Pirates may not make any free agent signings or trades during Winter Meetings, which would come as quite surprising, but at the very least, they'll get things moving with agents and other front offices.
Dominic writes for Pittsburgh Pirates On SI, Pittsburgh Panthers Pn SI and also, Pittsburgh Steelers On SI. A Pittsburgh native, Dominic grew up watching Pittsburgh Sports and wrote for The Pitt News as an undergraduate at the University of Pittsburgh, covering Pitt Athletics. He would write for Pittsburgh Sports Now after college and has years of experience covering sports across Pittsburgh.