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.