Pirates Winter Meetings 2024: Every key update about free agency, trade rumors

The 2024 MLB Winter Meetings kicked off Sunday in Dallas, marking the start of the busiest part of baseball's offseason calendar. From trades to free agent signings to Hall of Fame votes, it's sure to be an action-packed event, and the Pittsburgh Pirates will be in the middle of it all.

National League Rookie of the Year Paul Skenes' historic 2024 season has put some pressure on general manager Ben Cherington and the Pirates' front office to step up and make some moves that will get this team closer to contending, and the Winter Meetings will be a perfect opportunity to start taking action. Will they answer the bell?

Here's everything Pirates fans need to know about the annual event and how it could affect their team in 2025.

What are Major League Baseball's Winter Meetings?

MLB executives, front office representatives from all 30 clubs, countless players and their agents gather at the event once a year and meet for four days to negotiate contracts and trades. The Rule 5 Draft, MLB Draft Lottery and Classic Baseball Era vote for the Hall of Fame also occur during the Winter Meetings.

This year's festivities will take place in Dallas at the Hilton Anatole Hotel. The city last hosted the Winter Meetings nearly two decades ago, in 2005.

Pirates at MLB Winter Meetings: Dave Parker Hall of Fame vote, MLB Draft Lottery, Rule 5 Draft

Pirates Hall of Fame member Dave Parker is on the ballot for Cooperstown again, marking his fourth fourth time on a Classic Baseball Era Committee ballot. The results of the vote will be announced Sunday at 7:30 ET on MLB Network.

UPDATE: Parker was elected, and will be enshrined in Cooperstown next July. Beyond well deserved.

The MLB Draft Lottery will occur on Tuesday, and the Pirates have a 5.31% chance (the sixth-best odds) at the first overall pick this time. The only other time they have landed the first overall pick since the Draft Lottery was introduced was two years ago, when they selected Skenes.

The Pirates will have the eighth overall selection in this year's Rule 5 Draft, which will be held on Wednesday. They also have open spots on their 40-man roster, which makes them eligible to make a selection if they choose.

Pirates Rumors: Most notable 2024 Winter Meetings speculation

The Pirates' biggest needs this offseason are impact bats and corner outfielders. They non-tendered Connor Joe and Bryan De La Cruz, lost Edward Olivares to free agency and finished 25th in the Majors with 160 home runs last year. Pittsburgh needs to bring in at least one corner outfielder (preferably one with some pop in his bat) to deepen a group that currently consists of Jack Suwinski – who is coming off a terrible season – and a handful of rookies and career minor leaguers who are, at best, depth options in the outfield.

There's also the matter of first base; Bryan Reynolds started working out at the position last season, but it's still unclear whether the Pirates will pursue internal options or look to acquire a first baseman via trade or free agency.

The Pirates are in a position of power here, should they choose to accept it. They have the one thing that every team wants: pitching, and lots of it. Outside of the big three (Skenes, Mitch Keller and Jared Jones) and likely top pitching prospect Bubba Chandler, every other arm should be on the table for Pittsburgh to dangle as trade bait; this includes elite-level prospects and Major League back-of-the-rotation arms like Bailey Falter and Luis Ortiz.

Will this finally be the year that Cherington deals from the Pirates' pitching depth to add some offense? Stay tuned for updates from Rum Bunter as the news starts rolling in from the Winter Meetings.

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