The 2024 Winter Meetings in Dallas are set to kick off, bringing together executives from around the league. This typically bustling week of the offseason officially begins on Monday and continues through Thursday, promising a flurry of trades, free agent signings, and other rumors. For the Pittsburgh Pirates, there's a lot on their plate between now and the start of spring training. Under Ben Cherington's leadership, they've had success at previous Winter Meetings and are looking to do so again.

What's Been Done

The Pirates have made several staff additions. Matt Hague has been brought in to replace Andy Haines as the hitting coach. Hague, a former Pirate for two seasons, was the Toronto Blue Jays' assistant hitting coach in 2024. Additionally, Brent Strom, a 76-year-old pitching coach with a long and illustrious career, has joined as an assistant pitching coach under Oscar Marin for the 2025 season. He has worked with notable pitchers like Gerrit Cole and Justin Verlander and guided his teams to the World Series four times, winning it all with the Houston Astros in 2017.In terms of player additions, the Pirates traded with the Cleveland Guardians last month, acquiring right-handed reliever Peter Strzelecki for cash. The 30-year-old has a 5-6 record with a 3.44 ERA in 77 appearances. The Pirates also made waiver claims on first baseman/outfielder Trey Cabbage and infielder Tristin Gray, adding them to the 40-man roster for now. Finally, they non-tendered first baseman/outfielder Connor Joe, outfielder Bryan De La Cruz, and right-hander Hunter Stratton, but are working on a new deal for Stratton.

What's Left To Do

The Pirates' biggest need this offseason is offense. Their lineup was towards the bottom in most major offensive categories last season, and they need to add some power. They will be looking for help in the outfield and at first base and may also seek an everyday shortstop. While offense is the primary focus, bullpen upgrades are also necessary.So far, it's been a relatively quiet winter on the North Shore of Pittsburgh, but the same can be said for the rest of the league. Most notable free agents are still available, and the trade market has yet to fully develop. There has been hardly any activity since the Pirates acquired Strzelecki on Nov. 22. Earlier in the winter, John Perrotto, Griffin Floyd, and I all named three free agents the Pirates should target. Many of those names are still on the market.

Former Pirates Great Dave Parker

Former Pirates' great Dave Parker is once again up for the Hall of Fame via the Golden Era committee. He needs 12 of 16 votes to be elected into Cooperstown on Sunday. This is an important event for Pirates fans and for the history of the team.

Rule 5 Draft

The Rule 5 Draft will take place on Wednesday. The Pirates are unlikely to make a pick this year, as they did last year. However, they can add prospects through the minor-league phase of the draft after the MLB phase concludes. An example of this is Joshua Palacios, who was selected in the minor-league portion two years ago.

Blockbuster Trades and Free Agent Deals

Expect to see some blockbuster trades and free agent deals around the league. All signs point to superstar outfielder Juan Soto getting closer to a decision. After that, the rest of the free-agent market should start to heat up. The most notable name who could be on a new team after the meetings is Chicago White Sox left-hander Garrett Crochet. It's going to be an exciting week with a lot of potential for the Pirates and the rest of the league.