Pirates 2024 Winter Meetings Preview

Major League Baseball executives from around the league are all headed to Dallas for the start of the 2024 Winter Meetings.

The Winter Meetings, which is typically the busiest week of the offseason, officially begin on Monday and run through Thursday. There will be a handful of trades, free agent signings, other rumors and news from the busy week to come.

For the Pittsburgh Pirates, there is a lot to do between now and the start of spring training. The Pirates could look to strike again at the Winter Meetings, as they have done a few times under Ben Cherington’s watch.

There are several things to look out for as the hot stove begins to boil.

What’s Been Done

Well… not much.

The most notable news from the Pirates so far this winter is several staff additions. The Pirates landed on Matt Hague to replace Andy Haines as the club’s hitting coach. Hague, who played for the Pirates for two seasons, was the Toronto Blue Jays’ assistant hitting coach in 2024.

Additionally, the Pirates added long-time pitching coach Brent Strom as an assistant pitching coach under Oscar Marin for the 2025 season. Strom, who is 76 years old, has worked with a handful of notable pitchers in his career including Gerrit Cole, Justin Verlander and many more. The newest Pirates’ staff member has helped guide his team to the World Series four times and won it all with the Houston Astros in 2017.

Looking at player additions, the Pirates swung a trade with the Cleveland Guardians last month, landing right-handed reliever Peter Strzelecki for cash. In his career, the 30-year-old is 5-6 with a 3.44 ERA across 77 appearances. Strzelecki gives the Pirates some needed bullpen depth.

The Pirates also made a pair of waiver claims in first baseman/outfielder Trey Cabbage and infielder Tristin Gray. Both players were added to the 40-man roster and provide position-player depth for the time being.

And finally, the Pirates non-tendered first baseman/outfielder Connor Joe, outfielder Bryan De La Cruz and right-hander Hunter Stratton. The Pirates are working to bring back Stratton on a new deal.

What’s Left To Do

Well… a lot.

The biggest need for the Pirates this offseason is offense. Pittsburgh needs to add some thump to its lineup, a unit that was towards the bottom in most major offensive categories a season ago.

The Pirates will be looking for help in the outfield and at first base and could look to find an everyday shortstop. And while offense is primary focus for the Pirates, bullpen upgrades will also be needed.

While it’s so far been an inactive winter on the North Shore of Pittsburgh, the same could largely be said for the rest of the league. Most notable free agents are still available and the trade market has yet to take shape. In fact, there’s hardly been any activity since the Pirates acquired Strzelecki on Nov. 22.

Earlier in the winter, myself, John Perrotto and Griffin Floyd all named three free agents the Pirates should target this offseason. Most of the names we gave still remain out there.

Anything Else?

Yes, it’s the Winter Meetings after all!

Former Pirates’ great Dave Parker is once again up for the Hall of Fame via the Golden Era committee. Parker will need 12 of 16 votes to be elected into Cooperstown on Sunday.

The Rule 5 Draft will take place on Wednesday. The Pirates probably won’t be making a pick, as was the case last year. But 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.

And of course, 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.

Stay tuned for what should be a fun week.