Top 3 goals the Pirates should set heading into the Winter Meetings

The 2024 Winter Meetings officially kick off on Monday, Dec. 9, though key executives and agents began to arrive on Sunday. Teams will look to do a lot of their offseason shopping over the course of the next week. The meetings conclude on the 12th, with the Rule 5 Draft also taking place on the 11th. It's one of the most active weeks in Major League Baseball, with potentially only the week leading into the trade deadline rivaling it.

That means, with the eyes of the world on the game, it's time for the Pittsburgh Pirates to start making some moves. The Pirates have something decent brewing, but more needs to be done to complete the picture.

The Winter Meetings provide a great opportunity for them to improve their current situation. The Bucs need to get their priorities straight as the Winter Meetings kick off, so what should be their top three goals this week?

3 goals for the Pittsburgh Pirates during 2024 MLB Winter Meetings

Trade some starting pitching

If there's one thing the Pirates have, it's a deep starting rotation. They already have their 1-through-3 set with Paul Skenes, Jared Jones, and Mitch Keller. The back end of the rotation should consist of some mix of Luis Ortiz, Bailey Falter, and Johan Oviedo, with Mike Burrows and Braxton Ashcraft also on hand. That's not even mentioning the immense amount of young talent the Pirates have coming up their organizational pipeline.

The Pirates only have five rotation spots, and three are already filled for the foreseeable future. Sure, not every prospect the Pirates have is going to hit the ground running, or even pan out, but that's only more of a reason for them to make a trade -- or multiple trades -- involving some of their young hurlers.

On top of that, the cost of starting pitchers is insane right now. Matthew Boyd, who hasn't started more than 15 games since 2019, just recently signed a two-year deal with a $14.5 million AAV. Frankie Montas, a pitcher who hasn't put up an ERA+ above 100 since 2021, also signed a lucrative two-year contract with a $17 million AAV. Luis Severino may have been the most surprising, inking a three-year contract (option after Year 2) with the Athletics for an AAV of nearly $23 million. 2024 was the first season since 2018 in which he started more than 20 games, but he only had an ERA+ of 101, making him a roughly league average pitcher.

If back-of-the-rotation starters like Boyd and Montas are getting about $15 million a season, and middle-rotation arms like Severino are receiving over $20 million a season, then the Pirates should be in a prime position to get something really good out of some of their starters. Not trading at least one would be a massively wasted opportunity.

Add some power

The Pirates' offense last year was bad, and that's putting it nicely. They ranked in the bottom five in OPS, wOBA, and wRC+, with the seventh-fewest runs scored. With the sort of starting rotation the Pirates have, not giving themselves a fighting chance with the lineup represented another big wasted opportunity last season. So far, the Pirates haven't directly improved their lineup this offseason. Sure, firing Andy Haines and bringing in Matt Hague should be a big help, but obviously, more needs to be done.

The easiest way to improve a lineup's run productivity is to add power. That's another area the Pirates struggled in. Their .137 isolated slugging percentage was the fifth lowest in baseball, while their slugging percentage was the fourth worst. The team, as a whole, had just 160 home runs, which was the sixth fewest among all 30 teams.

The Pirates need at least one corner outfielder and a first baseman. Those are two positions where you can find power bats with ease. The free agent market has some decent options. Carlos Santana, Joc Pederson, Max Kepler, Michael Conforto, and Randal Grichuk represent some realistic options. If the Pirates want to get totally serious and bold, Christian Walker or Anthony Santander should be their top options.

The trade market should also house plenty of options for a slugger. The first base trade market should be plenty active, with the likes of Alec Bohm, Ryan Mountcastle, Josh Naylor, and Yandy Diaz as players who could be moved either during the Winter Meetings or later on during the offseason. 

Trading some of the young pitchers for power bats should be a top priority during this Winter Meetings. The Pirates have the pieces to make impactful trades. Now is the time to do so, because the foundation is in place. It's time to build upon that foundation and put some power into the lineup.

Improve the bullpen

At this time last year, the Pirates' bullpen looked like it could be one of the best in baseball. With breakouts from Ryan Borucki, Dauri Moreta, and Colin Holderman, along with All-Star David Bednar and rookie Carmen Mlodzinski all returning for 2024, a Pirates lead after the sixth inning looked like it would be a sure thing 99% of the time. Then, they made a huge splash by adding Aroldis Chapman at the end of January.

Somehow, the Pirates' bullpen quickly started to fall apart despite their foundation. Moreta underwent Tommy John surgery at the end of spring training, while Borucki landed on the IL during the season's first week. The southpaw wouldn't return until September. Bednar was not his normal self, and Holderman completely fell apart after the All-Star break. Chapman was good, but he certainly had his patented moments of strife, too.

The Pirates still have a solid foundation to work with. Bednar's season might end up being a fluke, given his stuff looked better than ever. Kyle Nicolas had a fine rookie campaign, while Dennis Santana was a huge surprise and may have even put himself in contention for a high-leverage role for next season. Mlodzinski will also likely play a significant role. But there's still work that needs to be done.

The Pirates only have one lefty reliever on the 40-man roster, and that's Joey Wentz. Wentz didn't do badly in his short late-season showing with the Bucs, but he is far from a good bet. Aside from that, the team could definitely use another reliever with closing experience in the event Bednar doesn't rebound.

There should be plenty of opportunities to add relievers during the Winter Meetings. Free agent options like A.J. Minter, Jose Leclerc, Tim Hill, Hoby Milner, Carlos Estevez, Andrew Kittredge, David Robertson, Kenley Jansen, Blake Treinen, Kirby Yates, and Andrew Chafin, along with a handful of others, are still looking for contracts. Plus, there are always teams willing to move relievers in trades.