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

The Pirates should have these three things at the top of their to-do list this week.

Jun 5, 2024; Pittsburgh, Pennsylvania, USA;  Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout before the Pirates host the Los Angeles Dodgers at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
Jun 5, 2024; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates general manager Ben Cherington speaks on the phone in the dugout before the Pirates host the Los Angeles Dodgers at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images
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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.

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