Three ways Pirates can fill needs at Winter Meetings

December 4th, 2024

This story was excerpted from Alex Stumpf's Pirates Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

The MLB Winter Meetings are less than a week away, and while the Pirates have traditionally not made their big move of the winter at the Meetings, they usually address an area of need or two that week. They were looking for veteran starting pitching last year and swung a trade for Marco Gonzales. In 2022, they needed arms and picked up Vince Velasquez and Jarlin Garcia.

This winter, though, the focus is more on bats. They could use some bullpen help, but they have a hole in right field after non-tendering Bryan De La Cruz and Connor Joe. They also need clarity at first base, whether that’s bringing in a player or shuffling someone to first base, the latter of which would likely result in a need at another position. They need bats, and next week at Dallas is a great opportunity to get some.

What’s the best way to do that? There are plenty of ways to add players, like the Rule 5 Draft or waivers, but for a team looking to compete in 2025, they need to add impact players. The three best ways to do that are clear.

TRADE PITCHING PROSPECTS

When you think of ways to improve a roster, this is the quintessential move. Improve your current team by dealing Minor Leaguers who could help the other team down the road while they’re rebuilding. The Pirates boast the best collection of Minor League pitching in the game, according to MLB Pipeline, headlined by three Top 100 Prospects: Bubba Chandler (No. 15), Braxton Ashcraft (No. 85 ) and Thomas Harrington (No. 91). That trio probably isn’t up for discussion, but there is still plenty of depth available that would be coveted by other clubs.

General manager Ben Cherington discussed at the Trade Deadline how Pittsburgh could deal some pitching prospects for hitters. We saw it with a couple of prospect-for-prospect deals (Nick Yorke and Billy Cook). Whether it’s acquiring a young player who may be blocked with their current team or a veteran, this might be the Pirates’ best path to acquiring some offensive help.

TRADE MAJOR LEAGUE PITCHING

The starting-pitcher market has been pretty expensive the first month of the offseason, especially for middle-of-the-rotation arms. That could be to the Pirates' benefit for any team that is looking to bolster their rotation for 2025, but may not be able to shell out the cash for a free agent.

Paul Skenes, Mitch Keller and Jared Jones won’t be touched, obviously, and Johan Oviedo’s value is probably too low right now as he comes back from Tommy John surgery. Bailey Falter and Luis Ortiz showed that they are quality starters, but could be attractive trade pieces if the Pirates want to dangle them. Ortiz is still pre-arbitration, and Falter is a Super Two player with four years of control remaining. They could be the centerpiece of a trade for a bat, and could either be replaced by a reclamation project or one of their pitching prospects.

Cherington expressed earlier this offseason that he is open to trading Major League players if it makes the 2025 team better. If they were to do that, trading from an area of strength and depth makes the most sense.

HIT THE FREE-AGENT MARKET

OK, so they won’t sign Juan Soto. There are still plenty of outfielders on the market who would make sense. Players like Max Kepler, Michael Conforto, Tommy Pham, Jesse Winker and Mark Canha could be good value for the outfield. At first base, Carlos Santana expressed interest in the past about returning to the Pirates. And, of course, there are dozens of relievers who could all be theoretical fits, as they’re going to need a lefty and a leverage reliever or two, especially since Aroldis Chapman is now with the Red Sox.

The Pirates have shown they’re willing to use the whole offseason to sign free agents -- they inked Yasmani Grandal just before Spring Training and Michael A. Taylor in March of last year -- because there is no timetable for when they have to make a deal.

Well, if there is no schedule for when deals have to get done, why not the Winter Meetings?