Pittsburgh Pirates: Previewing The Upcoming Winter Meetings

The MLB Winter Meetings will kick off virtually on Sunday. What moves could we expect to see from the Pittsburgh Pirates?

Ben Cherington’s first calendar year as general manager of the Pittsburgh Pirates has been pretty solid. He has overhauled the development and scouting team. This included moving Larry Broadway out of the role of farm director and hiring Scott Baker in his place.

His first draft as the general manager of the Pittsburgh Pirates was a successful one. Four of their selections are considered top 30 prospects by FanGraphs. He also helped acquire two of the team’s top 10 prospects when he traded away Starling Marte last year for Liover Peguero and Brennan Malone.

On the field, Cherington’s Pirates essentially did the job they were supposed to do. They finished 19-41, but got the number overall pick for 2021’s MLB Draft. Cherington has really done good work in turning a team that consistently sat in a mediocre state from 2016 to 2019 into a club that looks like it could be real contenders by 2023 or even 2022 if the expanded playoffs are here to stay.

Still, Cherington has work cut out for him. The farm system is in a good position, but still needs work and he has a chance of doing that this upcoming Winter Meetings. 2020’s meetings are going to be very different compared to any other winter meetings, just like everything else in 2020.

Cherington has the opportunity to really boost the rebuild. His most valuable trade chip is Joe Musgrove who’s really become an underrated pitcher in baseball. His surface numbers might not be outstanding, but he has the opportunity to be a number two starter. Since his arrival with the Pittsburgh Pirates in 2018, Musgrove has averaged 3 fWAR per 150 innings pitched.

Last season, Musgrove saw a huge rise in strikeouts, albeit at the cost of his walk rate. With two years of affordable control left and outstanding numbers under the surface, he could easily reel in a very good prospect haul.

Another arm they may shop aggressively is Steven Brault. Brault is in the opposite boat as Musgrove. He had decent numbers on the surface, but horrible ERA estimators. He still has some value as a back-end starter and Cherington should to strike while the iron is hot.

Free agent starting pitchers have been signing for above market value this offseason and with the overall depth of the market thinning out rather quickly, the Pittsburgh Pirates should capitalize on players with high value and with the market in their favor. Plus, there are many teams still on the look out for starting pitching, willing to pay a premium. Along with Musgrove and Brault, they’ll definitely listen in on any players with three or less years of control left. Josh Bell, Adam Frazier, Richard Rodriguez and Colin Moran are names that might get some attention next week.

The last day of the Winter Meetings includes the Rule 5 Draft. Currently, the Pittsburgh Pirates have one open slot on their 40-man roster. They also have the first overall selection in the Rule 5 draft. While this draft is more or less trying to find a diamond in the rough, there’s no risk associated in selecting a player.

The only thing the Pirates will have to surrender when they select a player is $100,000 to the team that they select the player from. They could pick a high-ceiling player who’s struggled so far like pitcher Riley Pint, or go with a safer pick like middle infielder Wenceel Perez.

By the end of the 2020-2021 Winter Meetings, the Pirates’ MLB roster could look a lot different. This is still a rebuilding period for the team. However, this could be a very beneficial time for the franchise and its future while it continues to get prospects ready for that 2022-2023 window.