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The Winter Meetings are upon us. Baseball’s leading minds will convene at the Gaylord Opryland Resort & Convention Center in Nashville, Tenn., beginning today. Over the next few days, they will lay some of the groundwork for the rest of the offseason, and we will begin to hear from them regarding where they see their clubs and which needs are their top priorities. 

Pirates general manager Ben Cherington has a lot of things to consider regarding the upcoming team, and he’ll begin making some decisions on the 2024 club in Nashville. At the very least, we will see how the Bucs use -- or don’t use -- the Rule 5 Draft. Here’s a guide to the 2023 Winter Meetings from Pittsburgh’s position.

Key events
• Sunday, Dec. 3: Hall of Fame Contemporary Era ballot results released (Cito Gaston, Davey Johnson, Jim Leyland, Ed Montague, Hank Peters, Lou Piniella, Joe West and Bill White)
• Tuesday, Dec. 5: Draft Lottery
• Wednesday, Dec. 6: Rule 5 Draft

Club needs
The clearest need is starting pitching. The Pirates’ starting staff is largely inexperienced beyond Mitch Keller and Johan Oviedo, who will reportedly undergo Tommy John surgery this offseason. JT Brubaker will return from his Tommy John surgery early next season, but it’s unclear exactly when. So the Bucs need to secure a veteran starter.

To supplement the offense, it would be ideal if the Pirates added a first baseman with some pop. Rhys Hoskins, one of the youngest players in the free agent pool at first base, is the darling of this year’s class at age 31 after slugging 30 homers in 2022 before missing the 2023 season with a left ACL tear. But Carlos Santana, who launched 23 homers in 2023, put up a solid 2.7 bWAR last year, and he has expressed a desire to return to Pittsburgh.

Potential trade candidates
Let’s put the obvious up front: Teams will constantly be inquiring about Pirates closer David Bednar. He’s one of the best in the game at what he does, and he converted a National League-leading 39 saves in 2023. However, with him not becoming a free agent until the ‘27 season, his asking price will be astronomical. 

The Pirates could use their young middle-infield depth to swing a trade. The second-base position is crowded with guys taking their first steps in the Majors. Does another team see that as an area to add a potential long-term piece, and does that team have someone in one of Pittsburgh’s areas of need to swing a deal?

Prospects to know
If you don’t know Paul Skenes by now, take five minutes to watch his highlights and then return to this newsletter. That unbelievable arsenal you just saw has a chance of reaching the Majors in 2024. It seems fast given he was the No. 1 pick in the ‘23 Draft, right? However, Skenes, the No. 3 overall prospect in MLB, has been said by many prospect experts to have the Major League-readiness of Stephen Strasburg as a prospect, who was another former No. 1 overall pick in the Draft that reached MLB within a year. 

Meanwhile, Jared Jones, the Pirates’ No. 3 prospect, has 82 innings at Triple-A Indianapolis, a level he reached at age 21. And while those innings weren’t as strong as his great numbers to begin 2023 in Double-A, with the Bucs needing starting pitching help, maybe they bring him up sooner than later, though his high strikeout numbers also warrant consideration as a possible back-end reliever in the future.

Rule 5 Draft
The biggest candidate to be plucked from the Pirates by another team in this year’s Rule 5 Draft is Matt Gorski. The 25-year-old outfielder has hit 20 or more home runs with 20 or more steals in each of the past two Minor League seasons, but he’s had some trouble staying healthy, including a hamstring issue last season and a quad injury that sent him to the 60-day IL in 2022.

On the acquisition side, the Pirates have looked for pitching help in recent Rule 5 Drafts. In its two selections with Cherington as GM, Pittsburgh took right-hander José Soriano in 2020, who wasn’t able to return from Tommy John surgery quickly enough to reach the retention threshold, and left-hander Jose Hernandez in ‘22, who had a 4.97 ERA in 50 games last season and remains with the club.

Burning question
Will the Pirates make moves as if they are turning the corner or as if they’re preparing to turn the corner? It’s a minor distinction, but it makes a major impact on how the 2024 team will be viewed. Cherington took over as GM in the 2019 offseason, so he and Pittsburgh’s front office are entering their fifth year under the current regime. Generally speaking, if things go right, a rebuilding effort takes about four to five years to approach a contention window, as it takes a while to develop key prospects acquired from early deals and grow a winning culture.

The Pirates came out the gate with a 20-8 record to begin the 2023 season, showing that brighter days might have finally arrived, but Oneil Cruz’s injury proved to be a crucial blow on top of injuries and regression that affected a good swath of the team’s starting pitching. Cruz should be healthy to begin next season, and Brubaker shouldn’t be very far behind. The Bucs have already inked key players Ke’Bryan Hayes and Bryan Reynolds to multiyear extensions. Will they see 2024 as an opportunity to seize and make an impact multiyear free agent deal or pull off a trade that boosts the Major League roster immediately? It’s a tough question, but one that the front office will consider and determine what makes sense for Pittsburgh’s future.