The calendar may only be about to flip to December, but the Pirates have already had a fairly active offseason.

They addressed their most significant need by acquiring a pair of first basemen in Ji-Man Choi (trade), Carlos Santana (signing) in a span of three weeks. They cleared the way for the youth movement up the middle by trading Kevin Newman, their longest-tenured player, to the Reds. There’s also the litany of shakeups to the 40-man roster due to various deadlines.

Pittsburgh, on paper, appears to be a better team now than one month prior. Yet there is still work to be done for the Pirates’ brass. The emphasis remains on the future, but Pittsburgh can beef up its roster in the present. There are several areas the Pirates would like to address, and the Winter Meetings are just the place to do so.

Key Events

• Sunday, Dec. 4: HOF Contemporary Era ballot results released (Albert Belle, Barry Bonds, Roger Clemens, Don Mattingly, Fred McGriff, Dale Murphy, Rafael Palmeiro, Curt Schilling)
• Monday, Dec. 5: All-MLB Team announced
• Tuesday, Dec. 6: Inaugural Draft Lottery, AL/NL Relievers of Year announced
• Wednesday, Dec. 7: Rule 5 Draft

Club needs

With first base shored up, the Pirates can shift their attention to several other position groups. One of those is the starting rotation.

Mitch Keller, Roansy Contreras and JT Brubaker appear to be locks. Johan Oviedo stands to be part of the rotation as well, especially considering the Pirates stretched him out to be a starter after acquiring him in the José Quintana deal. The final spot is a bit of a mystery. Bryse Wilson added a splitter towards the end of last season, but will that be enough to consistently provide length? Luis Ortiz dazzled in his cup of coffee, but will he refine and deepen his repertoire?

Catcher could be another one as well. The club has two backstops on the 40-man roster: Ali Sánchez and Endy Rodriguez. Sánchez has seven Major League games on his resumé. Rodriguez, the Pirates’ No. 6 prospect per MLB Pipeline, has yet to debut. In an ideal world, they will sign a veteran catcher who can serve as a bridge to Rodriguez and Henry Davis, the Pirates’ No. 1 prospect per MLB Pipeline.

Potential trade candidates

Bryan Reynolds has perpetually been the subject of trade rumors, and that chatter will only intensify in the coming weeks now that he has requested a trade, a source told MLB.com's Mark Feinsand. Reynolds, 27, is an All-Star with a career .842 OPS and 126 wRC+. Needless to say, there might be several teams willing to cash in their prospects for Reynolds’ prime years, as he isn't a free agent until after the 2025 season.

Prospect to know

The Pirates added four Rule 5-eligible prospects to their 40-man roster several weeks back: Rodriguez, right-handed pitcher Mike Burrows (PIT No. 8), infielder/outfielder Jared Triolo (PIT No. 24) and right-handed pitcher Colin Selby. General manager Ben Cherington noted that there is a viable path to all four contributing at the Major League level at some point in 2023.

Rodriguez, 22, and Burrows, 23, will likely begin the season with Triple-A Indianapolis but could both be with the big league club by the summer. Triolo, 24, is still growing offensively but provides stellar defense and great baserunning (24 steals). Selby, 25, transitioned to a full-time reliever in 2021 and posted a 2.27 ERA with 43 strikeouts in 35 2/3 innings in 2022 with Altoona and Indianapolis, then allowed just two runs in nine innings in the Arizona Fall League.

Along with Rodriguez, Burrows, Triolo and Selby, the farm system features a plethora of prospects who could conceivably debut next season. The list includes Davis, Quinn Priester, Nick Gonzales, Malcom Nunez, Matt Gorski, Blake Sabol and Tahnaj Thomas.

Rule 5 Draft

Regardless of how many prospects the Pirates protected, some combination of players was going to be left out. Rodriguez, Burrows, Triolo and Selby were added. Nunez, Gorski, Thomas and Sabol headlined the group that was not. On the flip side, the Pirates could use the Rule 5 Draft to acquire pitching depth. Cherington has discussed the desire to add more swing-and-miss to the bullpen, and the Rule 5 Draft could be a means to do so.

Burning question: Will the Pirates trade Reynolds?

The question circulated after he became an All-Star. The question circulated during Spring Training. The question circulated at the Trade Deadline. The question circulated at the GM Meetings. It’s the question that will not evaporate. Yes, this is the question that will follow the Pirates around at the Winter Meetings.