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 2024-25 offseason is right around the corner, and plenty of eyes are going to be on the Pirates as they enter a pivotal season. Let’s take a look at some of the most important dates and roster questions as we approach the winter.

WHO IS A FREE AGENT?

The Pirates currently have five players on their 40-man roster who will be free agents, and one veteran with a club option that will surely be declined. Andrew McCutchen, Aroldis Chapman, Jalen Beeks, Ryan Borucki and Yasmani Grandal are on expiring deals, and while Marco Gonzales’ contract has a $15 million club option, it’s unlikely to be picked up since he is expected to miss most of the 2025 season.

Of course McCutchen is the biggest name here, establishing himself as one of the greatest Pirates in franchise history. There doesn’t seem to be much drama on if a return is going to happen, either. McCutchen reaffirmed at the end of the season he wanted to return, and general manager Ben Cherington said earlier this month that, “we'd love to find a way for Andrew to finish his career in a Pirates uniform.” He should come back.

No free agent is expected to be extended a qualifying offer, but the deadline to do so is the fifth day after the World Series. The Pirates will have to make their decision on Gonzales’ club option by then, too.

WILL THERE BE A ROSTER CRUNCH?

The Pirates have six players currently on the 60-day injured list who will need to be added back to the roster within five days of the end of the World Series (Ben Heller, Daulton Jefferies, Dauri Moreta, Johan Oviedo, Hunter Stratton and Endy Rodríguez). At least one roster spot will need to be cleared in order to do so, so there will be some non-tender and waiver-wire moves by then.

Heller and Isaac Mattson are two veteran relievers who were added late in the season and appear likely to be dropped, but the Pirates will need to make decisions on more established players at some point this offseason. Jefferies, Connor Joe, Liover Peguero, Alika Williams, Ji Hwan Bae, Joshua Palacios and the injured Stratton all seem like potential candidates to be non-tendered or traded to clear roster space.

Unlike recent years, though, the Pirates don’t seem to have many Rule 5 decisions to make this year after they added Billy Cook and Nick Yorke to the roster in the final month of the season. Omar Alfonzo is the only player inside their Top 30 Prospects who is Rule 5 eligible (No. 26), but they could probably sneak the High-A catcher through for another year. Outfielders Sammy Siani and Matt Gorski are both in the upper levels of the Minors and are coming off good campaigns, but might not fit into the Pirates' outfield plans.

Teams must add Rule 5-eligible prospects to the roster by 6 p.m. ET on Nov. 19, while the tender deadline is 8 p.m. ET on Nov. 22.

WHAT WILL HAPPEN WITH FREE AGENCY AND TRADES?

Teams are eligible to start signing players from other clubs five days after the World Series, and to start making the trades the day after the World Series concludes. Cherington said in his year-end media availability that he believes team payroll will increase for 2025, so the Pirates should be active on both fronts.

I listed some free agents who would be good potential fits for the Pirates in a previous newsletter, but the bullpen, first base and outfield look like the team’s most prominent needs.

The Pirates finished 27th in bullpen ERA (4.49) and are in need of depth, left-handed options and at least one more leverage arm to pair with David Bednar, who was removed from the closer role for the final month of the season. First base and outfield could be impacted if the Pirates decide to move Bryan Reynolds to the infield, but nothing was imminent when Cherington last spoke. The outfield market looks to be deeper than the first-base free-agent options, but trades are always a possibility.

The Pirates have plenty of pitching to offer in trades, both with Minor League prospects and Major League arms. Cherington has discussed wanting to convert some of that pitching depth to hitters, and this offseason seems like a good opportunity to do so.