This story was excerpted from Justice delos Santos’ Pirates Beat newsletter. Jake Crouse wrote this week's edition. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

The Pirates took strides in 2023, making the upcoming offseason even more important as the club tries to construct its first winning record since ‘18 and its first postseason appearance since ‘15. Here’s a primer to Pittsburgh’s offseason plans.

Which players are free agents?

Designated hitter Andrew McCutchen, infielder/outfielder Chris Owings, left-hander Caleb Smith and right-hander Vince Velasquez.

The most notable is McCutchen, a fan favorite who has resided in Pittsburgh for many years even while playing on other teams. McCutchen sustained a partial tear of his left Achilles in early September just one homer shy of the 300 mark for his career. Pirates GM Ben Cherington said of McCutchen before the season ended that “there’s a desire for him to return."

Velasquez made only eight starts last season before undergoing surgery on his right UCL in June. His return to play was projected at 11-12 months at the time, so he would not be available on Opening Day if a reunion was in the cards.

Are any of them likely to receive qualifying offers, and what is the deadline for that?

No. The decision must be made by the fifth day after the World Series ends.

Which players have options?

Jarlín García has a $3.25 million club option. García never threw a pitch for the team in 2023 due to a nerve issue in his left arm, but he has limited left-handed batters to a .605 OPS during his career. The Pirates could decline it and use the money this offseason on other areas of improvement or renegotiate a new deal hoping García is healthy. They must decide this by the fifth day after the World Series ends.

Who might be a non-tender candidate, and when does the club need to make that decision?

The most likely player to be non-tendered is Miguel Andujar. The outfielder played only 30 games for the Bucs in 2023. The outfield group is crowded; Bryan Reynolds, Jack Suwinski and Connor Joe should be the regulars, while Joshua Palacios made strides offensively and Henry Davis will likely continue to see time in right field. The non-tender deadline is 8 p.m. ET on Nov. 17.

Who needs to be added to the 40-man roster this winter to avoid the Rule 5 Draft?

Last year, the Pirates emptied spots for Endy Rodríguez, Mike Burrows and Jared Triolo. This year, there isn’t a player who would likely be seen in the same light as the highly touted Rodríguez or Burrows. 

Braxton Ashcraft, Pittsburgh’s No. 12 prospect per MLB Pipeline, is the biggest name of this year’s group. He posted a 2.39 ERA in 19 starts this past season. However, he only pitched 52 2/3 innings following a recovery from Tommy John surgery. No. 18 prospect Tsung-Che Cheng is also interesting; his primary position of shortstop is fairly saturated at the moment, but the reports on him have been good. The Pirates shouldn’t have much trouble fitting either on the roster after free-agent departures and with a few players being non-tender or DFA candidates.

The other Rule 5-eligible Top 30 prospects who are at Double-A or Triple-A: Matt Gorski (No. 20), Malcolm Nuñez (No. 23) and Jase Bowen (No. 27). The 40-man roster must be set for Rule 5 protections by Nov. 14 at 6 p.m. ET, and the Rule 5 Draft is on Dec. 6.

What kind of help do they need and will they be active in free agency? Who might they target?

The Pirates ended the season with effectively two full-time starting pitchers: Mitch Keller and Johan Oviedo. Two interesting free-agent targets to bolster the group are right-hander Jack Flaherty and Kyle Gibson. Since his breakout 2019 season, Flaherty has posted a 4.42 ERA in 64 appearances (59 starts) and may be an ideal bounceback candidate. Gibson had a 4.88 ERA over the past two seasons with the Phillies and Orioles, but with 11 years of MLB experience, he could provide veteran leadership in a still largely inexperienced rotation.

Who might they be willing to trade?

If the Pirates are going to trade for any notable players -- a José Quintana reunion, anyone? -- they could trade from an area of prospect/young MLB player depth like a middle infielder, but it might not be enough. Cherington has shown he is not eager to deal Top 30 prospects, but after his best regular-season record overseen as GM (76-86), could that formula begin to change if he sees a contending window arriving?