What the Pirates need to do now to extend their impending playoff window

The playoff window, a period in which a team (often composed of a fairly stable core of players) consistently competes for a playoff spot, is a time of enthusiasm, hope, and a few gambles. With rookie sensations Paul Skenes and Jared Jones making their debuts in 2024, the Pirates seem to be on the verge of one such window, but how can general manager Ben Cherington and his staff maximize Pittsburgh’s chances of a deep playoff run?

Consider the Duration

Both the Society for American Baseball Research and Fangraphs conclude that the average playoff window lasts five years. Despite a recent bump in the Pirates’ chances to make the playoffs from 10.5 to 15.6 percent since June 1, the team’s playoff window won’t begin in earnest until 2025. Skenes and Jones may be sailing in the big leagues, but their fellow prospects Bubba Chandler and Anthony Solometo have hit a road bump in Double-A and need more seasoning.

The window will likely be closing by 2028. Yes, Mitch Keller, Bryan Reynolds, and Ke’Bryan Hayes will still be under contract, and most of the Pirates’ prospects will have a few seasons under their belt, but most small-market teams fail to compete for longer periods of time.

With this in mind, the time for moves is now. The Pirates functionally have just three or four Trade Deadlines and offseasons to piece together the best team to support their budding stars.

Shell Out (Reasonably)

Cherington has locked in key pieces such as Keller and Reynolds to long-term deals, and those extensions have already begun to pay dividends. Still, the franchise could afford to take a few gambles early in the window to bolster both the roster and the fanbase’s hopes. Even one significant trade for a controllable talent at the Trade Deadline in 2024 would give the team momentum heading into the real make-or-break years.

The White Sox are allegedly open to offers for center fielder Luis Robert Jr., and the Pirates certainly have a glut of right-handed pitching talent in the upper minor leagues. Chicago’s pitching prospects have a longer road to the Majors than Pittsburgh’s budding arms. Robert, who is under team control until 2027, would likely command two or three of the Pirates’ top prospects, a price that is likely too high for Cherington or fans to stomach. Especially when one considers his injury-prone nature and high strikeout rate.

Also rumored to be on the trade market is Jazz Chisholm Jr., who has two more years of arbitration. While he may more likely go to an immediate contender, Chisholm’s flexibility in the field would be a boon for the Pirates. Despite Nick Gonzales’s recent success, the real future of second base for Pittsburgh is Termarr Johnson, who is less than a week shy of his 20th birthday and has yet to see Double-A ball. Chisholm could man second and then move to the outfield when Johnson appears ready to make an impact in the Majors. That is, unless Johnson is roped into a high-profile trade like those outlined above, which is doubtful.

Commit to Free Agency

Consider the past few World Series winners. Those teams were full of homegrown stars, but they don’t make it to the championship without a key free-agent or two. Corey Seager, an obvious example, won the World Series MVP in the second year of his titanic contract. Of course, the Pirates are never going to be spending Corey Seager money, but longer windows result from a willingness to spend big. In Fangraphs’ model, the Pirates’ last window was only three years and the payroll still increased by nearly 35 percent.

With this in mind, the 2024 offseason is key. The Pirates likely need at least a first baseman and a mid-rotation starter. (I don’t see Pittsburgh picking up Marco Gonzales’s $15 million club option for next season.) Ryan O’Hearn of Baltimore is a lower-tier option in a first-base class that features Pete Alonso, Paul Goldschmidt, and (assuming he opts out) Rhys Hoskins, plus Jack Flaherty, who seemed an attractive free-agent pairing with the Pirates prior to this season, will be back on the market after 2024. Filling those spots would help Pittsburgh take a big step forward in order to target a legit outfield bat at the 2025 Trade Deadline.

Pirates fans are living in exciting times and at the very least get to see Jones and Skenes trot out back-to-back for the remainder of the season (or until the Bucs shut their young arms down). If Cherington and the front office handle the next year or so right and spend a little money, Pittsburgh could be contenders for the next several years.