Projecting the long-term outlook for the Pirates after the Mitch Keller extension

No. 1 - Established stars

Keller’s signing marks the third straight season during which the Pirates have locked up a young face of the franchise. In 2022, Pittsburgh inked Ke’Bryan Hayes to an eight-year extension, anchoring the slick fielder at the hot corner through the 2030 season. In 2023, Bryan Reynolds signed a long-term deal through 2030 and a club option for 2031.

Not only will these two stars provide valuable defensive and offensive production, the pair has stepped into a leadership role on a team full of young, developing players. Hayes and Reynolds have the potential to shape the late 2020s Pittsburgh teams, and Hayes, in particular, has been lauded for his calm, cool demeanor and his capacity for grinding his way through a season.

“I'm not the loudest person in the room, but I've always been a hard worker, at least in my eyes. I try to play the right way and go about my work day the right way with purpose.”

Bailey Falter and Colin Holderman, although not stars, are key bullpen pieces that would still be around in 2028. Holderman has the potential to develop into a high-leverage arm as he gains more experience as the presumptive setup man for the Pirates in 2024 and beyond.

No. 2 - Promising Pirates

Of course, we’ll start with Paul Skenes, who has the makings of a generational talent and is the current best pitching prospect in baseball. If Skenes makes his debut in 2024, which he seems on track to do, he will likely be around his first year or so of arbitration eligibility in 2028. Imagine a rotation that features Skenes and Keller as 1-2. If any of the other budding Pirate arms (Bubba Chandler, Jared Jones, Anthony Solometo) reaches his ceiling, the Pirates would have a solid front three that could be supplemented with trades or free-agent signings.

On the position player front, things seem much less promising. Second baseman Termarr Johnson is the only Top 100 position prospect in the Pirates’ system, and he likely won’t make it to the Majors until at least next year, if not later. Pittsburgh, though, could extend Oneil Cruz and provide a little bit more security for the future. The investment in Henry Davis at catcher this season may also play a significant role in how the Pirates approach the next several years.

The Pirates hold the No. 9 selection in the 2024 MLB Draft, a slot that could feature several available outfielders. Pittsburgh has a spotty record with player development, particularly on the position player side, and a player with natural power-speed, such as Northeastern’s Mike Sirota, could work his way successfully through the system.

No. 3 - Comparing with the rest of the NL Central

When considering the players currently signed to NL Central teams through 2028, the Reds seem to be using the same playbook as the Pirates. Fireballer Hunter Greene signed an extension prior to the 2023 season, and many of the promising young players, including Elly De La Cruz, T.J. Friedl, and Matt McLain, are a few years out from arbitration. They, like the Pirates, have five prospects on MLB.com’s Top 100 list, so reinforcements are waiting in the wings.

The window may be closing on the Cardinals, who are projected by FanGraphs to win the division this year. They have only three prospects in the Top 100, and Willson Contreras, Jordan Walker, and Nolan Gorman are virtually the only major players who are likely to be on the team in 2028. Similarly, the Brewers have locked in top prospect Jackson Chourio through 2033, but the majority of Milwaukee roster will be entering free agency in the next couple of years.

The Cubs have the most question marks in terms of long-term development. Dansby Swanson and Shota Imanaga are the biggest names tied to the North Side for the next several seasons, but Chicago has seven prospects ranked in the Top 100. The Cubs also have the deepest pockets and could change the divisional landscape with free-agent signings between now and 2028.

The choice to lock down Keller until 2028 alongside Hayes and Reynolds provides the Pirates with some stability. With the development of a couple of other highly ranked prospects, the addition of a few solid bats, and an extension for Cruz (if he bounces back from injury this season), Pittsburgh could be in shape to compete in the latter half of the 2020s.