The Pirates Are Sailing Without a Map

It’s been one week since the Pirates fired manager Derek Shelton and replaced him with former major league utilityman and Pittsburgh native Don Kelly, who served as Shelton’s bench coach for the entirety of his managerial stint. Firing the manager is one of the first moves made by an underperforming or flat-out awful ballclub, so there’s nothing surprising about Shelton getting the axe after a 12-26 start. But a manager’s record is only as good as the players on his roster and the money spent to build that roster, and Pittsburgh was deficient in both for Shelton’s entire tenure, which spanned five-plus seasons. During that time, the team posted a 308-441 record.

Now with Kelly at the helm, the Pirates are still on a ship that’s at best treading water; they are 3-3 in their six games since he took over, with five of them being decided by just one run. Perhaps Pittsburgh will be better with Kelly managing than it was under Shelton. After all, this is a team that at least has Paul Skenes and Oneil Cruz. However, there is only so much that Kelly can do here. The core problems in Pittsburgh can only be solved with a drastic shift in organizational philosophy, and that starts with owner Bob Nutting and the person tasked with executing that strategy, general manager Ben Cherington.

The ineptitude of the Pirates starts at the top with Nutting. He is the man responsible for their frugality, as they’ve run among the lowest payrolls in baseball every season, without exception, since he purchased the team in 2007: They’ve never ranked higher than 23rd in end-of-year payroll. Even if Nutting decides to invest more into the roster in the future, the Pirates are never going to be able to splurge like the Dodgers and Mets, or even the next tier of teams like the Phillies and Cubs. But as a small-market team, the Pirates receive more from the revenue-sharing pool than they put in. (Each team puts 48% of its local revenue into the pot, which is then distributed evenly among the 30 teams.)

Trying to glean what they’ve done with that money is… murky at best. USA Today’s Bob Nightengale had a timely report on Sunday, noting at the end of his weekly notes that the Pirates are “one of the most profitable teams in all of baseball” and that they keep a “huge chunk” of the money received via revenue sharing instead of putting it back into the club, which is the whole purpose of redistributing the pool money to smaller-market teams. The Pirates profit from the mere structure of revenue sharing itself, and hoarding that cash is antithetical to the cash heading their way in the first place.

But even though Nutting has hung onto more revenue-sharing money than he should, it’s still Cherington’s job to do more with less, and for the most part, that hasn’t been the case.

To Cherington’s credit, the Pirates have been pretty good at developing pitching since his arrival after the 2019 season. They currently rank 13th in the majors in pitcher WAR, with a 13-man staff almost entirely drafted or acquired by Cherington. Skenes, of course, leads the rotation; he’s already emerging as one of the best no. 1 draft picks of the century, meteorically rising to his perch as the face of the franchise and one of the most recognizable players in the whole league. The lone arm on the staff who came to the organization prior to Cherington’s hiring, Mitch Keller, was drafted by the Pirates in 2014, while Neal Huntington was still running things — but the right-hander didn’t blossom until after Cherington took over. More pitching help should be on the way later this year, with Jared Jones due back from an elbow injury around midseason and top prospects Braxton Ashcraft, Hunter Barco, and Bubba Chandler all pitching for Triple-A Indianapolis.

The same cannot be said for the Pirates at the plate. They have the second-worst offense in baseball by wRC+ both for this season (75) and since Cherington was hired (83). Only two of the 13 hitters on the roster were drafted or signed as international free agents by Cherington’s front office. One of those two is backup catcher Henry Davis, the no. 1 pick in the 2021 draft who, at age 25, can pretty safely be described as a bust.

And despite all of the losing and therefore higher draft picks, the Pirates farm system lacks promising position players. Termarr Johnson, the no. 4 pick in 2022, has dropped off our Top 100 Prospects list. Center fielder Konnor Griffin (no. 72) is the only Pirates position player on that list currently, and although Eric Longenhagen bumped him up to a 50 FV in his post-spring training update, at age 19, Griffin has a ways to go before impacting the major league roster.

That still leaves a couple of avenues for Cherington to add length to his meager lineup: trade and free agency. But recent efforts there have failed, too. Bryan De La Cruz, acquired at the 2024 trade deadline from the Marlins, was non-tendered after the season; Isiah Kiner-Falefa, who came over in a trade from Toronto, has predictably fielded quite well without offering much with the bat. Neither Tommy Pham nor Adam Frazier, both signed to one-year deals in the offseason, have managed to be replacement level. Oh, and those one-year deals? They’re the only length of contract to which Cherington has signed any player in his six offseasons on the job.

So, Nutting has failed to provide Cherington with enough, and Cherington hasn’t done enough with what he’s been provided. What, then, can they do differently? Well, it’s a copycat league, so they should probably just start by looking around.

We know Pittsburgh is never going to be a big spender, but plenty of teams have found success without $200 million payrolls, and they don’t all do it the same way. The Guardians roster players they’ve drafted and developed at rates at or near the top of the league every single year; the Rays, of course, love wheeling and dealing for undervalued players, and they construct their major league rosters largely via trade. But what both teams do that the Pirates don’t is supplement their rosters with meaningful free agent signings. Neither Cleveland, nor Tampa Bay plays at the top of the market, but they also aren’t afraid to commit to players they like for multiple years or a little more money if that’s what it takes to make a deal.

Before we get to the next example, I should advise any Pirates fans reading this not to get your hopes up — that is, if you have any left — because this is never going to happen as long as Nutting owns the team. But for a moment let’s consider the team that, in an perfect world, would be the ideal organization to emulate: the San Diego Padres. They are the best evidence for the difference that one owner can make, because under the late Peter Seidler, they drafted and developed well, traded prospects to acquire established major league talent, and invested their revenue-sharing money back into their roster through free agency, even paying top dollar for top free agents when necessary. San Diego is the 30th-largest media market in North America, according to Nielsen; Pittsburgh ranks 27th. Realistically, the Padres have overextended themselves — which is why they traded away Juan Soto in December 2023 and reportedly considered dealing Dylan Cease before this season — but there is a massive gap between San Diego’s estimated $262.2 million luxury tax payroll for 2025 and the $112.9 million that Pittsburgh is projected to spend. And the most important thing is this: The Padres are winning. Since the start of the 2020 season, which was Cherington’s first year running things in Pittsburgh, San Diego has the seventh-best record in the majors (407-343, .543) and played in three of the past five postseasons.

Improvements can and should also be made at the bottom rungs of the organization, and considering Cherington’s terrible track record with hitters, the focus should be on offensive player development. I’m not privy to how the Pirates approach this now, but it’s clear that whatever they’re doing isn’t working. There needs to be some level of accountability, whether it’s in the form of changing the messaging to the hitters, the people delivering the messaging, or both. Something of an internal audit would be a great first step toward figuring out what exactly has gone wrong and what the organization should do to fix it.

None of the changes the Pirates need to make can happen right away. Unless Nutting drastically increases payroll — which is extremely unlikely — it’ll probably take at least a few years to overhaul the operation. Fans won’t flock back to PNC Park just because there’s a better plan in place; there needs to be something different on the field, too. And by different, I don’t just mean peering into the dugout and seeing Kelly instead of Shelton.