It took longer than originally hoped, but does general manager Ben Cherington finally have the Pittsburgh Pirates in good shape to contend now and in the future, and in turn, may he have (gasp!) earned a contract extension? There are plenty of parallels to draw between the tenures of Cherington and his predecessor, Neal Huntington, who was hired late in the 2007 season and fired after the 2019 season. In between, Huntington was responsible for Pirates teams that earned Wild Card playoff spots for three consecutive seasons beginning in 2013.
Like Cherington, Huntington ostensibly came to Pittsburgh with a five-year plan. It might be fair to point out that, as far as this writer can tell, neither ever used the words “five-year plan” to describe his rebuilding effort. The press and the fans used those words for them, and five years does seem like a reasonable enough period to rebuild a baseball team. Or does it? It took him more than five years, but Huntington got it done. Maybe Cherington, too, has finally constructed a playoff team, albeit outside the five-year window.
“I mean, we’re just better,” Pirates left fielder Bryan Reynolds told Colin Beazley of The Pittsburgh Post-Gazette. “Everybody’s feeling that, knowing that. The goals are always the same, but they’re actually attainable now, and they haven’t been in the past, and we’ve had to pretend like they were. . . There’s been some players on other teams that we’ve been playing that [I’ll] get to first base and [they’ll] be like, ‘Man, you guys are gonna be a problem.’”
The Huntington Era
Huntington took over for the disastrous David Littlefield, who could never decide whether to make the Pirates older or younger, and seemed to change his mind with each transaction. Huntington inherited a mess, but one with a multitude of trade chips. He took on the task of rebuilding the organization by dumping salaries in return for prospects during 2008 and 2009. Unfortunately, those trade chips – Jason Bay, José Bautista, Sean Burnett, Tom Gorzelanny, John Grabow, Adam LaRoche, Damaso Marte, Nate McLouth, Nyjer Morgan, Xavier Nady, Freddy Sanchez, Ian Snell, and Jack Wilson – yielded 25 players, only six of whom appeared on their Wild Card teams of 2013-15.
However, despite getting so little in these trades, the Pirates were a postseason team in 2013. Where did the players come from? Littlefield’s drafts yielded a few useful players who became major-league ready by 2013 in Andrew McCutchen, Neil Walker, and Tony Watson. Starling Marte, an amateur free agent signed by Littlefield, emerged as a star. For his part, Huntington drafted Pedro Álvarez, Gerrit Cole, and Jordy Mercer, signed key free agents Clint Barmes, Jason Grilli, Francisco Liriano, and Russell Martin, acquired A.J. Burnett for two marginal prospects, and added Marlon Byrd and Justin Morneau in deadline deals. Manager Clint Hurdle embraced the radical infield shifts that are outlawed today. Just like that, the Pirates were a playoff team.
Unfortunately, the Pirates didn’t sustain their success beyond 2015. Cole and McCutchen were traded after the 2017 season. Huntington overpaid to obtain pitcher Chris Archer from the Tampa Bay Rays in a 2018 deadline deal. One of the pieces surrendered for Archer, pitcher Tyler Glasnow, was vocal in his belief that the Rays were far ahead of the Pirates in terms of resources available to pitchers. Citing the improvement of Cole and Glasnow on their new teams, Pirates owner Bob Nutting fired Huntington. Among the qualifications he was looking for in a new GM was someone who could “crack the code” that enables a small-market team like the Rays to succeed.
The Cherington Era and “Cracking the Code”
Enter Cherington. As is the case with all rebuilding efforts, “the code” involved tearing it down and trading higher-salaried players for prospects. Despite the Pirates’ lack of success, he had a few desirable trade chips of his own. In 2020 and 2021, he traded Josh Bell, Austin Davis, Adam Frazier, Clay Holmes, Marte, Joe Musgrove, Richard Rodríguez, Jacob Stallings, and Jameson Taillon. These deals netted 24 prospects, but like his predecessor’s “rebuilding” deals, most of those prospects didn’t contribute significantly to the big club. Only one remains in the organization, catcher Endy Rodríguez, who was assigned to Triple-A late in spring training.
Yet, although it’s taken a little longer than it took Huntington, Cherington has shaped the Pirates into a borderline contender. His drafts have made the organization rich in young pitchers. All Paul Skenes has done so far is win the National League Rookie of the Year and Cy Young Awards. The Pirates’ No. 2 prospect Bubba Chandler will begin the season in the starting rotation. Their No. 5 prospect, Hunter Barco, opens the year in the bullpen. Last year’s anemic offense should get a boost from free agents Ryan O’Hearn and Marcell Ozuna and trade acquisitions Brandon Lowe and Jake Mangum. The No. 1 overall pick from 2021, Henry Davis, has come into his own as a defensive catcher. The Pirates also have the No. 1 prospect in all baseball, Konnor Griffin, in Triple-A with an expected arrival in the majors early this season.
There are plenty of holes, too. Nick Gonzales and Jared Triolo comprise a rather uninspiring left side of the infield. After failing as a rotation piece last year, Carmen Mlodzinski is getting another shot. The additions that are expected to help the offense may weaken the team defensively. Enigmatic, multitalented Oneil Cruz remains a question mark until proven otherwise. The Pirates say he’s ready to have a big season at last. Ozuna is the latest Pirate who supposedly will “get through” to Cruz. So was Tommy Pham last season and Carlos Santana in 2023. We’ll see.
Pundits are projecting anywhere from 78 to 86 wins for the 2026 Pirates. Around 84 or 85 should put them in the postseason, or at least keep them in the race until late in the season. The sports books have the over/under at 78.5, for what it’s worth, although I believe that has more to do with how the money is flowing from the gamblers than any serious analysis. This is probably worth even less, but I have them in the 84-86 range.
In Better Shape
Getting back to Cherington’s drafts, eight players on the Opening Day roster – over a third – were drafted by Cherington. When he made Skenes the No. 1 overall pick in 2023, Cherington went against the conventional wisdom that had Skenes’s teammate at LSU, outfielder Dylan Crews, as the consensus first pick. Pirates fans on social media and talk shows went ballistic. Today, Crews is beginning this season at Triple-A for the Washington Nationals, and Pirates fans are pretending they knew about Skenes all along. Fan reaction was similar when Cherington went the high school route and selected Griffin and pitcher Seth Hernandez in the first rounds of 2024 and 2025, respectively. Now these fans are clamoring for Griffin’s major league debut, and those who saw Hernandez (Pittsburgh’s No. 3 prospect) fire 102-mph fastballs in the Spring Breakout game undoubtedly had their anxiety over that pick quelled as well.
We’re all Max Clark right now 😮
Seth Hernandez dials it up to 102 MPH on the very first pitch of the game! #SpringBreakout pic.twitter.com/hQ4kPXewop
— MLB (@MLB) March 20, 2026
Those same fans consider Davis, now in his fourth major league season, a bust because he’s never lived up to projections that had him as a consistent power hitter. But he brings a lot to the table defensively. He’s Skenes’s personal catcher and likely will catch Ashcraft and Chandler as well. Where he was drafted is irrelevant. It’s in the past and can’t be changed. All that matters is the kind of player he is now.
The eventual promotion of Griffin will slide Triolo over to third base, where he’s a defensive wizard. In the offseason, Cherington was rumored to have gone after Eugenio Suárez and Isaac Paredes, but couldn’t get a deal done. In any case, the Pirates can still have a winning record with Triolo at third base, despite him not providing the power one likes to see from a corner position. It’s a fallacy among fans that a team can’t be successful unless it has an All-Star at every position (although that certainly helps). The 1968 Detroit Tigers and 1983 Baltimore Orioles won the World Series with third basemen who hit in the low .200s without power.
If Hernandez doesn’t one day take Griffin’s spot as the No. 1 prospect in baseball, that honor might go to their No. 4 prospect, Edward Florentino, a combination of speed and power who the Pirates signed during the 2024 international signing period. Other highly regarded international signees with power potential include Esmerlyn Valdez, the South Atlantic League’s Most Valuable Player and the Arizona Fall League offensive player of the year, and Tony Blanco Jr., who wowed observers with his exit velocity during the Spring Breakout game. With the offseason acquisition of Jhostynxon Garcia, the system finally has some bats to go with the treasure trove of pitching prospects.
MY GOODNESS 😱@Pirates prospect Tony Blanco Jr. just sent this grand slam to space! #SpringBreakout pic.twitter.com/e3pA59Ktfl
— MLB (@MLB) March 21, 2026
If another disappointing season is in the cards, it could very well spell the end of the Cherington Era in Pittsburgh. As I write this, the Pirates have only their disastrous Opening Day performance under their belt. With the sting of that inglorious defeat still being felt by Pirates fans, this won’t be a popular opinion in Pittsburgh, but regardless of how the Pirates finish this year, Cherington has the organization in better shape than he found it. The clock was running, but he may have saved his neck with a buzzer beater.
