Column | Pirates need new management after another season flying at half-mast

The Pirates’ 2024 season officially came to a close on Sunday with a 6-4 loss to the New York Yankees, ending a season that saw them eliminated from postseason contention weeks ago. 

It’s the Pirates’ sixth straight losing season, ninth without a playoff appearance and 28th losing season since 1992 — the last time they claimed a division pennant. 

For decades, so many Pirates teams have been hampered by under-budget rosters and a general lack of talent. The seasons almost always ended the way they were supposed to — well below the playoff line. This year’s team was an exception to that rule, one that truly had the ability to bring Buctober back to the North Shore. 

There was serious hope and promise coming into this season. The 2023 campaign saw the Pirates finish the year 76-86, a 14-win improvement from back-to-back 100-loss seasons. Despite injuries, depth problems and selling at the trade deadline, last year’s Pirates showed a lot of fight.

Things were only supposed to get better. Reinforcements on nearly all fronts had set the Pirates up for their first truly competitive season in Ben Cherington’s time as general manager. 

Talented rookies like Jared Jones were ready to make an impact, Andrew McCutchen signed on for another year, a healthy Oneil Cruz was ready to play, Aroldis Chapman came in free agency and another year of development for the team’s youth was supposed to signify the end of a rebuild in Pittsburgh. 

The crown jewel of this new crop was Paul Skenes, who put together a historic rookie season with a 1.96 ERA, a 0.947 WHIP and 170 strikeouts. He became the first pitcher in MLB’s history to have a sub-2.20 ERA and 150+ strikeouts in his first 23 starts. It was a season that earned him an all-star nod and is set to make a strong case for NL Rookie of the Year. 

The team’s best first half in years had Cherington ready to make moves focusing on the present for the first time as general manager. Sitting above .500 on deadline day, Cherington brought in three names to bolster the roster. 

Two months later, the Pirates sit at 76-86 again — no improvement from last year. Where, oh where, did things go wrong? 

From Aug. 4 to 14, the Pirates went on a ten-game losing streak that tanked their season and plunged them under .500. They dropped several key matchups, including sweeps at the hands of Arizona and San Diego, two teams that they were in direct competition with for a wild card spot. 

This losing streak was simply a microcosm of everything wrong with the organization and, in particular, manager Derek Shelton. 

Through that streak, Shelton refused to correct his course when the same problem continued to happen. Two of his most trusted relievers, Colin Holderman and David Bednar, were clearly struggling. Bednar had been suffering all year, while Holderman was suffering a crash of epic proportions in late July and early August. 

There’s trusting your guys and then there’s trusting your eyes. Both men, and Bednar in particular, had proven to Shelton that he had no reason to trust them in high-leverage situations. Still, Shelton dug his head in the sand. He refused to remove either one from the roles he had given them. As a result, those two combined for an 0-6 record, four blown saves and 16 total earned runs in a two-week span. It was a season killer. 

Shelton’s way of handling position players was equally suspect. When the games still mattered, Shelton managed his team like a little league roster, balancing out playing time even when performance dictated the opposite should occur. 

He abandoned that philosophy when the games no longer mattered, favoring veterans over young prospects that would have benefited from playing time. 

Cherington has previously said that Shelton’s job is safe, but take this with a big grain of salt,

because this is the same guy who stated that Cruz would remain at shortstop for the Pirates, then eight days later announced his new position would be center field. 

A genuine props to him for trying to make this roster competitive at the deadline, but perhaps one of the most dangerous things for this organization is whenever Cherington picks up the phone to call another general manager. 

He sent off high-rising hitting prospect Charles McAdoo to Toronto for Isiah Kiner-Falefa. This trade could have worked out, but only if the Pirates got out of their own way. Kiner-Falefa’s most prized trait is his versatility, but the team has since clipped his wings and stapled him to the shortstop role — arguably his weakest defensive position. 

Bryan De La Cruz, who came over from Miami, failed to deliver any power in his bat and continued his work as one of the worst defensive outfielders in baseball. Jalen Beeks didn’t fare any better, failing to assist an ailing Pirates bullpen. By contrast, Luis Peralta, who the Pirates gave up to get Beeks, got his career off to a dominant start in Colorado. 

But losing trades isn’t at all new to Cherington. Take a few minutes and scroll through Cherington’s trade history, especially in the early years. It’s an absolute doozy. 

This guy getting repeatedly swindled is just part of the reason this franchise is in year five of his rebuild and still well below the playoff line. That’s not even to mention his repeated whiffs in free agency and his absurd dedication to controversial pitcher Domingo Germán, who did nothing but provide the organization PR nightmares. 

Rebuilds in MLB do not work this way. Detroit was 66-96 two years ago. Kansas City was 56-106 last year. Both are now playoff teams. 

It is simply unacceptable for this organization to fall this far behind despite so many more years sunk into efforts to be competitive. This regime has had five years to get somewhere — and it hasn’t. The very top of Pirates brass needs to step in. Enough is enough.