Analysis: With Ben Cherington, Derek Shelton on hot seat, Pirates must find ways to win

In a pitch to pacify a frustrated fan base, Pittsburgh Pirates president Travis Williams acknowledged their passion was evident “because we’re not winning and have expectations of winning” before assuring everyone about the club’s commitment to want to win.

To prove how close the Pirates are to winning, Williams pointed to the positives: They entered August two games over .500 and 2½ games back in the wild-card race before enduring an epic collapse. That pretty much pinned blame on general manager Ben Cherington for his trade deadline deals and manager Derek Shelton for a 10-game losing streak.

“What it tells me is, we’ve got to figure out a way to win the games that we didn’t win in August,” Williams said during a Q&A session with fans last month at PiratesFest. “And that’s on all of us in the organization, from myself to Ben to Derek to lots of other people that are here today and throughout the entire organization.

“That’s not for lack of commitment or desire to win whatsoever. That’s from the top all the way down to the bottom of the organization. We’re absolutely committed to win. What we need to do is find a way to win. That’s what we’re working on.”

What Cherington and Shelton are working on are hot seats that will only get hotter if they don’t get off to a fast start and find ways to win close games. As much as some fans fueled their anger at Bob Nutting to sell the team, the Pirates chairman has invested in long-term contracts with Gold Glove third baseman Ke’Bryan Hayes and All-Stars in outfielder Bryan Reynolds and pitcher Mitch Keller and a then-record signing bonus in 2023 No. 1 overall pick Paul Skenes, who won NL Rookie of the Year honors last season.

Even so, the Pirates have a projected Opening Day payroll of $82.2 million, which ranks 26th out of 30 MLB teams. They made one offseason trade, acquiring first baseman Spencer Horwitz, and have signed five free agents for a total of $14.7 million.

That explains why the most pointed questions at PiratesFest were directed at Cherington. That included asking if he was on the hot seat to produce a winning team.

“Yeah, the hot seat,” Cherington said, “every minute of every day since November 2019.”

That’s not quite true. Cherington and Shelton were afforded a prolonged honeymoon phase that started with producing the worst record in baseball (19-41) in the pandemic-shortened 2020 season and the tear-down trades involving Josh Bell, Starling Marte, Joe Musgrove and Jameson Taillon. Fans endured the rebuilding process that followed, with back-to-back 100-loss seasons for the first time since the 1950s.

There was optimism in 2023, as Andrew McCutchen received a roaring ovation in his return after five years and Shelton received a contract extension amid a 14-7 start. The Pirates won 20 of their first 29 games for the best record in the National League at the end of April, only to go 8-18 in May. Still, they spent 33 days in first place in the NL Central and went 29-28 over the final two months of the season.

There was more positivity when the Pirates started last season with a sweep at Miami, then took two of three at Washington and in the first home series against Baltimore before losing nine of 12 during a stretch in April. But they bounced back, going 14-12 in June and 15-10 in July and were buyers at the trade deadline, addressing needs by acquiring left-handed reliever Jalen Beeks, right fielder Bryan De La Cruz, middle infielder Isiah Kiner-Falefa and hitting prospects in Billy Cook and Nick Yorke who can play the infield and outfield.

Where Beeks and De La Cruz bombed, Kiner-Falefa’s arrival allowed the Pirates to move Oneil Cruz to center field and Cook and Yorke showed they could hit in September cameos. No wonder Cherington had to defend himself by saying he has “zero fear of making trades.”

“You look back at July, for example, and that combination of trades and we can already see that there’s some that didn’t work out exactly perfectly the way we wanted to in August and September,” Cherington said. “That combination of trades very clearly pushed the Pirates forward as we go into 2025. We’re a stronger organization than we were in July because of the combination of those trades, so we’re going to keep doing that.”

That’s one way to spin an 8-19 August that included a 10-game losing streak and saw the Pirates plummet into last place. Shelton pointed to the sold-out series against the Philadelphia Phillies in late July as proof of the excitement that comes with being in playoff contention. But the bottom dropped out a few weeks later with four one-run losses in a six-game homestand against Arizona and San Diego.

“It’s my job to make that our connection with our player group is so strong that we figure out a way to get through that tough stretch and we don’t lose eight, nine, 10 games in a row,” Shelton said. “Maybe we go .500 in that stretch and we’re in a good spot. That’s my responsibility. That’s something that I probably didn’t do a good enough job of last year.”

Probably? Shelton has overseen 10-game losing streaks in each of the past two seasons. Yet he received a vote of confidence from Cherington last September, who said the coaching staff “works as hard as any in baseball, and I know cares as much as any in baseball.”

Caring isn’t the same as winning, despite Shelton’s declaration that “all I think about is winning.” It’s telling that the Pirates overhauled both their baseball operations and coaching staffs this offseason, as Cherington hired new directors for the farm system, pro and international scouting and research and development departments and Shelton hired a new hitting coach, bullpen coach and brought in 76-year-old Brent Strom as assistant pitching coach.

That could be viewed as a sign of Nutting’s commitment to winning or his clear dissatisfaction with the Pirates’ progress.

Either way, the Pirates know their window to win opened when Skenes made his major league debut last May. His historically dominant rookie season proved that their odds increase every time Skenes takes the mound, and it’s vital that they capitalize during his tenure.

But there is little margin for error, whether that comes in the form of injuries, ineffectiveness or a lack of focus on the fundamentals that have cost the Pirates too many close games in the Cherington/Shelton era.

McCutchen cited the Pirates’ inconsistency in executing the details of small ball — from laying down bunts to move runners over to driving in runners on third base to staying ahead in counts — that cost them in close games as an area of improvement that could change a season.

“I sit back and watch the game, and there’s so many of those instances where it’s like, if we would’ve done that, that game would’ve been different. If we would’ve got that done, that game would’ve been different. We would’ve won that game,” McCutchen said. “Bro, I’m talking 15-20 games. Quite frankly, you could maybe round up to 30. If you win 15-20 of those 30, you’re in a different position. So that’s how I look at it. It’s not like 15 to 20 to 30 of those games we just got flat-out beat. It was like no, we were in it, we didn’t execute, we lost. And it’s like, ‘OK, what do we need to do as a whole, man?’ We need to execute. Just execute.”

This season will determine the difference between wanting to win and finding a way to win, one that will require the Pirates to start fast and finish with a flourish. Cherington and Shelton will keep their fingers crossed that the Pirates can catch fire before their seats do.