'It's time to start getting better': Pirates GM Ben Cherington drives home new expectations

Before Ben Cherington could contemplate what type of expectations he has for the Pittsburgh Pirates this season, he first recalled what it was like to endure the brutal past three years as general manager.

After compiling the worst record in baseball during the pandemic-shortened 2020 season, the Pirates made the decision to trade away some of their top major league talent for prospects even though it would lead to difficult days in the short term. What followed was their first back-to-back 100-loss seasons since the mid-1950s, nights that took a toll on the man in charge of assembling patchwork teams with a mix of waiver claims and young prospects.

“It’s hard, no doubt, going through seasons like that,” Cherington said by phone Friday from the back fields at Pirate City in Bradenton, Fla. “When you leave the ballpark after a loss, I don’t care what the expectations are, I don’t care where you are in team development or whatever, that’s a hard drive home.”

Disappointed by the results, the Pirates realized that it was time for a step forward after taking two steps backward. Cherington got the green light to spend $30 million in free agency in the offseason, signing six veterans to supplement the young core, that has the Pirates talking about becoming more competitive in 2023.

“It’s time to start getting better,” Cherington said. “It’s a different time in our evolution.”

It’s a time that reminds Pirates chairman Bob Nutting of when they followed a 105-loss season in 2010 by going 72-90 in 2011 and 79-83 in 2012 before ending a two-decade drought from winning seasons by earning three consecutive wild-card berths. That’s the hope Nutting offers to Pirates fans who have endured 100 more defeats than victories over the past three years: Better days are coming, if they are willing to practice patience for the plan to play out.

“I can’t wait to see this team on the field right now,” Nutting told the Tribune-Review last month at LECOM Park. “There’s a young core we had a chance to solidify, add a lot of talent at the lower level, watched that group develop. Now, there’s pressure and competition coming up behind them and to be able to add on top of that some of the veteran presences that we have, that’s exactly what we’ve been talking about doing. … It’s critically important that we stay to the plan and process because I’ve seen it work before, and I think we’re going to see it work this year.”

Improvement isn’t a hard sell. After finishing last in the NL Central three consecutive seasons and tied for fourth last season, the Pirates have nowhere to go but up. Mind you, no one in the organization is talking about going from worst to first or even mentioning making the playoffs.

That begs the question: How much better?

Signing five-time All-Star and 2013 NL MVP Andrew McCutchen, their best player of the PNC Park era, piqued the interest of frustrated fans. Adding Carlos Santana and Ji-Man Choi improved first base, 43-year-old lefty Rich Hill gives the starting rotation a veteran voice and defensive whiz Austin Hedges solidifies the starting job at catcher.

Can the Pirates duplicate what the Baltimore Orioles did, increasing their winning percentage by 19.1% in going from 52-110 in 2021 to 83-79 last season? Orioles manager Brandon Hyde experienced a 24-game improvement with the Chicago Cubs in 2015, who followed a 73-win season by going 97-65 and beating the Pirates in the NL wild card.

“In Chicago, we got way better in ‘15 — we won 97 games — but we didn’t see that coming. Last year, we were supposed to win 50-something games and won 83. Nobody saw that coming, either,” Hyde said at Grapefruit League media day last month in Dunedin, Fla. “The pitching is the biggest thing. We were able to win games last year because we pitched. Being able to pitch to stay in games, especially in our division, is something we couldn’t do before we did last year. You’ve got to get lucky, too.”

Cherington knows that it will take some luck, but he prefers to put his energy toward positive productivity and incremental improvement. That’s why he gives manager Derek Shelton credit for keeping the team’s focus on playing with full effort, no matter the results. The Pirates have had their share of embarrassing moments, from Will Craig’s rundown to Rodolfo Castro’s phone popping out of his pocket to Ke’Bryan Hayes eating sunflower seeds as a run scored, but Shelton prides himself on his team always playing hard.

“He has been through difficult days, as we all have,” Cherington said. “The thing that I respect about him, as much as anything, is his energy to keep fighting and keep coming back the next day and finding ways to get better. He’s just been dogged since the day he got the job about improving: improving himself, improving for us. We talk about it a lot. We need to help each other get better, keep getting better and he’s been entirely focused on that. I really respect that.”

But the Pirates aren’t allowing room for moral victories, not after slashing payroll and being accused of tanking by the MLBPA. Ownership has promised progress, and a sign that even the players are becoming restless came when All-Star outfielder Bryan Reynolds requested a trade after contract extension talks came to a $50 million impasse.

There is promise, especially now that the trade acquisitions and draft picks are elevating through the system. The Joe Musgrove deal brought All-Star closer David Bednar and a top prospect in catcher Endy Rodriguez. The Jameson Taillon trade returned right-handed starter Roansy Contreras and outfielder Canaan Smith-Njigba, a spring training standout. The Adam Frazier trade got slugger Jack Suwinski, who hit 19 homers as a rookie. Former first-round picks Quinn Priester, Nick Gonzales and Henry Davis could make their major league debuts sometime this summer.

With Reynolds, third baseman Ke’Bryan Hayes and right-handers Mitch Keller and JT Brubaker, the Pirates appear to have a talented young core who believes their best days are ahead of them. They are counting on the veteran additions to relieve some of the pressure by providing leadership and depth to the lineup.

If that places more pressure on Cherington, he’s not sweating it.

“I don’t feel any different. I feel the same amount of pressure,” Cherington said. “There’s pressure in this job from the day you take it. I fully understand and accept the responsibility that I have. I’m the leader of baseball operations. Ultimately, we’re responsible for putting the team on the field and so therefore I’m accountable for the performance. There’s pressure that comes along with that.

“Personally, I don’t feel that any more pressure today than the day I got the job. Others may feel or believe that it’s different, and I respect that. That’s part of the territory. I don’t feel that way. I don’t think Shelty feels any more today than the day he got the job. We’re too busy trying to figure it out. We’re too busy trying to figure out what’s today bringing and what problems we need to solve. That’s where our heads are.”

Cherington adds that he and his baseball operations and coaching staff constantly remind each other: For every challenge that comes with rebuilding the Pirates into a contender, they get to do this. It’s a test of their attention to detail, skill and creativity to build from the bottom a team that goes from competitive to contender to champion.

“We are privileged to do this, that we get to be the people who have a chance to do something about it, have a chance to make improvements. That’s an incredible honor. It’s a gift, and I’m grateful for it every day,” Cherington said. “And, in Pittsburgh, it really does matter because the Pirates matter so much to our fans, to the city, to Western Pennsylvania, to baseball. I think it’s important that baseball thrives in Pittsburgh. I think it’s important to Major League Baseball that baseball thrives in Pittsburgh. All that stuff helps get you through and keeps you energized during what were difficult times.”

And hard drives home that he hopes become better with every game.