Three questions facing Cherington upon entering pivotal offseason

While the most basic, and probably best, way to evaluate the 2023 Pirates is to look at their overall body of work, an argument could be made that it is beneficial to look at the season in three chapters.

April was by far one of the team's best months in years. They started at 20-8, and save for a few injuries, just about everything that could go right did. The other 134 games told a drastically different story. During the final 67 games, the Pirates played winning baseball, going 35-32, which is the same winning percentage of the playoff-bound Marlins. That first stretch of 67 games was a polar opposite, and they went 21-46, which was barely a better winning percentage than the 112-loss Athletics.

The Pirates are banking on that final chapter being the true indicator of where they are as a franchise and why they believe they could make the leap to contention in 2024. Had that middle section not happened, though, they could have theoretically been in the mix in 2023. And for that, Ben Cherington took responsibility.

"Some of it was as simple as we weren’t good enough," Cherington said in his end of season availability with local media at PNC Park Tuesday. "My job, ultimately, of building the roster to be deep enough, strong enough to get through a year successfully, withstand the harder parts of the schedule. Every team is going to go through them. The season showed us that we weren’t there yet. We needed to keep getting better as a team, as an overall roster. That’s ultimately on me."

The Pirates are entering a pivotal offseason, one where players and coaches have made clear that they are shooting for the playoffs in 2024. They won 14 more games in 2023 and 2022, which is more than half of the expected gap between 100 losses and October baseball, but it was also the easier half.

"Going from the 60s to the 70s is not easy, but the next step, I do believe is harder," Cherington said. "Winning a single game in the Major Leagues is hard. Lots of things have to go well to win a single game. So, if you’re talking about that next step, we need to add to where we got to this year. It’s not going to be easy. It’s going to require all of us to dig even deeper and be better in every kind of way."

There will be plenty of questions that need to be answered this winter for the Pirates to take that next step. For now, there are three larger ones.

WHAT'S THE FOCUS THIS WINTER?

During the 39-minute session, Cherington hinted that the bullpen is an area that will see additions this year, as well as the position player core. While he offered no specifics for the latter, first base is the most glaring hole currently on the offensive side.

"We have the resources we need to get better and to compete and contend," Cherington said. "I’m confident in that."

But if one thing was clear about the Pirates' offseason shopping list, it's starting pitching.

"You want to walk into spring training feeling like you have 10," Cherington said. "I don’t think I can tell you right now we have 10. I also think it’s within our reach between now and February to get to the point where we can say we have 10. Whether that’s external additions. Whether that’s continued growth from guys who are already here or just return to health. I think if we do our jobs well enough, we can get to that point in February to feel like we can say we have 10. We’re not there right now."

The Pirates operated effectively with a two-man rotation for most of the final weeks of the season, leaning on Mitch Keller and Johan Oviedo and then a series of spot starts and openers from there. Quinn Priester, Luis Ortiz, Andre Jackson and Bailey Falter were often used as a starter or bulk guy in that time. Roansy Contreras is still viewed as a starter option. Max Kranick and Jackson Wolf have a bit of major-league experience but finished the season in the minors. JT Brubaker and Mike Burrows will start the year on the injured list, but should ready midseason. There are also some prospects who could make their debuts next year, like Paul Skenes and Jared Jones.

But if the prospects and injured pitchers are off the table for opening day, the Pirates don't really have 10 starters avaible, even if swing guys like Jackson, Falter and Kranick are all considered and Contreras bounces back.

The past three winters, starting pitcher additions have been almost exclusively one-year free agents. While there have been a few clunkers -- Trevor Cahill and Derek Holland come to mind -- the team has generally had success with reclemation projects. Tyler Anderson went from a swingman to an All-Star, José Quintana got his career back on track and Vince Velasquez looked really good up until being injured. Those pitchers were low-risk, low-cost signings, though. Cherington has yet to sign a free agent to a guaranteed multi-year deal. Expanding the range of available pitchers could potentially bring in someone with a higher floor and/or a higher ceiling.

While the team hasn't gotten too deep yet into their offseason planning, it does sound like an expanded search is on the table.

"We need to get deeper into our planning to figure out exactly the targets that make sense for us," Cherington said. "It’s a different point in time, though. I think that means we can be open to maybe a different type of target. We’ll just have to see. Again, don’t want to lean on free agency exclusively as the answer to all of the things we want to do. I think we need to cast a wide net."

WHO IS COMING BACK?

There's been plenty of stated desire -- both from the Pirates and Andrew McCutchen -- for the two sides to re-up his contract this winter. That certainly is the expectation, and Cherington and McCutchen will talk in the coming days.

"I think the first thing I would like to do is sit down with him -- again, let the season get past -- and listen to what does he want," Cherington said. "I would like to get his feedback on the team, too. Not just on him, but the team. Listen and learn and get a better picture [of how he] wants to envision things going forward. We can share the same. See where it goes from there. Certainly interested in him wearing a Pirates uniform next year. That would be a great outcome. But I think we owe it to him to sit down and have a conversation first and listen."

While McCutchen will almost certainly return, there are a couple question marks up in the air when it comes to the team's more veteran players. Both Mitch Keller and David Bednar are going to be arbitration-eligible this winter. Keller restated his desire this final week of the season to work out a long-term deal with the Pirates, while Bednar told me at the All-Star Game he loves Pittsburgh and hopes to stay. Cherington didn't offer much about a potential Keller extension Tuesday, but both sides will have to talk at length this winter anyway if they want to avoid arbitration.

When it comes to the younger players, the message to Henry Davis in his exit interview was to prepare this winter as a catcher and that he will be part of pitchers and catchers next year. Davis did plenty of behind-the-scenes work to improve his catching, but did not make a start in the majors and had catcher work taken off his plate late in the year when he was recovering from a hand injury.

While he almost exclusively played right field in the majors, the team hasn't closed the door on him catching alongside Endy Rodríguez.

"We believe they can do it. We don't need to make decisions right now on who's on the team, what role guys [are going to play]," Cherington said. "We have time to figure that out. Things will happen this offseason. We just don't have to make those decisions right now. What we have to decide right now, in fairness to players, is what the training looks like this offseason. That's what the messaging is focused on catching."

That leaves the coaching staff. It's already known that Derek Shelton, Oscar Marin and Andy Haines will return in 2024. Bench coach Don Kelly's name has popped up in managerial searches the past few winters, so it's reasonable to assume he will get some consideration again this offseason.

"If I was somewhere else and going through a search, he would be someone who would have the attributes you're looking for," Cherington said. "He's got a really strong combination of traits, starting with his level of integrity and the values he walks into the park with every day, gives him the opportunity to earn trust with everybody in that room."

Assuming Kelly is back, it doesn't sound like there is going to be much turnover on the coaching staff. Shelton and Cherington are going to sit down soon to go over the rest of the coaching staff to see if they need to add or if there is an area they could approve, but by and large, expect continuity in the coaching staff.

"That’s my expectation," Cherington said. "Shelty and I will have a chance to go through that exercise. I think it’s important to talk about how we get better. But we believe in the group. Expectation is that the group is gonna continue to work together and continue to help each other find a way to get better."

WHAT DO YOU TAKE AWAY FROM THIS YEAR?

It's been said for years, but if the Pirates were going to be elevated to contenders, it's going to have to be driven by internal improvement and young players getting better. According to Baseball Reference, the Pirates were the youngest team in the National League this year (27.6 years on average). That number could very well decrease next year, given that there should be more prospects on the way.

"We have more players coming, and we need to do our jobs to support that," Cherington said. "That’s always going to be a key part of it. We’ll be in a position to add to the team, whatever the avenues are. It’s not going to be a single avenue, whether it’s trades, free agency, waivers, Rule 5. We shouldn’t be overlooking any potential avenue, but confident that we have the resources we need to make the team better this offseason.

There will be competition this spring for several spots, but the core of next year's lineup is already in the clubhouse. If the Pirates will compete next year, it will have to be because they took the next step, first are foremost.

So what is Cherington hopes those rookies took from their first taste of the majors?

"They kinda said it. We didn’t have to say anything," Cherington said. "It was very clear listening to our players, particularly the young group, that the major league game’s hard. It’s faster. Adjustments get made faster by the opposition. Stadium’s are louder, all of that. It’s a different experience than playing in Altoona or Indy. To some extent, no matter how much we try to create environments in the minor leagues to test that, there’s nothing quite like experiencing it. One might be working on the same things in Indy as they are in Pittsburgh in terms of skills and things like that. But applying that in a major league game does feel different.

"More than anything, we had a lot of young players get to do that this year. In a lot of cases, have enough time in the big leagues to actually already make some adjustments inside the major league experience. Not just a cup of coffee but enough of a runway to actually go through some adjustments. I think our group is leaving here with a pretty clear mind of, ‘The game’s hard. It’s faster at the major league level. This is a thing I need to get better at.’ Then it’s up to us to help them get better at it this offseason and come into spring training in a better spot."