Dealing at the deadline: Pirates place trust in GM Ben Cherington to make right trades

Mitch Keller was flattered to see his name pop up in trade rumors, given his roller-coaster career before blossoming into an All-Star this season.

A year ago, the Pittsburgh Pirates right-hander had been demoted to the bullpen. Now, there’s a hefty price tag on Keller’s head for any contender that wants to acquire him.

Even so, Keller was hoping Friday night’s start wasn’t his last for the Pirates. He made it clear he doesn’t want to be dealt at the deadline.

“I definitely want to be here for the rest of my career,” Keller told the Tribune-Review. “Being drafted here and being homegrown, I guess, is kind of special. At the start of the year, we didn’t have this many young guys, but now we have I-don’t-know-how-many prospects, which is really cool to see. To be a part of that would be awesome. We have a lot of pieces. It’s cool to see the future players are here, and I would love to be a part of it.”

The Pirates were expected to be sellers before Tuesday’s 6 p.m. trade deadline, and they started the process Thursday by sending first baseman Carlos Santana to the Milwaukee Brewers for 18-year-old shortstop prospect Jhonny Severino in what could be the first of multiple moves.

While that deal gave some fans the impression Pirates general manger Ben Cherington’s rebuilding project isn’t over, players weren’t surprised to see Santana go because he’s on a one-year contract and is viewed as a rental for a contender such as the NL Central-leading Brewers.

The question is, how far is Cherington is willing to go?

Pirates players are putting blind faith in the front office to make moves that add young talent without subtracting too much from the core of their lineup or pitching staff from a team that was in first place in mid-June before sinking to last place over the past six weeks.

“We fully trust in what he’s doing,” Keller said of Cherington. “You can see the vision, see what he’s applying and how the team’s shaping up and how our minor-league depth is going. To have trust in that is huge, and we trust every move he’s making.”

Cherington has had mixed success at the trade deadline, swinging deals for the Pirates that returned a power-hitting outfielder, a versatile middle infielder and a high-leverage reliever — all with years of club control. He also has several misses, including trading a lefty starter and a righty reliever who have since become All-Stars.

Pirates manager Derek Shelton credited Cherington for how he has handled trade rumors, whether it’s involving veterans with value such as Santana and 43-year-old left-hander Rich Hill or attractive All-Stars such as Keller and closer David Bednar.

“I think Ben does a good job and has done a really good job all four years we’ve been here with guys that either it’s been speculated or guys that may be part of trade talks that he gives them a head’s up and he’s pretty open and transparent with as much information as he can give,” Shelton said. “Once you get into the game, people are traded now. It’s not like 20 years ago, where you never saw people moving. It’s commonplace.

“With this group of players, the more they grow up with it, they know the deadline is there. They know about the possibility that things could happen. So there’s no getting in front of them and having a speech about this is where it’s at. It’s more one-off conversations.”

Trading an All-Star at the deadline proved to be one of Cherington’s shrewdest deals. He sold high on Adam Frazier, who started at second base for the National League in the 2021 Midsummer Classic, was leading the majors in hits (125) and ranked second in the NL in batting (.324).

Frazier became only the third player in the modern era traded midseason while leading the majors in hits when the Pirates sent him to San Diego on July 26, 2021, for infielder Tucupita Marcano, right-hander Michell Miliano and outfielder Jack Suwinski. They even gave the Padres $1.4 million to gain access to a better pool of prospects, which proved a wise investment for Suwinski alone.

Suwinski required the fewest at-bats to reach 40 home runs in Pirates history. After starting the 2022 season at Double-A Altoona, Suwinski hit 19 homers as a rookie. He’s leading the Pirates with 21 homers and 52 RBIs through 90 games this season.

Marcano started 44 games at shortstop this season before injuring his knee Monday. He was batting .233/.276/.356 with 12 doubles, two triples, three homers and 18 RBIs in 75 games this season.

Frazier never replicated his success at the plate. He batted .267 in 57 games with the Padres before being traded to Seattle, where he hit .238 with 22 doubles and 42 RBIs last season. Frazier signed with Baltimore, where he’s batting .241 with 14 doubles and a career-best 12 home runs.

On that same day, Cherington made one of his worst moves. He has since expressed regret over sending right-handed reliever Clay Holmes to the New York Yankees on July 26, 2021, for minor leaguers Diego Castillo and Hoy Park.

Where Castillo and Park were utility players for the Pirates — both are now playing in the minors for other organizations — Holmes blossomed into an All-Star closer who has a 2.24 ERA, 34 saves and is averaging 10.1 strikeouts per nine innings in two-plus seasons for the Yankees.

“We spend a lot of time thinking about it,” Cherington said last July, before the Yankees visited PNC Park. “Of course you look back and review everything you do. What’s happened since, and if a player performs much differently — whether that’s a player that’s here or a player that’s not here anymore — than we were expecting, then we’ve got to go look at that. What’s the information we were relying on at the time, and if we were off in our estimations, why was that? What can we learn from it?

“I think that process needs to happen all the time, and we’re constantly reviewing these things. I think you have to do that and be critical of yourself and learn as much as you can and then not have that stop you from pursuing more things, because the quickest way, probably, to stop getting better is to stop doing stuff. We’re going to have to explore opportunities and not be locked up by something that happened in the past that didn’t work out exactly as we might have expected. We can look at both sides of that, so yeah. We think a lot about all of them and review all of them and learn from as much as we can and then take that learning and go find the next one, try to execute.”

Two days after the Holmes trade, Cherington dealt lefty Tyler Anderson to the Seattle Mariners for a pair of minor leaguers, catcher Carter Bins and 17-year-old right-hander Joaquin Tejada.

Anderson, who was on a one-year contract, is 20-7 with a 3.48 ERA and 1.19 WHIP the past two seasons and was an All-Star for the Los Angeles Dodgers last year. Bins has been injured most of the season, while Tejada is a reliever in the Florida Complex League.

Cherington’s worst deal begat one of his best, this time with another New York trade partner: The Pirates sent designated hitter Daniel Vogelbach to the Mets last July for right-handed reliever Colin Holderman.

Being dealt at the deadline was a surprise to Holderman, who thought he was being sent to Triple-A. To go from a contender to a last-place team provided a new opportunity for Holderman, as he left a pressure-packed bullpen for one that welcomed the sinkerballer.

Where Vogelbach has 13 home runs and 55 RBIs in 127 games for the Mets, Holderman has developed into a reliever who has thrived in the back-end of the bullpen to the point that a handful of teams have expressed interest in trading for him. The constant comparisons between himself and Vogelbach is part of the reason he stopped using Twitter.

“I tried not to look but every time something would happen, Twitter would go crazy and I’d get tagged in all that stuff,” Holderman said. “I didn’t want to see what was going on. I just wanted to focus on myself here in Pittsburgh. Obviously, going into it I wanted to be the better end of the trade. I wanted to give Pittsburgh the better end of the deal. Hopefully, I can do that going forward.

“I know there are some teams making a postseason push that are in need of relievers that have called … but I know Ben wants to keep me here. We’ve had conversations. I would love to stay here. I think we can do something special.”

That leads us to weigh the Art Vandelay question: Are the Pirates exporting or importing at the trade deadline?

To Shelton, just because they are viewed as sellers doesn’t mean they aren’t seeking something of value in return. He used Holderman and another deadline deal last year — sending lefty starter Jose Quintana and righty reliever Chris Stratton to the St. Louis Cardinals for righty Johan Oviedo and first-base prospect Malcom Nunez — as an example of a trade that will pay future dividends.

Perhaps no trade has paid off as much for the Pirates as when the previous front office dealt reliever Tony Watson to the Los Angeles Dodgers for a then-teenage shortstop named Oneil Cruz in July 2017. Six years later, Cruz was on the cusp of becoming a star before a fractured left ankle caused him to miss most of this season.

They have their fingers crossed for a bountiful return on lottery tickets like Severino.

“That’s importing for us,” Shelton said. “There’s a different way of looking at it, if you’re importing to add specific things to your club instead of generally looking for as much talent as you can acquire. Right now, we’re still looking at it as like, ‘We’re importing talent.’ Sometimes, that talent might be a little further away, but we’ve got a couple guys that we got when they were 18 years old that are in that room right now, which is really important.”