LAS VEGAS — On day one of baseball’s annual General Managers Meetings, crowds of media surrounded the presidents of the baseball operations for three big-market clubs — the Mets’ David Stearns, the Dodgers’ Andrew Friedman and the Phillies’ Dave Dombrowski.
Nearby, Pirates general manager Ben Cherington had a more low-key availability with reporters. He spent 10 minutes chatting with MLB.com, then took a few questions from two Minnesota reporters about the Twins recently hiring former Buccos skipper Derek Shelton for their managerial opening.
NJ Advance Media waited to get Cherington alone, then brought up something that Cherington didn’t know about the face of his franchise:
All-Star right-hander Paul Skenes, the 2024 NL Rookie of the Year and 2025 NL Cy Young favorite, has been telling Pirates teammates that he wants to play for the Yankees.
According to a Pirates teammate who recently spoke with NJ Advance Media, Skenes has “no confidence the Pirates ever are going to win” with him in Pittsburgh, and he’s “hoping for a trade” well before he can become a free agent after the 2029 season.
“Trust me, he wants to play for the Yankees,” the Skenes teammate said. “I’ve heard him say it multiple times.”
Cherington’s reaction?
“I do dismiss it, but I understand it,” the Pirates executive said Tuesday at The Cosmopolitan. “What we’re going to focus on is just how do we win games with him in a Pirates uniform.
“I have a ton of respect for the Yankees, but we’ll just focus on what we need to do.”
A year ago, when Skenes, a 23-year-old Orange County, California, native, was a Pirates rookie, he was hinting that he’d like to someday play for his hometown team, the Los Angeles Angels.
“Skenes grew up a big Angels fan,” a person with knowledge of the pitcher’s past intentions said. “He’s talked about going to the Arizona Fall League when he was 9 or 10 years old and getting Mike Trout’s autograph there. I used to think Anaheim was where Skenes wanted to go.”
Now it’s the Yankees, who unlike the Pirates and Angels, are annual contenders that will be able to afford Skenes at any price.
It’s easy to understand Skenes’ lack of faith in the Pirates. They have had only four winning seasons and three playoff teams in 33 years since Barry Bonds left as a free agent after the Braves beat them in Game 7 of the 1992 NLCS. Pittsburgh is 2-for-2 in finishing last in the NL Central with Skenes, going 76-86 in 2024 and 71-91 in 2025. And they consistently are one of the league’s lowest-spending teams.
“In a nice way, it’s really simple because what matters most to (Skenes) is what matters to us,” Cherington said. “Win more games. That’s the focus because that’s what is going to be most important to him. What probably gives us the best chance to keep him in Pittsburgh for longer is winning games, and that’s what we need to do anyway.
“So in a way it helps simplify it and focus it. My conversations with him, the only thing we talk about is winning and how to do that.”
Regardless, Skenes remaining with the Pirates even until he reaches free agency seems very improbable due to his future market value.
The Pirates, who have had one of the majors’ bottom-five payrolls 16 times in 19 seasons since owner Bob Nutting purchased the franchise in 2007, might feel like they have to move him before the 2028 season, his last before free agency. At that point, he could be in line for a $35 million salary.
If Skenes stays healthy and remains one of the best pitchers in the majors, he might get a record salary for a pitcher when he hits the open market, perhaps something in the 10-years-for-$500-million range.
If Pirates pitcher Mitch Keller isn’t traded this winter, his $16.4 million salary for 2026 will be a single-season franchise record.
Pirates center fielder Bryan Reynolds signed the richest contract in franchise history in April 2023, eight years for $106.75 million. It’s widely believed that the Pirates already are desperate to get that money off their books. Reynolds batted just .245 with 16 homers in 2025.
Opposing clubs frequently reach out to Cherington to find out if Skenes is available.
“The question gets asked and it’s always respectful,” Cherington said. “Teams have to ask the question, right? I suspect that won’t end, but the answer has been consistent.”
At this point, the Pirates are saying Skenes is off limits.
“He’s going to be a Pirate in 2026,” Cherington said.
He’ll still be cheap next season, probably only jumping from a $875,000 salary in 2025 to under $1 million because he’s not eligible for salary arbitration until 2027.
Skenes was the majors’ best bargain last season. He went 10-10 with an MLB-best 1.97 ERA with 216 strikeouts in 187 2/3 innings. The 6-foot-6, 260-pounder allowed one or no runs in 20 of his 32 starts and was 0-3 with three no-decisions when allowing two runs.
Skenes’ resume figures to improve Wednesday night when the Cy Young Awards are announced.
The Pirates have had only two winners, Vern Law in 1960 and Doug Drabek in 1990. Skenes is expected to become the third by beating out the two other finalists, Phillies left-hander Cristopher Sanchez and Dodgers right-hander Yoshinobu Yamamoto, whose World Series MVP performance won’t factor in voting that was turned in before postseason play.
“Paul wants to be great at what he does,” Cherington said. “He already is, and he’ll continue to push himself and he’ll continue to evolve as a pitcher. What he badly wants is to win.
“There are career considerations I’m sure that are important to him, but I think everything comes after winning.”
Cherington is hopeful that the Pirates will be a lot better in 2026, in part because ownership plans to increase payroll at least by a few million. It was around $87.6 million in 2025, ranking 27th among 30 clubs.
The Pirates have the makings of a standout rotation, so the extra money likely will spent on improving an offense that was last in runs and homers last season.
“I don’t know exactly where the final number will land, but I feel confident that we’ll have a little more flexibility than we’ve had in other offseasons,” Cherington said. “We’re going to do everything we can to put that to use through trades, free agency or a combination to add to the team as much as we can.”
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