Paul Skenes finally takes next step the Pirates needed in free agent process

The Pittsburgh Pirates are being uncharacteristically aggressive this offseason, with General Manager Ben Cherington working with a much bigger budget than years previous as he seemingly fights for his job. Luckily for Cherington, he has the reigning NL Cy Young Award winner in Paul Skenes on his roster, who is reportedly doing his part to help the organization in the free agent market.

Jason Mackey of the Pittsburgh Post Gazette reported that Skenes is willing and ready to take on the role of recruiter as the Pirates try to land some big name free agents this winter.

"Skenes, 23, volunteered his services to general manager Ben Cherington to contact potential free-agent targets around Major League Baseball and pitch to them the idea of playing for the Pirates — acting on his belief that Pittsburgh isn’t far from fielding a winner.
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Jason Mackey

Since the start of his second season with the Pirates, Skenes has become a very vocal leader in the clubhouse, and has not minced words when it comes to what team expectations should be moving forward.

“The focus needs to be winning a World Series in Pittsburgh,” Skenes said. “We haven’t done it since 1979. … That’s something we’re working to change from within the clubhouse. I know the organization is doing the same thing."

The shared belief between Cherington and Skenes is that the team is not far from being a contender. With that in mind, the team still needs to press forward with this alleged aggression this offseason. Having a player like Skenes to help recruit should make that process easier. Being that Skenes is a member of the MLB Players’ Association subcommittee, he has a wide net to cast based on connections he has with other players throughout the league.

Paul Skenes' art of the free agent pitch with Pirates

Cherington and ownership are fully aware that they need to act now to build a quality team around surging stars like Skenes, Konnor Griffin and Bubba Chandler. The pockets are open and the mindset seems to be completely different through the Winter Meetings. Although they didn't land Kyle Schwarber, the fact that they reportedly offered him a contract worth $120 million is enough to make any cheapskate blush.

Tyler Maher of SportsNet Pittsburgh reported on Cherington's three-pronged pitch to prospective free-agents.

"Cherington’s message is that “We aren’t that far away,” “It’s a fantastic place to be as a baseball person” and “It is an opportunity to do something different.”"

Tyler Maher

It may seem like an uphill battle trying to buck the nasty heritage that has followed the Pirates in the 21st century, but this is a good pitch. Surely there are players out there who have 'Dodgers Fatigue' and want to be a part of something new and possibly exciting. There is no doubt that the Pirates, as a whole, are in a bit of a downswing period, but Pittsburgh is an excellent place to be a professional baseball player, with an incredible fan culture that is yearning for a winner.

Aside from his incredible work on the mound, Skenes brings a winning and motivated attitude to the team's clubhouse. For far too long, Pittsburgh has lacked a player of Skenes' caliber coupled with the leadership qualities and vision that he possesses.

There were plenty of rumors that Skenes wanted out of Pittsburgh this past season, and plenty more that the organization would be willing to trade him, but Skenes made it clear to all that he wants to be is a Pirate.

"The goal is to win, and the goal is to win in Pittsburgh," Skenes said this winter.

Seemingly from day one, Skenes has been passionate about trying to bring back a winning culture to Pittsburgh. With that passion, he can help to recruit the top talent in free agency. As humble as he is, it wouldn't hurt to mention to prospective players that they would get to play alongside one of the best pitchers in baseball and with one of the best rotations overall. If they can land one big offensive threat this offseason, more will want to follow. This team is young and hungry, while this city is passionate and wanting more out of their ball club.

Mackey noted that Skene's dedication to Pittsburgh has been outstanding since joining the team.

"It backs what I’ve known about Skenes since he signed — that he genuinely loves Pittsburgh, for its humbleness, his teammates, the way he’s able to live here and its blue-collar background, and that he sees the Pirates as a sleeping giant within MLB."

Jason Mackey

Skenes will continue to be an asset both off and on the field for the Pirates' organization. The 23-year-old All-Star is heavily involved in the Pittsburgh community, as well as the military and first responder community via the Gary Sinise Foundation. Skenes was selected as the Pirates' Roberto Clemente Award nominee in 2025.

Having one of the best players in the game who just also happens to be one of the best human beings in baseball should be a selling point on its own. Regardless of what he's able to accomplish as a recruiter, Skenes is taking the winning attitude into next season.

“I think it’s going to be better next year, but talk is cheap. We have to show up and do it. I have confidence we’re going to and that we’re going to get better," Skenes said. "But there’s a long way to go. I’m excited for the challenge.”