What Jameson Taillon's trajectory with Cubs says about their offseason approach to pitching

Right-hander Jameson Taillon chose a spot on the field-side of the dugout railing before the Cubs’ last road game of the regular season. It improved his perception, he explained. The rain had just let up. And standing there, he could survey most of Philadelphia's Citizens Bank Park as he reflected on the season.

“Obviously, we didn't do what we wanted to do, we didn't get to where we wanted to get,” he said in a conversation with the Sun-Times. “But I think it's important to still try to find a way for everyone, individually, to take something positive into the offseason.”

Taillon himself was wrapping up one of the best seasons of his career. Though his time with the Cubs had a rocky start from a performance perspective, it’s turned into a rousing success story. And between him and Shota Imanaga, the Cubs have hit on their starting pitcher signings the last couple offseasons, without outbidding teams for the top free agents.

All indications are the Cubs are approaching free agency from a similar angle this offseason. They aren’t expected to compete for top free agent starters, a group headlined by Corbin Burns, who are poised to collect contracts in the $200 million range. Two-time Cy Young winner Blake Snell was the first of that tier to go, agreeing Tuesday to sign with the Dodgers for a reported five years and $182 million.

By comparison, the four-year deal Taillon signed two years ago was worth $68 million. And last year, Imanaga signed out of Japan for a guaranteed $53 million over four years, with the option to extend the deal to five years and $80 million.

The Cubs have the market size, international draw and resources to compete on the free agent market with the movers and shakers of the industry, but they’ve been more conservative with their spending – a tone set by ownership. That said, there are still good pitchers available in the mold of Taillon or Imanaga.

Right-hander Roki Sasaki, the 23-year-old Japanese phenom who is set to move from Nippon Professional Baseball to MLB this offseason, is an extreme example of huge potential for a small financial investment. And the Cubs are expected to pursue him when he posts. But the team will also be looking domestically. So, it's worthwhile to examine what's made Taillon's signing really pay off.

When the Cubs signed Taillon, he was already a proven starter with parts of four major-league seasons with the Pirates and two with the Yankees under his belt. But they saw potential for more, leading to their early and persistent pursuit.

Taillon struggled at first, to the tune of a 6.93 ERA through his first 14 starts as a Cub. But once his mechanics and routine clicked, he proved it was a lasting change.

Even after a spring training back injury delayed his 2024 season debut, Taillon posted a 3.27 ERA in 28 starts. He said his workload (over 165 innings) and ability to compete on days when his stuff wasn’t at its best were the accomplishments he took the most pride in this season. He also settled in as a leader, which will be especially important in the wake of Cubs stalwart Kyle Hendricks’ departure in free agency.

“He's been around the game a long time,” right-hander Hayden Wesneski said of Taillon. “He's seen a lot. He's done a lot. … He understands a lot of people, from the Cody Bellingers, the MVPs, the guys who have made a lot of money playing baseball, to the guys that are just trying to make it.”

Wesneski (right forearm strain) was one of the young Cubs pitchers who was limited by injury this season. And Taillon, who has gone through everything from two Tommy John surgeries to cancer treatment, regularly checked in with Wesneski, rookies Jordan Wicks (right oblique strain) and Ben Brown (neck), and even prospect Cade Horton (subscapularis strain) as they all went through injury rehab programs at the Cubs’ Arizona facility.

If they can stay healthy, those pitchers are in line to help stabilize the rotation or contribute out of the bullpen next year. And the rotation as a whole, led by Justin Steele, Imanaga and Taillon was already a strength this past season, despite the Cubs’ disappointing 83-79 finish.

Another starter joining that front-end mix would make a Cubs rotation that posted a Top-6 ERA in baseball last year (2.77) – albeit under pitcher-friendly conditions at Wrigley Field – an even stronger anchor for the team.

“I don't know what we're going to do, or what direction we're going head, or how we're going to push us over the top,” Taillon said of the offseason. “But we've spent the whole year saying we have a really talented group, so my goal would just be to come forward and show that as a group, that it's not just something we're talking about. I truly believe we have a really special group and that we can accomplish things together as a group and bring winning baseball to Wrigley Field next year.”