Inside the meeting that set the Cubs apart in their pursuit of Jameson Taillon

Right-hander Jameson Taillon and Cubs vice president of pitching Craig Breslow carved out about 30 minutes for lunch at Zero Bond in New York last month. They stayed for over two hours, and if Taillon hadn’t had other engagements that day, they might have talked for longer.

“I left that meeting feeling like this could be a really great fit,” Taillon said in his introductory Zoom press conference Monday.

The Cubs made Taillon’s four-year deal official on Monday. His contract is worth $68 million, a source confirmed two weeks ago when the parties agreed to terms. For Taillon, that in-person meeting — along with the individualized videos the Cubs sent — became a separator in his free agency decision.

“Everyone I talked to, it just felt easy,” Taillon said of the Cubs. “It felt right. I was impressed with every team, for sure. But the Cubs felt genuine in that regard, that they reached out early, they reached out often.”

The Cubs had other advantages as they pursued Taillon, who said he talked to “a lot” of teams. From his time with the Pirates, Taillon knew what it was like to pitch at Wrigley Field when the Cubs were playoff contenders. And the club assured him they were going to spend to improve.

Taillon sought input from ex-Cubs: his Yankees teammates Anthony Rizzo and Scott Efross, and former Pirates teammate Trevor Williams.

“All the feedback I got was like, ‘Dude, if you have the opportunity to play there, you really have to take it,'” Taillon said.

Early on, the Cubs sent him custom videos about the Wrigley Field experience, history of the team and the fan base. He said he loved the videos so much that he watched them every day for a couple weeks. No other teams had done that. And no other team met with Taillon in person.

Some free agent meetings are more formal. Others, like Breslow’s one-on-one lunch with Taillon last month, are free flowing. Breslow came armed with a tablet loaded with a series of slides on the pitching infrastructure’s insights, but those augmented the natural conversation.

“I was struck by his aptitude and curiosity,” Breslow said in a conversation with the Sun-Times.

They talked about changes Taillon made coming back from injury. Since his second Tommy John surgery, in 2019, Taillon’s mechanical adjustments have given him more ride on his four-seam fastball. He’s also separated his cutter and slider.

They talked about tweaks Taillon still wants to make to his delivery and pitch usage. He hopes to throw his curveball more and fine-tune the consistency of his cutter and slider.

Taillon impressed Breslow with his desire to take on a leadership role and help build the pitching staff’s camaraderie. From the other side of the field, Taillon had noticed Cubs veteran pitchers Kyle Hendricks and Marcus Stroman cheering on their teammates.

“There’s a level of detail and engagement and awareness to that,” Breslow said, “that goes beyond just saying things on their face.”

Taillon and Breslow “nerd[ed] out on pitching,”as Taillon put it. They discussed Taillon’s career path, the advantages of playing in Chicago, restaurant recommendations. They looked up at the clock, and two and a half hours had passed.

On Breslow’s way back from New York, president of baseball operations Jed Hoyer reached out to see how the meeting went. The Cubs had received so many positive reviews on Taillon’s makeup that Breslow wasn’t quite sure.

He couldn’t say whether it went so well because Taillon was as interested in the Cubs as they were in him, or because “he just seems like a great guy who’s super easy to talk to.”

About two weeks ago, Taillon’s commitment answered that question.

“I feel like I still have some untapped potential that I’m really trying to hunt down,” Taillon said Monday, “And I felt like this was a great fit to help me find that.”

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