For MLB players, their first foray into free agency can be a stressful experience.

Jameson Taillon and his agents started out in simple fashion, with the veteran pitcher making a list of teams he would absolutely want to play for.

“Obviously the Cubs were on the list,” Taillon said on the latest episode of the Cubs Weekly Podcast.

Taillon began his career with the Pittsburgh Pirates, spending 4 years pitching against the Cubs and visiting Wrigley Field several times a season. So he had a pretty good idea of what it means to be a Cub.

“Being a visiting player at Wrigley, it’s always packed,” Taillon said. “It’s a great city; I love day games. Traveling in the NL Central is the easiest of all the divisions. It just checked so many boxes.”

Taillon also leaned on his former teammates for an inside perspective on playing in Chicago and as a part of the Cubs organization.

He spent the 2021-22 seasons with the Yankees, where Anthony Rizzo was traded in July 2021 and re-signed for the ’22 season.

In July of the 2022 campaign, the Cubs traded with the Yankees again, sending reliever Scott Effross to New York.

“I did research and talked to a guy like Rizzo,” Taillon said. “He said he was at a wedding last offseason and [David Ross] was there and there were a bunch of guys there. I bumped into Rizzo in New York in the offseason and he was just like, ‘they really want you. Here’s why you’re gonna love playing there.’

“I also got to know Scott Effross really well, who was here more recently and he has a great relationship with a lot of the guys here still. So I used him as a crutch a lot.”

As Rizzo said, the Cubs’ interest was real and it was strong. The organization was looking for another reliable, stable starter for the rotation and targeted Taillon at the start of free agency.

Taillon felt that, as well. He came away impressed from conversations with Cubs front office members and it meant a lot to him that pitching coach Tommy Hottovy made a personalized recruiting video.

“I was like, this feels like a place that could be home,” Taillon said. “And then after that, it kinda just came down to contract negotiations. I felt super comfortable from the start.

“They were honest and open the whole time and made every effort to come meet with me and talk to me and answer questions.”

That all culminated in a 4-year, $68 million deal that will keep Taillon in the Cubs rotation through the 2026 season.

He entered his first year in Chicago with a 3.84 career ERA but struggled out of the gates with a 6.93 ERA in his first 14 starts.

However, from July 7 on, Taillon put up a 6-4 record with a 3.38 ERA and 1.10 WHIP. The Cubs went 10-6 in those 16 outings, which included his first career save in a rare 4-inning relief appearance on the penultimate day of the season (Sept. 30 in Milwaukee).

Check out the full conversation with Taillon on the latest Cubs Weekly Podcast: