True, but the Cubs are his seventh team in the last six years.
"I've never had the chance to get bored by a city -- I look at it that way," Jackson said.
He settled on Chicago for a second time -- Jackson pitched for the White Sox in 2010 and for 19 starts in 2011 before being dealt to the Cardinals -- after meeting with Cubs manager Dale Sveum and general manager Jed Hoyer in Newport Beach, Calif. Sveum downplayed his involvement, saying he went to the lunch to support Hoyer.
"For Edwin and his wife, there's a lot of questions sometimes on how I run things," Sveum said. "You just be yourself -- you don't do anything. You're there for support and understanding and to show them that you care a lot about them, and want to sign them to make those flights to sit down and take the time to talk to them."
Jackson was impressed by the attitude, saying he could tell the Cubs are trying to win.
"They had a confidence in the guys we have here," Jackson said. "They felt like they were a few pieces away from doing what the organization wants to do, and that's win ballgames. The acquisitions they made in the offseason, they picked up some pretty good guys to complete a pretty good team. It's a young team and you definitely have to be patient, but I've been on young teams before and been part of young teams when I was one of the young guys on the young team. You know everybody's potential."
At the same time the Cubs were courting Jackson, Theo Epstein, Cubs president of baseball operations, was meeting with then free agent Anibal Sanchez in Florida. Jackson knew about that, too.
"I felt if they came all the way out to where I was, then it really didn't matter what they had going on in the background," Jackson said. "Clearly, there was interest. I felt if they took the time to leave their families to meet with me, regardless of what was going on, there was definitely interest."
The Cubs were interested enough to give Jackson a four-year, $52 million contract, their first long-term deal with a free agent. Sanchez did just fine with the Tigers.
"Do I have pressure on me? I don't feel like I have pressure on me," Jackson said. "They brought me here for a reason. As far as I'm concerned, everybody is working on bettering themselves and that's all I'm working on doing.
"All I can do is go out and worry about what I can control," he said.
What the Cubs would like to see are 200 more innings from Jackson. Right now, it's been a positive vibe for Jackson in Cubs camp.
"I always take the positive from everything," he said. "Having some stability is definitely positive. You get around a group of guys for multiple years, it's a good feeling."
And the Cubs feel Jackson is a good guy. He's got experience, he works hard, and he's pretty easy going.
"He's one of those guys, you look at [Matt] Garza and a couple other dudes and they really don't put too much into contracts or what the expectations are," Jeff Samardzija said. "It's just go out, get your work in kind of type guys and that's definitely Edwin to the max.
"I think with all three of us being close guys and you throw in [Scott] Baker, [Scott] Feldman and [Travis] Wood, we have a nice core group of guys who definitely get along well and are comfortable discussing outings and future outings," Samardzija said. "I'm excited to have different guys to bounce things off of for sure."
Jackson has plenty of experiences to share. He's played in two World Series. He's been traded six times. He thought all was well with the Nationals and they chose to not make a qualifying offer.
"In this game, I learned a lot at a young age," Jackson said. "I've been on the move at a young age. I've been through adversity at a young age. I just worry about what I can control. I can't control where I was traded to, I can't control if they make a qualifying offer or not. At the end of the day, I just worry about what I can control."