"'Happy wife, happy life' is a true statement," he said Friday night at the opening of the Cubs Convention.
So it didn't take much convincing for Jackson to sign a four-year deal with the 101-loss Chicago Cubs. Fifty-two million dollars didn't hurt.
Jackson, who pitched for the Sox in parts of the 2010 and 2011 seasons, added that he was excited to play for the Cubs' fans, who were lining the downtown Sheraton on a cold Friday night.
"You have some of the greatest fans in baseball," Jackson said. "You see packed games when the team is losing."
Sure, in January, Cubs fans are great. And, yes, all season tourists help fill the park when the baseball is god-awful. It's a panic when the team doesn't draw three million, as it failed to do last year for the first time since 2003.
On Friday night, the Trekkie-like devotion of the Cubs Convention faithful was in full display when a small group started chanting Tony Campana's name in the ballroom. Heck, I think I saw fans carrying team president Crane Kenney on their shoulders, but that might have been a hallucination from a bad bison dog.
But come April, that all changes if the team flops like it has for the past four years. Wrigley Field isn't the happiest place to play when the teams are bad. Not after fans got a taste of the good life. Every year, I hear some new guy, like Jackson, spew excitement about joining this historic franchise and "changing the culture." And then by the dog days of summer, you can see reality set in. From the cynical media to the booing fans, Wrigley Field plays small when things go sour.
"That's fine," Jackson said. "If they get on you, try to bounce back and give them something to cheer for. It's not the end of the world. If you build a winning tradition, all those things change."
Jackson is the coolest guy in most rooms, but I'm wondering if he knows what he's in for on the North Side.
But as he said, "build" is the operative word around the Cubs right now. From the planned renovations to Wrigley Field to the new boutique hotel (Finally a boutique hotel in Wrigleyville!) across the street to the focus on revamping and restocking the farm system, the front office might as well sell branded shovels.
Cubs fans, and players, are hoping the worst of the teardown is over. It couldn't get worse than last season, right?
"Nobody wants to make excuses for last year, that's not what we're here for," pitcher Jeff Samardzija said. "Just to be a realist, we were in a different situation as a team, trading some guys, some young guys coming up. You have to look at it in a different light. I'm personally excited about it."
Asked why he was excited, Samardzija said, "I don't know. Really. It's just a feeling I have."
The Cubs Convention is the time for dreamers, where a 101-loss team can make the playoffs. Last year, I asked former broadcaster, the very real Bob Brenly, if he shared everyone's "unfettered optimism."
"I'm slightly fettered," he said with a smile.
If Brenly were around, and it's a shame he's not, he might be slightly more optimistic this time. While no one is expecting this team to battle for the division, the Cubs did attack their biggest weakness: third base.
No, actually they just re-signed Ian Stewart. They did fix the pitching staff though. Or at least at the Major League level.
After essentially praying for a kid in the stands to turn into Henry Rowengartner in a cinema-style miracle at the end of last year, Cubs president Theo Epstein was given the green light to sign pitching to make this team competitive. After failing to sign Anibal Sanchez, the Cubs inked the well-traveled Jackson to a four-year deal.
They also signed Scott Feldman ($6 million) and Scott Baker ($5.5 million) to one-year deals and Carlos Villanueva ($10 million) and Kyuji Fujikawa ($9.5 million) to two-year deals. All team-friendly deals with upside.
Matt Garza, the remnant of Jim Hendry's last big, win-for-the-present trade, said he'd pitch on the moon last year, but the excitable, mutton-chopped pitcher got $10.25 million to pitch here on earth in 2013. Samardzija got $2.64 million and change in his first year being arbitration-eligible. Both are healthy and ready to pitch after ending last season on the shelf.
It's starting to look like a big league pitching staff once again. That's a good start, right? Well, depends on how you look at it. The Cubs are strong on paper, weak in reality.
"No team ever has enough depth," Cubs general manager Jed Hoyer said. "I know it's cliché, but it's true. Once you feel you have enough pitching, you don't have enough. I don't think there's one team in baseball that feels really good about their pitching right now. If we could add more depth, we would."
Hoyer can't say what the Cubs would do with the minor league talent they're collecting if the team becomes competitive in the summer. The Cubs won't give away prospects for a rental or for a guy who doesn't fit in a fiscal sense down the road.
So how do you judge this team? By its on-base percentage? Its UZR? How about xFIP?
Hoyer hopes all of the fundamental things, like throwing strikes, fielding and taking pitches, will add up to a better product. But the playoffs are the goal and no one is foolish enough to say the Cubs will be playing meaningful games in October.
"Ultimately that is the truth," Hoyer said. "We get judged on going to the playoffs, we get judged on championships. It's hard to feel really good about a season that doesn't end in the playoffs. At the same, we're building something long-term."
The odds of Jackson being around in four years, given his history, are slim. But he's hoping his past is prologue to a Cubs revival.
"I've been on a team that lost 100 games and went to the World Series the next year, so you can't really focus on the past," he said. "The only thing you can do is look toward the future."
I guess Jackson is a perfect fit here. See you in the future, Edwin.