John Lackey has seen it all before.
A century-plus between championships won't intimidate a guy who won a World Series Game 7 as an Anaheim Angels rookie. The Chicago market shouldn’t bother someone who restored his reputation and helped the Boston Red Sox win a title only two years after the fried-chicken-and-beer expose.
Lackey has a lot of connections after 14 years in the big leagues and wanted to join the same rotation as good friend Jon Lester. But beyond just the people, a sense of history helped lure him here, taking a two-year, $32 million deal when he could have scored a bigger contract somewhere else.
"The chance to win a world championship in this city [was why I chose the Cubs]," Lackey said. "At this point in my career, I'm trying to win. Winning is the biggest thing for me.
"These are my last couple years in the big leagues. To go out [with a championship] would be pretty dang cool."
There will be great expectations next week when Cubs pitchers and catchers formally report to Arizona. The last game Lackey pitched was in a St. Louis Cardinals uniform - when he served up a three-run shot to Javier Baez as the Cubs clinched the National League Division Series at Wrigley Field.
To say Lackey was thinking about his free-agency tour at that point in October would be too much of a stretch. But he did admit Lester - his best friend in the game - has been in his ear for some time.
Lester accelerated the rebuilding process for the Cubs when he signed a $155 million megadeal last offseason and helped change the culture in the clubhouse.
Now, Lester has reinforcements in the form of a 37-year-old pitcher with almost 2,500 big-league innings under his belt.
"When [Lackey] walks into a room, he commands the room," Lester said. "Not only because of his size and stature and all that stuff, but because of what he's done in this game. He's a two-time World Series champ. He's made an All-Star team (and had) some Cy Young runs.
"That immediately commands guys' attention. The big thing about Lack is you'll definitely know how he feels when he feels it. You need guys like that on your team.
"You need guys that keep their mouths shut and go about their business. And you need guys that aren't afraid to say what needs to be said at that time. And he's definitely that guy.”
[SHOP: Gear up, Cubs fans!]
Lackey helped fill a major offseason need for the Cubs, providing another reliable, battle-tested arm for manager Joe Maddon when October rolls around.
Maddon was the bench coach on the Angels team that won it all in 2002. Lackey acknowledged familiarity with Maddon, Lester and backup catcher David Ross helped entice him to take less money to sign with the Cubs.
But at the end of the day, it all comes back to the opportunity to end the longest championship drought in sports history.
"There's no bigger factor than a chance to win and do something special in this city," Lackey said. "You're seeing guys take less money to come here...and be a part of something special."
While Jason Heyward, the team's biggest offseason signing, said he hasn't really dreamed about what it would be like to win it all in Chicago, Lackey has no reservations about thinking World Series.
"One-hundred percent," he said. "That's the only reason I came."