The Cubs' skipper is the eighth active manager to reach 1,000 wins, joining the Giants' Bruce Bochy, the Nationals' Dusty Baker, the Angels' Mike Scioscia, the Orioles' Buck Showalter, the Indians' Terry Francona, the Pirates' Clint Hurdle and the Royals' Ned Yost.
Maddon paid his dues in the Minor Leagues, and tried new concepts, including using a 25-pound laptop computer which everyone made fun of back in what he called "the Dark Ages." He now does his lineups and research on an iPad.
"I've been part of a lot of adjustments, new concepts, new items in the game," he said.
He credited a long list of coaches with helping him reach the milestone, and, of course, the players.
"To the players who have been a part of this, I want to say, 'Thank you,'" he said. "You don't do it without the players."
The Cubs players toasted Maddon after Tuesday's game. Pitcher John Lackey, who got the win, was with Maddon when he was a bench coach on the Angels.
"He always had a great mind for the game, was easy to talk to," Lackey said. "You could tell he was going to be a manager someday, for sure."
What's been the constant over the years?
"The consistent part is simplicity," Maddon said. "Simplicity in general, but simple game plans. We're not very confusing. Players didn't go out there with a lot of thoughts in their heads. We did utilize new wave information and still do."
To celebrate the feat, Maddon's Respect 90 Foundation will donate 1,000 meals in Chicago and 1,000 in Tampa Bay.
"It's well deserved," Chicago's Kyle Schwarber said of 1,000 wins. "He's a great manager, a great one to play for. We know we have his back, and he'll have ours."
Carrie Muskat has covered the Cubs since 1987, and for MLB.com since 2001. She writes a blog, Muskat Ramblings. You can follow her on Twitter @CarrieMuskat and listen to her podcast. This story was not subject to the approval of Major League Baseball or its clubs.