CHICAGO -- His first big league win came Aug. 21, 1996, at Yankee Stadium. Rookie Derek Jeter homered in the first inning for New York, but Chili Davis belted two homers and drove in four runs in the Angels' 7-1 victory, giving Joe Maddon his first "W" as a Major League manager.

On Tuesday night, Maddon picked up his 1,000th career win as the Cubs topped the Reds, 9-5.

He is the eighth active big league 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.

Is 1,000 a big deal? Baker still has the lineup card from his 1,000th win. It's a symbol of longevity in a business that doesn't always offer that opportunity.

"I say this all the time, we've been fortunate enough to be around to be able to get 1,000 wins," Bochy said. "It's always the players. Along with those thousand wins are a lot of losses that come with it."

Maddon's journey to 1,000 began well before that Yankee Stadium game. It all started at Class A Idaho Falls in 1981, when he listened to a scout who suggested he give up the idea of catching in the big leagues and consider coaching.

Maddon was 27 years old at the time. Besides managing the Idaho Falls club, he was the pitching coach, hitting coach, third-base coach and English instructor for the Venezuelan players. In 1982, he was the skipper at Salem and named Northwest League Manager of the Year, guiding the team to the league championship.

His Minor League managerial journey included a season with Class A Peoria in 1984 and two with Double-A Midland in the Texas League before he finally got the call to the big leagues in 1996 to be the Angels' bullpen coach.

Marcel Lachemann began that season as the Angels' manager, but he left and John McNamara took over. Maddon suddenly found himself the interim manager for a 22-game stretch when McNamara was sidelined with deep vein thrombosis (blood clot) in his right calf. The Angels went 8-14 under Maddon.

In 1999, the Angels had the worst record in baseball at 51-82, and manager Terry Collins resigned. Maddon was the bench coach at that time, and named interim again, leading the team to a 19-10 record.

Maddon got his own team in 2006, when he was named the Rays' manager and, after two fifth-place finishes, he guided Tampa Bay to a 97-65 record in 2008 and the World Series. The Rays lost to the Phillies that fall, including three one-run losses in Games 1, 3 and the deciding Game 5.

The time with Scioscia and the Angels influenced Maddon, who likes to say they giggled a lot. They enjoyed the game, and found ways to get the most out of their players. Maddon likes to keep the mood light with zany suit trips, pajama trips, live animal visits and lots of music.

"Joe's put his own fingerprints on it," Scioscia said of Maddon's managerial style. "I really like the themes when they go on a road trip. You have to be in a baseball season and live it every day with the pressure that's there for players with the intensity, with the travel, to understand how important a simple thing like when they do 'Miami Vice' [trips]. I think it's tremendous. Joe's put his little spin on some things, and a lot of that carried through the season."

Maddon took advantage of an opt-out clause in his contract to switch leagues and join the Cubs in 2015 and has racked up the wins each year. The Cubs won 97 games in Maddon's first season, a franchise record for most wins in a manager's first year (the old mark was 96, set by Jim Frey in 1984).

Last year, the Cubs won a Major League-best 103 games, which helped Maddon reach the milestone.

"It's a number that players allow you to have," Showalter said. "I think Joe understands that. Joe has been in all types of situations. ... Joe has always understood where he is and brings what that team needs. He's one of those guys that adjusts to the team as opposed to have the team adjust to him. That's important, and he's grasped that for a long time. Glad he's in the other league. ... Joe, you feel like he always makes things better."

Remember, none of Maddon's postseason wins count toward his career total.

"You look at a man who's had tremendous success, he's a great manager, that's a milestone for him," Bochy said. "Good for him. And I'd think he'll tell you the same, that he got his opportunity and he's thankful that he's been able to manage this game of baseball long enough to get that many wins."

One thousand wins is something 63 managers have achieved. Yost keeps it in perspective.

"It was special," he said of the milestone. "Going into managing, you always think that getting to 1,000 wins would be pretty cool. You'd have longevity. It wasn't as cool as winning the World Series.

"I've got more losses than I got wins," Yost said. "Big number on that end, too."

Did you know:

• Maddon is three-time Manager of the Year (2008, '11 American League; '15 National League)

• Maddon is one of four managers in Major League history to go to the postseason six or more times and not play in the Major Leagues (also Joe McCarthy, Earl Weaver and Jim Leyland).

• Maddon has managed teams to 90 regular-season wins seven times, including his first two seasons with the Cubs.