[4] Maddon began his professional career playing in Minor League Baseball as a catcher, signing with the California Angels organization as a free agent in 1975.

[6][7] In 1979, after spending four seasons trying to make it as a catcher in the Angels organization, Maddon decided to give up his playing career and become a coach.

[8] He started as a scout and would continue on to such positions as manager in the Angels farm system and Minor League roving hitting instructor.

They had yet to have a winning season but were hopeful due to the development of young homegrown stars David Price, Evan Longoria, James Shields and B. J. Upton.

He led a team of young players that won the American League East over the heavily favored New York Yankees and Boston Red Sox.

[25] When MLB ordered in April 2010 that managers and coaches wear the official team jacket or approved Majestic pullover over their jersey, and not "hoodies", Maddon complained that "it's almost like a security blanket for me.

[11] They lost Matt Moore to Tommy John surgery and dealt with constant trade rumors regarding such stars as David Price and Ben Zobrist.

[37] On October 14, 2014, Rays' General Manager Andrew Friedman left Tampa Bay to assume the role of President of Baseball Operations for the Los Angeles Dodgers.

[11] Almost immediately after news broke of Maddon's departure from St. Petersburg, rumors started linking him to the Cubs' managerial position; which, at the time was held by Rick Renteria.

[44] The Rays filed tampering charges with MLB, claiming that the only reason Maddon opted out in Tampa Bay was due to his becoming aware that the Cubs would offer him a deal that would make him the highest paid manager in the game.

Cubs President Theo Epstein claimed that he had sent an email to MLB to be certain that Maddon was indeed a free agent before contacting him about their managerial position.

On May 14, 2015, Maddon logged his 800th managerial win in a 6–5 home victory over the New York Mets, placing him eighth among active managers.

[48] At the conclusion of the first half of the season, the Cubs held a record of 47–40, good for third place in the highly contested National League Central division.

[49] After coming out sluggishly after the All Star Break, Cole Hamels of the Philadelphia Phillies no-hit the Cubs at Wrigley Field on July 25.

[51] The Cubs continued their hot streak throughout the second half of the season, which included a no-hitter by Jake Arrieta on August 30 in Los Angeles.

They entered the postseason as heavy favorites, and dispatched the Giants in four games with an amazing four-run 9th inning comeback in the clincher at AT&T Park.

The Cubs made several free-agency acquisitions to bolster their pitching staff, including former Dodgers Yu Darvish and Brandon Morrow.

Chicago lost both the tiebreaker and the subsequent Wild Card game at home, the latter of which came against Colorado in 13 innings[68] The Cubs opted not to extend Maddon's contract during the 2018 offseason.

After the team limped to a 1–6 start through its first seven games,[71] the Cubs overtook the St. Louis Cardinals for first place on May 5 with a three-game home sweep of the division rivals.

Through the remainder of the 2019 season, the Cubs played sub-500 baseball with a 60–64 record, which included a two-month stretch where the team did not win a road series.

However, the Cubs remained in contention for both a Wild Card spot and the Central Division heading into the final 10 games of the season, seven of which were against the division-leading Cardinals.

[75] Maddon's final game as Cubs manager was a 9–0 loss to St. Louis that clinched the division and ended a four-year playoff drought for the Cardinals.

In February 2021, Maddon announced that he would allow Shohei Ohtani to both hit and pitch following his 2019 Tommy John surgery recovery and 2020 setback.

Maddon and the Angels adopted a 6-man rotation to allow Ohtani to pitch once every 7 days and serve as designated hitter in-between.

[14] A month before the start of the 2022 season, Maddon told the media that he was considering the possibility of moving veteran superstar Mike Trout out of center field to a corner outfield spot in an effort to prevent injuries.

[84] On April 15, 2022, in a game where the Angels trailed the Texas Rangers 3–2, Maddon ordered that Corey Seager be intentionally walked despite the bases being loaded, making the score 4–2.

The Rangers then went up 6–2 in the inning after a sacrifice fly hit by Mitch Garver and a balk by Angels pitcher Austin Warren that scored Marcus Semien.

It was the first instance of a manager ordering an intentional walk with the bases loaded while trailing in the game since Jim O'Rourke of the 1881 Buffalo Bisons.

[85] On June 7, 2022, as the team reached a 12-game losing streak, Maddon was fired by the Angels upon a visit to his Pasadena home by general manager Perry Minasian.

[87] Maddon's organization, Respect 90 Foundation, hosts a charity golf tournament annually in his hometown of Hazleton, Pennsylvania.