PITTSBURGH (AP) — The Pirates fired manager Clint Hurdle before Sunday’s regular season finale against Cincinnati following a stunning second-half collapse that dropped Pittsburgh to the bottom of the National League Central and included a series of off-the-field issues.

Pittsburgh entered Sunday 69-92, including a 25-47 since the All-Star break.

Hurdle went 735-720 in nine seasons with Pittsburgh, helping the franchise emerge from 20 years of losing to reach the playoffs three straight years from 2013-15. The Pirates never advanced past the Division Series and are assured of a third losing season in their last four years. Hurdle had two years left on an extension he signed in 2017.

Pittsburgh general manager Neal Huntington called it “an extremely difficult decision” for the organization.

“Words cannot express how much respect and appreciation I have for Clint as a person and a leader,” Huntingon said in a statement. “He was the right person at the right time to take on the enormous challenge of leading our Major League team out of an extended losing streak and piloting us to three straight Postseason appearances. We will be forever grateful for his dedication to the Pirates organization on and off the field.”

Bench coach Tom Prince filled in for Hurdle as manager on Sunday.

Hurdle becomes the fifth departing manager. San Francisco’s Bruce Bochy and Kansas City’s Ned Yost announced their retirements, San Diego’s Andy Green was fired on Sept. 21, and the Cubs’ Joe Maddon and Chicago announced Sunday he will not return.

Oakland’s Bob Melvin, hired in June 2011, becomes the longest-tenured manager in the major leagues.

Hours before his departure, Hurdle said he had “guarded optimism” about the direction of the team despite its post All-Star break funk. Pittsburgh entered the break at 44-45 but promptly lost 24 of its next 28 games.

Off the field, pitcher Felipe Vázquez was charged with statutory sexual assault, unlawful contact with a minor and corruption of minors, all felonies, and a misdemeanor count of indecent assault of a person under 16 years old.

Reliever Keone Kela suspended for an argument with a team official and Vazquez and reliever Kyle Crick got into a fight that resulted in Crick needing season-ending surgery on his right index finger.