Updated: 1:55 p.m. | Posted: 11:45 a.m.
The Minnesota Twins fired general manager Terry Ryan on Monday after skidding to the worst record in the American League.
The Twins entered the day 33-58, 21 games out of first place in the AL Central. Only Atlanta had a worse record in the majors.
Firing Ryan also calls into question the future of manager Paul Molitor, who was hired to replace Ron Gardenhire before the 2015 season.
Molitor helped the Twins become one of the surprise teams of season last year, having them in the playoff hunt into the final week of the season. But the Twins are on pace for 100 losses this year.
Assistant GM Rob Antony will take over on an interim basis.
Owner and CEO Jim Pohlad made the announcement hours before the Twins opened a series in Detroit.
The timing was curious, given the fact that the team had just come out of the All-Star break with the front office intact, and the trade deadline is just two weeks away.
"Terry has been a gifted leader of the baseball department for over 18 seasons," Pohlad said. "It is impossible to overstate his contribution to our game, our team and the Upper Midwest baseball community. The decision to part ways with Terry was difficult, painful and not obvious."
Ryan spent two stints as general manager of the Twins, taking over in September 1994 helping the franchise emerge from a decade worth of futility to become one of the models for small-market success in the early 2000s.
He helped build one of baseball's strongest farm systems and made several shrewd trades that turned the Twins into a team that won four AL Central championships in five seasons.
Ryan stepped down after the 2007 season but returned in November 2011 after hand-picked successor Bill Smith could not continue the team's success.
The Twins are in the middle of their fifth losing season in the last six years, and a 2015 season that saw them return to contention in the division proved not to be enough when the team sank to the bottom of the American League this summer.
Ryan handed out big money to pitchers Ervin Santana, Ricky Nolasco and Phil Hughes in an effort to address the team's biggest weakness in the starting rotation, but all have been disappointments.
The decisions to sign South Korean slugger Byung-Ho Park, hold on to veteran third baseman Trevor Plouffe this offseason and move promising youngster Miguel Sano from third base to right field all proved to be ill-fated.
Sano was injured while playing in the outfield and is back at third base, Plouffe is on the disabled list and his trade value has been diminished and Park has been sent to Triple-A to try to ease his transition from Korea to the United States.
Despite the Twins' massive struggles, the midseason firing is a highly uncharacteristic move by the Pohlad family, long known in baseball circles for loyalty and continuity. Jim Pohlad has made no secret of his admiration for Ryan, saying as late as last year that the GM could hold his post for as long as he wanted.
"While disappointed we were unable to bring Minnesota a third world championship, I leave the GM post with immense pride in being part of the Twins organization for the better part of three decades," Ryan said.
"I'm grateful for the leadership opportunities provided by the Pohlad family; the collaboration and talents of my colleagues in the front office; the hard work and dedication of our manager, coaches and clubhouse personnel; the commitment and professionalism of our players; the passion and attention to detail of our minor league staff and scouts; and most importantly, the incredible support of our fans. It's been an honor to be part of the Twins organization and I wish everyone nothing but the best going forward."
Antony is in his 29th season in the Twins organization and his ninth as an assistant GM.