After 13 years at the helm, the daily grind of the job had finally caught up with him, and he was ready to serve as a scout and senior adviser to Bill Smith, whom he recommended to be his replacement as GM.
But after just four years, Ryan is back as interim general manager, replacing Smith, and even Ryan said he never would've believed it if he would've been told he'd be back as a GM someday.
"I would've called you crazy, because if you go back and look at the tape, I said I didn't think I'd ever do this again," Ryan said at Monday's news conference alongside owner Jim Pohlad and president Dave St. Peter. "Under the circumstances, it's a different time and a different place, but I wouldn't be standing here if we were winning. I know that. It's difficult, because we let a close friend go here. I'm as close to him as anybody."
Ryan, 58, said he's ready to take on the challenge of being a general manager once again, and that he remained busy in his role as senior adviser, which also kept him up to speed on the state of the organization.
"I've been away for four years, but I didn't take much time off, frankly," Ryan said. "I was still working at a pretty good clip. If Bill wanted me to do something, I did it. But there's a need right now, and I certainly believe in continuity and stability and what we stand for in the organization."
But as Ryan made sure to note, his official title is interim general manager, as he said he's not sure if he'll be on the job for one year or 10 years.
"I would say that if I like this job, I think Jim will let me stay," Ryan said. "If I don't, I'm going to try to set up a successor."
Ryan had a similar role in helping name Smith his successor in '07, and said he feels like he should shoulder some of the blame for Smith's dismissal.
But he also praised Smith for the work he did -- the Twins won two American League Central titles (2009-10) under Smith and narrowly missed another chance at the postseason when they lost a dramatic Game 163 to the White Sox in '08 -- and said he hopes Smith remains with the organization in a new role.
"I've talked to Bill a lot the last few days," Ryan said. "I wanted to make sure he was OK. He provided a lot of the success we had here for the better part of the 2000s. I was worried for him and his family, but he's going to be OK. I'm hoping he comes back. We can find plenty for him to do, I can tell you that."
Ryan said he also plans to keep vice president of player personal Mike Radcliff and assistant GM Rob Antony as his top advisers, and that the club is also expected to name former Reds GM and Twins assistant GM Wayne Krivsky as a professional scout and assistant to the general manager later this week.
He said Radcliff, who has been with the club since 1987, might see his role might change a bit, as he's "spread too thin," and that he'll remain a valuable asset in regards to amateur scouting. Radcliff was also a candidate for the Orioles' GM position this offseason, but the Twins declined to let him be interviewed for the job that eventually went to Dan Duquette.
"I think Mike's got a lot on his plate," Ryan said. "I think one of the strengths I have is putting personnel on the roster so that will help Mike some. But we've got the No. 2 pick in the Draft this year -- it's important that we get good looks for that selection -- but I would try to take the load off a few of these guys. But for the most part, we're going to remain intact."
Antony, who just finished his 25th season with the Twins and his third as assistant GM, could also have a more prominent role moving forward, according to Ryan.
"Rob's done a wonderful job," Ryan said. "He's got a knack for those contracts. He's got a knack for baseball. He's got a lot more patience than some. And he's got a good rapport with agents, particularly with the players we have that are represented. If anything, I'm going to see if I can delegate more to Rob."
And Krivsky, who spent 12 years with the Twins before leaving to become the Reds' GM after the '05 season, is expected to serve mostly as a scout. He was fired by Cincinnati as GM in '08 before becoming a special assistant with the Orioles and Mets.
"He is going to do more professional scouting than anything," Ryan said. "But I'll obviously lean on him a lot, because I value his opinion."
All three could be candidates to take over for Ryan once he decides he's ready to step down as GM. But for now, Ryan is excited about his second go-round as Twins GM, even though he's replacing the man he originally recommended for the job.
"I didn't want Bill Smith's job," Ryan said. "But I think I can do the job for this organization. I'm anxious to get going. I'm more than happy to step in here and try to get the job done."