"I mentioned to him at the end of the year that I was likely to bring somebody in from the outside to be my principle eyes," MacPhail said. "He said to me, 'I don't feel like I'm earning my paycheck,' so that's how it came about. I'm really not surprised."
Duquette previously worked with the Mets for 14 years and with the Astros for one, and his presence helped replace former executive Jim Beattie when he signed on with Baltimore. Duquette made many of the phone calls that led to trades and free-agent signings for the Orioles and wound up with reduced autonomy once MacPhail came on board.
That adjustment was fine, but Duquette said he couldn't deal with a further marginalization. He went from having too much on his plate to looking for things to do once MacPhail arrived, and couldn't imagine how he'd help in a reduced capacity.
"A lot of the things that I did on a regular basis, Andy assumed," he said. "Understandably so -- that's what he was brought in to do. From my standpoint, what I tried to do was help give an understanding of how we were at this point and be available to anything he asked me to do. ... My new role was to not only fit in, but to assist in any way."
There was one year remaining on his contract, but Duquette thought it better to move on now and find a better work situation. He said he thinks the long-suffering Orioles are on the right track and credited MacPhail, a lifelong baseball man, for making things more comfortable than they might have been under other circumstances.
"Andy made a difficult situation easy," he said. "I've seen and observed other situations in baseball that are almost untenable. He reached out to me very early in the process and wanted to hear my opinion. That didn't necessarily have to be the case."
Duquette played a key role in several of Baltimore's recent personnel moves, including the signings of Kevin Millar and Ramon Hernandez in 2005 and the trade for Corey Patterson that same offseason. He also was largely responsible for the ill-fated trade that sent Jorge Julio and John Maine to New York in exchange for Kris Benson, who missed 2007 with a shoulder injury.
Despite the team's record on the field -- Baltimore has had a losing record for 10 straight seasons -- Duquette said that things may be on the verge of turning around. He consistently championed the organization's stock of young pitchers while he was on board, and he said Friday that the conditions may not be as dire as they appear on the surface.
"I think that there's been some good things that have happened here," he said. "I certainly feel the [team] is going in the right direction. ... With Andy coming on board, from my own perspective, my own personal duties changed."
The next decision in the front office may involve Flanagan, the executive vice president of baseball operations. The former pitcher and broadcaster has been in a position of power in the front office since 2002.
Any decision will likely be made before the Winter meetings, which will take place in December.
"Mike and I have talked about different things; we haven't decided on an imminent course," MacPhail said. "I'm hopeful that he'll stay in the organization and I suspect that is the way that it will turn out."
From Duquette's perspective, the resignation will allow him a chance to step back from the job and reconnect with his family. But make no mistake about it -- he's hoping to land a more meaningful role with another organization by next season.
"Thats certainly a goal, to be with another organization before [Opening Day]," he said. "But I do need to spend a little time away and recharge my batteries ... I'm not sure what that's going to entail as of yet, but I have some ideas. I won't have any troubles coming up with things to do."