To their chagrin, Gillick has told the Phils he's not coming back in 2009, and he's holding fast to that stance.
Instead, Gillick, 71, said he's moving back to Seattle, one of his previous general manager spots, because his wife is living there and the distance has become too great. Of course, the Mariners GM job is open again, and speculation is a daily diet in Major League Baseball circles.
The Mariners -- who finished last this season for the third time in four years -- are in seeming disarray, and have been since Gillick left after the 2003 season.
It's become a pattern in Gillick's tremendous career. He's gone to a place -- Toronto, Baltimore, Seattle and now Philadelphia -- and brought success. And when he leaves, the sunshine of that success seems to leave with him.
Gillick, though, declined to feed all the speculation. But he didn't deny that a return to the Mariners was a possibility.
"I'm comfortable with what I'm doing, and I really haven't decided what the future will bring at this time," he said, choosing his words very carefully. "Yeah, this is the fourth time I've retired, but some of them were sort of forced retirements. I'm not thinking about [the future] right now. I'm just thinking about the game ahead, the series ahead. That's my focus right now. But you never know what will happen."
Gillick left the Blue Jays in 1994 after 18 years and two World Series titles. Toronto hasn't been to the playoffs since. He resurfaced with the Orioles in 1996 and stayed there three years, through two losses in the American League Championship Series, leaving in 1998. Baltimore hasn't been close to the playoffs since.
He joined the Mariners for four years in 2000 and presided over teams that lost to the Yankees in the 2000 and 2001 ALCS. His family was in Toronto at the time, and when he left in 2003, it was supposedly for good as a full-time general manager.
But in 2005, Gillick had to scratch the itch one more time, and he replaced Ed Wade as GM of the Phillies to take them the next step into the postseason, which Philadelphia has done now in consecutive years for the first time since 1980-81.
The key to this season is Gillick acquiring a battered, but evidently undamaged Brad Lidge from the Astros last offseason. Lidge is 43-for-43 in save attempts through the first round of the postseason, an element the Phillies just didn't have on their 2007 team.
"It started off in Spring Training that we were going to win on offense," Gillick said. "Our pitching, though, especially our bullpen, turned out to be a lot better than we had anticipated. It's really our bullpen that got us here. Lidge had a tough go-around in Houston, but he's been fine for us."
During all these years of transition, Gillick and his wife moved from Toronto to Seattle, a subtle footnote to this entire litany. It is the reason he said he's leaving this job, finished or not, at the end of the month.
The Phils haven't won the World Series since 1980. They're in the final four, but there's no telling what will happen.
"I live way out in Seattle, and I haven't been home a lot in the last 10 years," Gillick said. "I've been out there working, and it gets kind of old being out there on the road. I don't get home that much. It's difficult. I'm married. My wife is out there. She doesn't get back here that much."
Gillick is not the kind of guy who will put together a "Bucket List" of all the things he wants to do before he "kicks the bucket," though he's talked about earning his pilot's license for years.
Considering his track record, Gillick was asked if high on that mythical list might be running baseball operations for another team.
"I wouldn't say that," he said. "I don't think I'll be back in this type of job again. Philly is a great place to work. Good ownership. Good people. Terrific support. You couldn't pick a better place to work."