"I certainly see enough for two or three more years, for sure," said Gillick, now a special assistant to the Phillies. "I kind of got the feeling when I came here this year that Chooch, Rollins, Howard, and Utley, they want to win. They really want to win. When people have that attitude, it carries them a long way."
It's not shocking that only seven players remain from Gillick's last team. Tampa Bay, the team the Phillies beat in that World Series, has only four players left from the 2008 season. The asterisk among the Phillies' seven remaining players is reliever Chad Durbin, who left for two years before returning this season. (Kyle Kendrick is the other holdover.)
In the years since Gillick stepped aside and Ruben Amaro Jr. took over as general manager, the organization has had to make some difficult decisions. There's a thought that the Phillies have regressed under Amaro because they have taken a step back in each of his four seasons. That's a silly way to look at it.
All you can do in this four-tier playoff era is get in and give your team a chance. Amaro's Phillies have done that three times in his four seasons, with last year being the exception.
That's not to say that the current general manager has made all the right moves in assembling his rosters. But nobody understands better than Gillick the risky business of being a general manager.
"Sometimes it's pretty obvious the players you should let go, and what maybe isn't so obvious is the players you should retain," Gillick said. "You have to decide what players to keep as the nucleus of your club."
Gillick said that when all things are equal, talentwise, you should first keep the players who came up through your own minor-league system.
"With free agents, it's sort of like a marriage," he said. "You think you know someone and then you get married. Then you get into it and it's not what you really thought it would be."
The same can be said about trades. The Phillies had one perception of Hunter Pence when they got him and it had changed entirely by the time Amaro traded him away at last year's deadline.
Shane Victorino, the other player shipped out at the deadline, was considered a player in decline, an evaluation front-office people are always making. Given Victorino's contributions on and off the field, it wasn't an easy move for the organization, but the Phillies thought it was time, and you can be sure Gillick had input into the decision even if it was Amaro who had to sign off.
"If a player's skill level is decreasing and you can see it, that's an easy decision you make for yourself," Gillick said. "But if you have two players whose levels are very similar, I've usually had a tendency to lean toward the player who began his career in the organization."
That's the model that Amaro has mostly followed. The Phillies allowed Jayson Werth to walk, but gave huge contract extensions to Howard and Rollins. Utley received his seven-year extension while Gillick was still the general manager. Amaro has also carved his own identity by spending big money on pitching, an option that did not become available to the Phillies until they started routinely selling out Citizens Bank Park in 2009.
Difficult decisions lie ahead following the 2013 season, when the homegrown Ruiz and Utley can be free agents.
"Those decisions will be very difficult," said Gillick, who admitted he cried as the Toronto Blue Jays GM when he decided to sell Willie Upshaw to the Cleveland Indians in 1988.
"We both cried," Gillick said. "There wasn't a better person than him, but we felt we had to do it."
Gillick, 75 and a Hall of Famer, has been making those kinds of decisions for years. After the Blue Jays won their first World Series in 1992, he let Jimmy Key, David Cone, Tom Henke, David Wells, and Dave Winfield walk as free agents for various reasons.
He found the right people to replace all of them, and the Blue Jays won another World Series the following year by beating the Phillies. That's why that Toronto team is remembered as one of the best in baseball history.
This core group of Phillies still is trying to achieve that same level of success.
"It would be nice," Gillick said. "Ruben came close in '09. We lost in '10 and '11. The Giants . . . have to be considered great, and I think to be considered an elite team you have to win a couple of times over a short period."
Contact Bob Brookover at firstname.lastname@example.org. Follow @brookob on Twitter.