Gillick's next move is just as intriguing as his last four, each of which led to a previously stagnant team reaching the World Series or, at the very least, the league championship series.
In this case, the 73-year-old executive will be asking questions about the Cubs and their owners, the Ricketts family. Unless Ricketts is truly naïve, it will be Gillick's feelings about the potential of the organization that will determine if he becomes involved, more so than anything Ricketts can say or do.
Long ago, when Tribune Co. ran the Cubs, Gillick was sounded out about leaving the Blue Jays to jump to Chicago. He said thanks but no thanks because he wasn't convinced he would have the necessary resources and autonomy to succeed.
If Gillick doesn't leave his special adviser's role with the Phillies to join the Cubs at some point in the next few months, it will be a sign that things haven't really changed that much under Tom Ricketts and his siblings.
The timing couldn't be better for the Cubs, who better realize the chance they have.
Speaking on a conference call with reporters this week, Gillick was asked about his future and speculated he "would certainly consider (taking a job) if it was the right situation. …''
A spokesman for Ricketts denied a WSCR report that Ricketts recently had talked to Gillick, but he didn't say Ricketts wouldn't talk to Gillick. He would be foolish if he did anything without seeing if Gillick is ready to leave Philadelphia and take on baseball's ultimate challenge.
When Gillick was voted into the Hall of Fame last December, I wrote that the Cubs intrigue him and he would be the perfect guy to run the baseball side of the organization. The only thing that has changed since then is the need for an overhaul with the precipitous unraveling of the team under first-year manager Mike Quade.
Gillick is the right guy for the Cubs, and everybody Ricketts talks to tells him — even general manager Jim Hendry probably would, if Ricketts engaged him in such an awkward conversation. Gillick's the guy you would fire your own mother to hire if you had a chance to get him.
But what does he think about the Cubs? That's the big question.
It's funny that Gillick used the phrase "the right situation'' the other day. That's the one that always comes up when he talks about his future.
Here's what he's saying when he uses that expression.
He wants to know that he will have authority without interference from ownership. He wants to know he will have money to spend — he has spent everywhere he has been, but it's often the moves for supporting players like Jamie Moyer, Mark McLemore and Tom Henke that have made the difference — and control of his staff.
If the Cubs are going to entertain adding Gillick seriously, they have to do it before other decisions have been made, in particular Hendry's fate and the naming of his successor. He's not coming if Chairman Ricketts and President Crane Kenney make those calls, then offer Gillick a job to tutor their choice. That would not be "the right situation.''
Maybe the Cubs never would be "the right situation'' for Gillick. If that's the case, then they move on without him. But with apologies to everyone else, he's too experienced, too enthusiastic, too wise not to pursue.
Gillick would bring some of his own guys if he came to the Cubs. He always does. But he works very well with other people, so scouting director Tim Wilken (with whom Gillick worked alongside in Toronto) hardly would be the only holdover he would value.
The ideal situation would be for Gillick to blend his trusted assistants, including Gordon Lakey and Charlie Kerfeld, with the Cubs' current assets, guys like scout Gary Hughes and special advisor Greg Maddux. He might go outside to hire a GM, with White Sox assistant Rick Hahn expected to be on the short list.
One thing to keep in mind. Gillick was part of the process that led the Phillies to hiring Ryne Sandberg for their Triple-A manager's job. He might reverse the process that left Quade in charge and Sandberg in Allentown, Pa.
Only Gillick knows if the Cubs can be "the right situation'' for him. But Ricketts should be doing everything in his power to put out the welcome mat.
progers@tribune.com
Twitter @ChiTribRogers