Bill Daley told a City Club luncheon Thursday that he is “seriously” considering a run against Pat Quinn in a 2014 gubernatorial primary. (Quinn has already announced his intention to run for reelection.) 

This is not the first time the youngest Daley brother has tentatively lobbed his hat in the ring for elective office. His first flirtation goes back some 20 years, but he has always grabbed the hat back. Having followed Daley closely for years, and having interviewed scores of people who know him well while writing a profile of him, I think of the former Commerce Secretary and corporate executive as a careful, meticulous, private, thin-skinned man who shudders at reporters—think perhaps the Tribune’s John Kass—poking into his personal life, and particularly the breakup of his first marriage. 

But this may be his time. After all, at age 64, time is running out, and a poll taken last month shows Quinn to be the least popular of all 50 governors. Still, if Daley’s history holds some keys, he’ll run only if he believes a tough campaign would be worth it; in other words, only if he’s sure as sure can be in politics that he can win.

While Daley could face a formidable Republican in the general election, he probably handicaps Quinn as easily beatable, given the state’s $96 billion unfunded pension liability and billions more in unpaid bills.

Bill Daley’s name has been in the mix in races for governor as recently as 2010, but 2002 was the year he seemed most ready to jump in. But no go. In August 2001, after three weeks of speculation, Daley announced he would not run. Daley told me in a 2004 interview that “contrary to what a lot of people think, we are not financially wealthy people, and I needed, for personal reasons, to try to address that issue.” He added that he absolutely thought he could win, and so did his brother Rich. “It wasn’t about whether I would win or lose, or whether I shouldn’t run because I may lose; if you can’t lose than you don’t run. I thought there was a really good chance I’d win.”

Alderman Ed Burke told me back then that Daley was “enamored with the idea of being the candidate,” but ultimately he decided that if he were elected and served two terms, “where he couldn’t get back to the private sector,” he would be giving up the “dollars that somebody could earn….”

It sure looked back then the stars were aligned in his favor. Bill Clinton, Dick Durbin, Mike Madigan, and Paul Simon pledged their support. (On the August day more than 11 years ago that Daley announced he wasn’t running, Simon had invited people to a pep rally for Bill at his house.) The polling was good and the financial supporters were lined up.

Alderman Richard Mell, who was determined to put his son-in-law, Rod Blagojevich in the governor’s mansion, had threatened to “dirty up” Bill, apparently referring to his time as president of the Amalgamated Bank and the difficult separation from his first wife Loretta (whom he married in 1970) that Daley was then navigating. 

Before that, in the early 1980s, he had flirted with a run for Congress but didn’t do it. In 1996 he considered a run for the U.S. Senate when Paul Simon retired, but again pulled back. That time he cited family considerations, telling Sun-Times political columnist Steve Neal, “My family doesn’t want to move to Washington, and that meant that I would have been commuting every week…” Neal concluded. “Political ambitions are less important to Daley than his family.”

Neal seemed to lose patience with Daley. Six years later, Neal called Daley “the immortal Mr. Tease” and noted, “When there is an opening for high political office, Bill Daley likes to be in the mix…. [He] has just about perfected the art of tooting his own horn, getting himself mentioned on the long list of possible successors.”

While his brother Rich was mayor—that occupied 22 years of Bill’s life—the younger Daley understood that voters would be revolted by the family’s dynasty/machine running the entire state. “You go south of I-80,” former Tribune reporter and Richard J. Daley biographer F. Richard Ciccone told me,  “and lots of people would fear Daleys running the whole state.”

Now that Rahm sits in the mayor’s chair, that obstacle is gone, and I have little doubt that Emanuel would welcome a Governor Bill Daley—especially if the alternative remains Pat Quinn. When I interviewed then-Congressman Emanuel for the Daley profile in late 2004, he told me that he has a “great, dear friendship” with “Billy”; that they “talk constantly,” see each other in Michigan where they both have houses, and that Bill helped “to get me where I am….I will do whatever it takes to help Bill.”

Bill Daley had run Al Gore’s loosing 2000 campaign and recount. Gore told me in 2004 that Daley had been on lists of possible vice presidents and campaign chairmen. “He was the only person on both of those lists, and that’s a mark of how unique he is.” Gore added that when Daley agreed to run his campaign, “[I]…had to take him off [the VP list].”

Daley as VP? Speculation over the years has Daley ultimately coveting a place on the national ticket. As Ed Burke told me in 2004 while discussing Bill Daley’s Hamlet-like propensities, serious consideration for the VP spot would require that Daley run for office and get elected to something. Governor of Illinois, perhaps?

When Daley left his job as Commerce Secretary to run Al Gore’s campaign, his portrait was painted to hang in the company of his predecessors in the hall outside the Secretary’s office. He told me that he asked the artist to paint it “differently. It’s not a totally finished portrait… still a life in progress.”