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Last May, William M. Daley, the mayor’s youngest brother, took a new job as the top Midwest executive of J. P. Morgan Chase & Company, and for the first time in more than two decades, he did not play an active role in the Presidential campaign. Nonetheless, Daley’s experience and reputation for political shrewdness kept him in demand, and Jim Johnson, a top John Kerry adviser, called for counsel when the Kerry camp was negotiating the format for the Presidential debates. Above all, Kerry’s people wanted three debates—three chances to show up President Bush and to introduce Kerry to voters. The Bush camp wanted as few debates as possible and would agree to three only if the Democrats acceded to certain arrangements—among them, that the first debate would focus on national security, and lights and buzzers would be used to keep Kerry to a strict time limit. But Kerry’s aides opposed the Bush demands. Enter Bill Daley, whose response was quick and sharp: “Every single thing that the Bush side wants is good for Kerry. If I were you, I would take the third debate and agree to everything and end the negotiations in five minutes.”
Excellent advice. Kerry won the first debate—the lights and buzzers helped keep him on point—and his floundering campaign reaped a desperately needed lift. “Bill makes no traditional assumptions—what’s possible, what’s not possible,” Johnson says today. He’s “willing to take risks that many people won’t imagine.”
A first-string team of politicians and campaign operatives say much the same thing about the youngest of the seven children of the late Richard J. and Eleanor “Sis” Daley. Indeed, Bill Daley’s particular brand of intelligence presents a curious case: He was never a top student (and he suffered embarrassment 30 years ago when—apparently without his knowledge—a state employee changed Daley’s answers to help him pass the insurance broker’s exam). He maneuvered the passage of the North American Free Trade Agreement (NAFTA) in the U.S. Congress and lobbied on behalf of the telecommunications giant SBC, but his supporters say that he probably never mastered the details of those operations. Still, people who have worked with him (and against him) credit Daley with remarkable savvy. “If you asked Bill the difference between Cicero and Plato, he wouldn’t know,” says the Chicago lawyer and Democratic stalwart Wayne Whalen, but he possesses a “keen intelligence” on how to plot strategy, to predict how people will behave in a given situation, to see beyond conventional wisdom.
As a result, Daley, 56, has played politics at such a high level that his career virtually tracks the roller-coaster history of the Democratic Party through the past quarter of a century. He started small—working in the Jimmy Carter campaign for President, advising Walter Mondale in 1984, then Joseph Biden in his aborted Presidential run in 1988. He became such a favorite of Bill Clinton’s that he sometimes had to decline when the President asked him to play golf or to watch a movie at the White House. Commerce Secretary Bill Daley, appointed by Clinton in 1996, had too much work to do. And he was at the center of the great Democratic disappointment of 2000, serving as the chairman of Al Gore’s race for the Presidency. Today, Daley’s friends say, he can pick up the telephone and call almost anyone, from Arizona Republican senator John McCain to the Citigroup chairman, Sandy Weill. At the peak of the election-night chaos in 2000, Daley called his friend Tom Brokaw, the NBC anchor, to trade the latest news on the Florida returns. Many of his best friends are tough-guy players in the mold of Dan Rostenkowski, once considered the most powerful man in Congress. Danny and Billy, as they call each other, share a love of golf and results; they are what Daley calls results rather than process Democrats—people who want to “get something done,” not people who go to Washington “and it’s all about the purity of the process.”
Daley is congenial—when the columnist Mike Royko wrote that Bill and Rich were “too dumb to tie their shoes,” Bill called Royko and told him that he and his brother were “wearing loafers now”—and discreet, and he has a near obsession with order and neatness. Rich might look rumpled, but Bill is always pressed, like a chief executive officer, with his fringe of gray hair coifed, his nails manicured, his shirt monogrammed, and his tie from Hermès. About five feet nine and said to be a StairMaster devotee, he is in good shape, and his eyes are a lovely blue-green. One woman who worked with him says that if they had a political function to go to, she would stay on the job to the last minute and refresh her lipstick; he would go home to shower and arrive looking every inch the power player.
But Daley is a power player with humility, with a reluctance to grandstand so appealing that even his opponents praise him. David Bonior, the former Michigan congressman who led the opposition to NAFTA in the House, recalls a Clinton White House dinner after the agreement passed. Bonior’s wife, Judy, says that she was seated between Bill Daley and a businessman who was “extremely enthusiastic about his position and his familiarity with everybody”; he was bragging that he was a “personal friend of Bill Daley’s.” Bill, whom Judy Bonior recalls as being rather quiet, said nothing; she did not have his restraint. “Maybe you should know, sir,” she said, “that this is Bill Daley.”
For all his success in politics, business, and law, friends suggest, Bill Daley may yet hold some unfulfilled ambitions. At times he has seemed driven to prove that he can make it on his own, without the head start provided by the Daley name and connections. And he may yet have a desire to run for office. When he took the job with J. P. Morgan Chase, kibitzers assumed that he was hired to give a Chicago identity to the New York–based firm, which had just acquired Chicago’s Bank One. Some see him as being paid to be a handshaker and a dispenser of dollars to local charities. But if that is all the position entails, friends say, he will soon move beyond his imposing office at 1 Bank One Plaza.
When Al Gore called Bill Daley in the summer of 2000 and asked him to run his campaign, Daley was the only person on both Gore’s lists of Vice Presidential prospects and campaign chairmen. “That’s a mark of how unique he is,” Gore says. Daley now insists that he was not a serious Vice Presidential contender, and former congressman Tony Coelho, who preceded Daley as the Gore campaign chairman, says that he himself put Daley’s name on the Vice Presidential list merely as “a sign of respect.”
For all its depth, Daley’s résumé lacks the one accomplishment—elective office—that he knows he needs to be seriously short-listed. If his job history had included, say, governor of Illinois, his name would have been added as more than a courtesy.
So in August 2001, when he considered running for governor, it appeared that he was set to fill the gap. “It may sound arrogant,” he says three years later, “but I thought I had a really good shot.” Many pros agreed—among them, former state comptroller Dawn Clark Netsch and Illinois Speaker of the House Michael Madigan.
Other Democrats worried that it might look as if the Daleys were trying to take over Illinois, with Bill running the state, Rich the city, and their brother John, a commissioner on the Cook County Board, the county. “I’m not sure the state of Illinois was ready for a Daley,” says F. Richard Ciccone, a former Chicago Tribune reporter and a biographer of Richard J. Daley. “You go south of I-80, and lots of people would think the Daleys were running the whole state, and they wouldn’t like that.” Rich Daley was said by some to be privately dissuading Bill from entering the race. Today, Bill says those stories are “180 degrees from the truth. He was very encouraging. He absolutely believed I could win.”
Alderman Richard Mell, who was backing his ambitious son-in-law, Congressman Rod Blagojevich, for governor, threatened to “dirty up” the mayor’s brother with talk of his separation from his wife of more than 30 years, reported Fran Spielman in the Chicago Sun-Times. But Bill Daley says his decision not to run was motivated simply by his need to make money. “Contrary to what a lot of people think,” Daley says, “we are not wealthy people, and I needed for personal reasons to try to address that issue.” That led him to his jobs in business, but it may not have permanently quelled the drive to run for high office—an impulse, after all, that goes way back.
Illustration: Shawn Barber