New Book Offers Insider’s Take on Richard M. Daley, Chicago’s Longest Serving Mayor


Richard M. Daley was first elected mayor of Chicago in 1989.

It was a time of fractious, racially polarized politics at City Hall and violence that had one newspaper dubbing the city “Beirut on the Lake.”

But despite the challenges, Daley would go on to eclipse the record of his father, the original “Boss” — Mayor Richard J. Daley — winning six consecutive terms as mayor.

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Forrest Claypool served twice as Richard M. Daley’s chief of staff and had a unique perspective on his leadership. Claypool is out now with a new book painting a behind-the-scenes portrait of Chicago’s longest serving mayor.

The book is called “The Daley Show: Inside the Transformative Reign of Chicago’s Richard M. Daley.”

In the excerpt below, Claypool describes what he called Daley’s “Airport Wars.”


In life, what one hand delivers, another sometimes takes away. Daley's airport ambitions had benefited mightily from the election of President Bill Clinton and the appointment of key Daley aides to top positions governing national airport matters. By the midterm elections in 1994, however, Clinton had badly overreached with his national health care plan and was reeling politically.

Republicans, led by Congressman Newt Gingrich and his Contract with America, swept into power. The national wave ushered in Republican control of all three branches of the Illinois government. GOP leaders wasted no time using their new influence to expand suburban power at the expense of Chicago.

At the center of their power play was O'Hare Airport. Northwest suburban residents had grown weary of escalating noise from O'Hare as the volume of commercial and freight air traffic continued to grow. The seemingly endless demand for air travel pushed O'Hare's capacity to its limits and fueled talk of expansion. But Republicans wanted any new airport to be on their turf. They also wanted in on the action at Chicago's two existing airports.

In early February 1995, within weeks of assuming control, state Republicans introduced legislation for a regional airport authority to supplant municipal oversight of Midway and O'Hare. The prize was control of lucrative aviation contracts and jobs and the three-dollar fee levied on each passenger moving through either Chicago airport. The income stream from passenger fees could underwrite bonds financing a Peotone airport.

A swaggering Sen. Aldo DeAngelis, the leading proponent of a third airport and suburban control, explained the flurry of Republican legislative activity.

"We're trying to squeeze Mayor Daley's testicles," he said.6

Feeling the pressure, Daley was in Springfield the following month, offering caps on nighttime flights to appease suburban Republican legislators. But Philip, whose own home in Wood Dale was a mere fifteen minutes from O'Hare, was feeling his oats and not interested in compromising with Daley. Philip went on a Chicago radio show and announced that it didn't matter if Daley capped flights, nixed new runways, or supported Peotone as a third regional airport. The Republicans were going to create a suburban airport authority to take over O'Hare and Midway—no matter what.

"Its time is due," he said.7

Back in Chicago, Daley's corporation counsel, Susan Sher, assembled her top lawyers in a desperate attempt to block the state's plans. It seemed a futile exercise, the challenge insurmountable. Municipalities are creations of state government. Local powers in Illinois are granted at the discretion of Springfield.

With the clock ticking, Daley summoned Sher to his office nearly every day for an update on the legal research.

"It was a very nerve-racking period," Sher told me. "We were aware of how high the stakes were, because these airports were literally the most important economic engine of the city, and our failure would result in a major political defeat for Mayor Daley."8

Finally, with Daley increasingly despondent, one of Sher's deputy corporation counsels advanced an unusual idea. Larry Rosenthal was a former federal prosecutor and US Supreme Court clerk. He argued that Chicago could use the US Constitution as a shield against the state takeover. Pursuant to the Constitution's Compact Clause, which provides for interstate compacts, in 1959 Congress gave standing permission for states to operate regional airports jointly. In the ensuing years, both Illinois and Indiana delegated power under this statute to their governmental units, including municipalities.

Rosenthal proposed that Mayor Daley create his own regional airport authority with a partner from another contiguous state. The obvious choice sat just across the Chicago border, less than forty-five minutes from downtown: Gary. This Indiana municipality operated its own tiny airport on the outskirts of town.

Once formed, the Chicago-Gary Airport Authority would legally stymie the state of Illinois. Under the Compact Clause, a two-state compact between Gary and Chicago would supersede any entity created by a single state legislature. Although Indiana's legislature was Republican, its governor, Evan Bayh, was a Democrat, obviating concerns of any partisan cross-state conspiracy to undo a deal. Bayh provided state lawyers to assist Gary.

"It was a novel idea, which at first we thought might be far-fetched, but the more we researched it, the more we believed it was a viable solution," Sher told me.9

Daley was ecstatic but knew the idea would only work if the process of securing the compact could be kept secret. If the governor or Republican legislative leaders got wind of it, they could move the airports takeover bill immediately. To prevent a leak, Daley confided in only a handful of trusted aides who were necessary to plan the maneuver.

Secrecy was so critical that it sometimes bred paranoia. When it was time to line up financing, the aviation attorney, Susan Kurland, brought Chicago's chief financial officer, Walter Knorr, into the conspiracy. Knorr's office shared a wall with the Budget Office, so Kurland insisted that Knorr meet with her in his office's adjoining private bathroom. The perplexed Knorr, a large man, squeezed into the tiny space on one side of the toilet while Kurland sat on its edge, carefully briefing Knorr on what was happening.

When everything was ready, Daley looked for an opening. Gov. Jim Edgar was scheduled to be on a trip to Israel during Passover and Easter, when the legislature would also be on break. It would be the perfect time. With Sher standing by his side, Daley placed a phone call to Gary's mayor, Tom Barnes.

Sher told me Daley's call went something like this: "We have something important to talk to you about. I'm sending my lawyer to see you—right now. She'll explain everything when she gets there." Sher headed toward the door, intent on avoiding rush-hour traffic. Before she passed the doorway, however, Daley called her back. "Wait!" Calling out to his longtime assistant, Roseanne Bonoma, Daley said, "Get me Earl

Earl Neal was among the city's legal elites and its most influential African American attorney. In his first two terms, Daley had leaned on Neal for counsel and trusted him as a city emissary. By chance, Earl was sitting in his office. Daley asked him to accompany Sher, who was white, to Gary, an overwhelmingly African American city. "She'll fill you in as you go," Daley said. Neal volunteered his car and driver.

When the duo arrived, they were greeted by Mayor Barnes and two members of his city council. Neal discovered that both councilmen were from his college fraternity, a bit of serendipity that lent itself to easy conversation. The ice broken, Neal and Sher explained the benefits of an interstate airport authority for Gary. Chicago would provide $ 1.5million a year for airport operations and improvements, doubling the Gary Airport's budget. It wasn't a hard sell.

With Gary on board, the final piece was joint approval. Gary's city council needed to pass the agreement, as did Chicago's aldermen. Both cities needed to comply with Open Meetings Act statutes requiring prior public notice, including the posting of an agenda at least forty-eight hours in advance. Gary went first, on the theory it was less likely to attract press attention; lawyers crafted the vaguest agenda possible while allowing it was for an airport agreement. Gary's meeting was scheduled for a Thursday evening. Chicago scheduled its special meeting on Saturday morning—the day before Easter and during the overlapping Passover celebration.

To throw reporters off the scent and take further advantage of the unique situation, Daley made the top agenda item a 36 percent pay raise for the mayor and aldermen. The odd timing of the special meeting appeared to make sense. Of course the cynical politicians would use the religious holidays as cover for their self-dealing! Taxpayers would be busy with their celebrations, and stories of the aldermen lining their pockets would be buried on the Saturday night news.

It worked. The press reported the special meeting's purpose as a stealthy power play for pay raises.

As word of the Gary city council meeting began to leak the Thursday night before Chicago's Saturday session, Daley's team finally dropped the pretense. The story of the interstate pact broke with Friday morning's newspapers—too late for any counteraction by the legislature or the governor, who was stranded in the Holy Land without a prayer of stopping it.

At the Saturday council meeting, Daley presided like the proverbial cat that had swallowed the canary. As one alderman after another stood to applaud the agreement while taking potshots at Philip and the Republicans, Daley stood at the podium with a sardonic smile. In a matter of weeks, he had turned the tables on the cocksure Republican leadership that had so arrogantly and blithely announced their imminent theft of Chicago's crown jewels.

The airports remained firmly in Chicago's grasp.

Republicans would soon seek revenge, targeting another prominent Chicago asset. But this was a glorious moment—and the most brilliant political coup of Daley's mayoralty.

Reprinted by permission of 3 Fields Books. Excerpted from The Daley Show: Inside the Transformative Reign of Chicago's Richard M. Daley by Forrest Claypool. Copyright 2024 Forrest Claypool. All rights reserved.

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