Michael Daley
Michael Daley, left, with his brother, Bill, in 2002
As Rich Daley counts down his last days as mayor—awash in news coverage, mostly nostalgic—I thought it would be interesting to take a look at his brother, Michael, about whom surprisingly little has been written.

While working on a profile of Bill Daley in 2004, I was told repeatedly that Michael was the most intelligent of the four Daley boys. The late political consultant Phil Krone called him “the smartest of all the brothers.” A well-known journalist called him “the brains of the operation.” The City Club of Chicago’s Jay Doherty called him “the most fascinating of all the Daleys.”

He is also the most private of the bunch. I wasn’t surprised that Michael didn’t answer my request for an interview—then or now.

Michael, 68, is the second son—after Rich. Three sisters, Patricia, Mary Carol, and Eleanor, preceded them. (All the girls became teachers; none were in politics or in public life.)

The journalist quoted above told me that Michael’s law practice could be characterized as “honest graft"—the ability and the contacts to give a matter an extra little insider push. Michael is a partner at the hyper-connected law firm, Daley and George, which was founded by the patriarch, the late Mayor Richard M. Daley. Both Bill and Richard J. were associated with the firm. John Daley, a Cook County commissioner, is the only brother who is not a lawyer.

Michael received his law degree in 1968 from DePaul and became a partner at the family firm in 1970. In 1997, a couple of Chicago Tribune reporters aptly described the firm’s style as “quiet clout.” While Michael has not broken any laws, pesky journalists such as John Kass have regularly accused him of pushing up hard against the margins of appropriate behavior—making bushels of money off of developers who do business in the city and the county, handling tax appeals and zoning and land-use cases, and collecting big fees from major banks to consult on bond business and other municipal matters. (Among Daley and George’s most notorious clients was Tony Rezko, who hired the firm to get a zoning change for a proposed townhouse development.)

Whatever the ethics of Michael’s practice, he has many admirers. The City Club’s Doherty told me: “Michael is the boss, appears to the be leader of the family. People who knew the father say that Michael is most like Richard J. He’s a great lawyer, …very modest, self-effacing type. Sometimes his hallmark contribution is letting the glory go to others.”

I was reminded again today just much privacy matters to Michael Daley. I called and emailed a few prominent locals who are close to him—former Cook County Assessor James Houlihan, attorney and Daley confidante Terry Newman, and Richard J’s deputy mayor and corporation counsel Raymond Simon. At post time, none of them had returned my call.

How his life as a lawyer will change when neither his dad nor brother presides on the fifth floor of City Hall will be worth watching. Then again, he still has a brother on the Cook County Board, not to mention another sib who works in the West Wing and is close with the president as well as Mayor-elect Rahm Emanuel.


Photograph: Chicago Tribune