Bill Singer

I had first met Singer in the summer of 1966 after my second year of law school. I was serving then as a summer clerk at the Ross, Hardies, O’Keefe, Babcock, McDugald & Parsons law firm in Chicago. He was had already started there as a new associate lawyer recently graduated from Columbia Law School. After my law school graduation in June 1967, I passed the bar exam and joined Singer as a full- time associate attorney at the firm until I entered the Army in May 1968.

Bill Singer, Dick Simpson, Leon Despres 1973

Then in late 1968, when Bill learned I was going to be stationed at the Pentagon in Washington, he suggested I look up his wife Connie’s sister, Judy Arndt, then working on one of the Congressional staffs. I took him up on his suggestion. As fate would have it, a few years later Bill and I were briefly conjoined as brothers- in-law.


This temporary state soon ended as the two sisters divorced the two Bills and all of us headed off in different directions.

Singer Wins Aldermanic Race 1969 copy

AP wire service photo of Singer victory speech for sale for $10 as Historic Image 1969

During my time in the Army from 1968 to 1971, Bill had started a successful political career while continuing to practice law. In 1969, as I was settling into my Army work dealing with its newly created civil disturbance mission, Dick Simpson was managing Bill’s winning campaign to be elected an independent Democratic alderman of the 44th Ward in Chicago’s Lincoln Park neighborhood.

Later in the decade of the 1970s, the Regular Democratic Organization under Mayor Richard J. Daley had the ward maps redrawn in hopes of squelching Singer’s independent political movement. Bill Singer for Mayor Poster 1975Nonetheless, Singer was elected in the newly redrawn 43rd Ward and Dick Simpson became 44th Ward Alderman. Both men were constant and articulate critics of the Daley era’s centralized control over the politics of both the City and Cook County. They were up against powerful headwinds, as Daley’s wildly successful patronage- based political organization wasn’t called the “machine” for nothing.

Before I left the Army in 1971, another Ross, Hardies associate, Jared Kaplan, had called me from Chicago to say he was coming to Washington on business and would like to have lunch. I invited him to join me for a sandwich in the Pentagon’s central courtyard, then open to civilian visitors. During lunch, he told me that he, Bill Singer and some other Ross, Hardies lawyers would shortly be leaving the firm to start a new smaller law firm. He wanted me to join them.

At the time, I was turning 28 and felt that my time in the Army had put be behind my law school contemporaries in pursuing my legal career. Almost all of them had been able to pursue their legal careers without a three-year interruption for military service. At the time, I was having a hard time remembering what if anything I had actually learned in law school. I thought that though it would be riskier to turn down my standing offer to rejoin Ross, Hardies, joining a startup firm would likely give me more experience and responsibility sooner in the practice of law. My thinking was that this would also let me catch up to my peers sooner than if I were to go back to a larger, more structured law firm. With the die cast, I left the Army in spring 1971 to practice at the newly established law firm of Roan, Grossman, Singer, Mauk & Kaplan (later Roan & Grossman). Not returning to Ross, Hardies turned out to be fortuitous for me as the firm shortly thereafter was forced to lay off most younger lawyers after its largest client, Peoples Gas Company, decided to fire the firm and create its own in-house law department.

Bill Singer, while 43rd Ward Alderman and a partner at the new Roan & Grossman law firm, had successfully joined with Jesse Jackson and other liberal anti-machine forces to successfully challenge the seating of Richard J. Daley’s delegation of regular Democrats at the 1972 Democratic Convention in Miami. This success, and attendant publicity led Singer to give thought to challenging Mayor Richard J. Daley in the mayoral Democratic primary race to take place in February 1975. Singer announced his candidacy on October 15, 1973, leaving himself a full 18 months to raise funds and campaign throughout the city.

During this period, Singer asked me to become Secretary of his 43rd Ward organization, and later, as his campaign picked up steam, to join the campaign full time. Being eager to take on the challenge of what I thought was a worthy battle, I took a leave of absence from Roan & Grossman and became General Counsel and Director of Research of the Singer mayoral campaign.


As the campaign grew more frantic and Singer’s time got stretched thinner, I also began writing occasional speeches, campaign statements and press releases, as well as position papers on various issues of the day.