The Chicago Pragmatist

I wasn’t always a pragmatic.  After a short stint in a Benedictine monastery directly after high school graduation, I was told by the abbot that I needed to see something of life. Before I made a final commitment, I would have to spend the summer outside the bucolic walls of the Marmion Abbey near Aurora, Illinois.  If I had a vocation, the abbot told me, I could come back in October to begin the monastic journey. This was 1967 and he turned me out into what became known as the Summer of Love.  I may describe more of that period of my life in a later blog but for now, suffice it to say, I left those cloistered halls and never returned.

After a tumultuous 15 months, I came back to Chicago where I served in the Chicago Public School system for more than a decade. During one summer, I was an administrative associate for public relations to Dr. Edward Welling, who was chief of the CPS’s desegregation project.  In 1975, I took my first foray into politics with John Hoellen, of all people . . . the last Republican to run against the legendary Richard J. Daley.  I authored a white paper for his campaign delineating plans for the decentralization of the Chicago Board of Education which, as it turned out, served as the future educational platform for two progressive mayoral campaigns.  The research and writing was used as a basis for school reform legislation in the Illinois legislature that led to the formation of Chicago’s Local School Councils.  After that, I free-lanced as a writer and a public communications consultant primarily to clients involved with local governmental and political issues.

I have since returned to consulting to form Hollenbeck Strategies Inc., a consortium of fourteen independent associates that assist governments, corporations and individuals in managing and navigating the regulatory, legislative and political landscape. Throughout the years, my list of clients have included many Chicago Aldermen, several officials of local governments and various political parties, three Illinois Governors, two United States Congressmen and a former ambassador to the United States from Cyprus.

Today, I considered myself  a Chicagoan, a pragmatist and a Democrat…and in that order. For more than a decade, I was the Director of the City of Chicago City Council Legislative Reference Bureau. This bureau researched and drafted ordinances, resolutions and orders as well as analyzed and recommended policy at the request of all 50 Aldermen that comprise the City of Chicago City Council and their staff.


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