The Big Shoulders

I've been babysitting my friend Gino's blog while he recuperates from surgery. In one of our conversations prior to his surgery, we talked about Chicago. Gino grew up in California but was born in Chicago and his family has basically shuttled between Chicago and the old country (Italy). As it happens, I was born in Chicago, too, but my family moved to Wisconsin when I was a baby. Given the excellent possibility that a Chicagoan may soon be Leader of the Free World, it seems like a good time to talk about The City of the Big Shoulders. It's feeling like this may be a series of posts -- fair warning.

Chicago is a lot of things, but most of all it's a magnet. It attracts people. The talented, the dreamers, the reprobates -- they all come to Chicago. They come to perform in its venues, work in its offices, drink in its saloons. It's a place of dazzling architecture, amazing physical beauty and unspeakable cruelty. But mostly it's a place where normal people live and work and endure. And what they endure a lot of is corrupt government.

And one of the things that is most interesting about the saga of Barack Obama is that he was attracted to Chicago. As it happens, Obama and I moved to Chicago about the same time, for very different reasons. I was just looking for a job where I could write. Never did find one, exactly, but I did end up working for a large corporate law firm in Chicago. Since I wasn't a lawyer, I ended up doing mostly administrative work and never wrote much more than memoranda.

The intersection of law and politics is a strong one no matter you go, but it's especially important in Chicago. The largest law firms were completely wired into City Hall and people with political connections were highly valued, especially as rainmakers. The firm I worked at hired a longtime Chicago politician and judge, Seymour Simon, mostly to have his name on the letterhead. We also had a one-time federal prosecutor named Joseph Hartzler, who eventually returned to the Justice Department and served as lead prosecutor in the Timothy McVeigh trial. The big law firms in Chicago have always had talented, powerful people. And without question, there was more than a little glamor there, even for those of us who were simply hired help.

Barack Obama spent time in this environment, too -- he served as a summer associate for one of the largest firms in Chicago, Sidley & Austin. He met his wife Michelle there. He met Bernardine Dohrn there as well, but that's another post. He could have pursued a safe corporate litigation career and lived a comfortable life in some fashionable Chicago enclave. Instead, he pursued a political career and now may be moving to the most famous address in the world.

What always struck me about working there was that, more than anything else, it was a very mercernary business. Our attorneys worked on huge, complicated transactions -- I recall working for several days at a closing for the sale of a large regional shopping mall, notarizing documents and helping to assemble closing books that looked like unabridged dictionaries. Often attorneys represented the other side of the transaction would be there as well and there would be an elaborate minuet going on, with cellphones and faxes. One New York firm that often came would outfit all of their attorneys in blue shirts -- it was apparently some sort of trademark thing. The sums that our firm would charge were amazing -- I would be working on a project until 10 or 11 at night and they would pay for a cab to take me home (the El was pretty dicey after about 9 p.m. in those days) and charge it to the client. What I also sensed is that a lot of the work I had to do was strictly because of the need to comply with strange regulations. This was especially true of transactions involving properties in Chicago itself. No one seemed to sweat the costs much, but I knew that the costs involved were enormous because I sometimes saw the bills.

One of the reasons that I ultimately left Chicago is that it always felt needlessly complicated. It became clear that much of the complication came from not only the regulations, but the arbitrary ways they were enforced. There are many reasons why having a Chicago politician in the White House concern me, but this sense of complication is one of the strongest. I don't sense that a lot of voters really understand what they might be voting for. I worry that the reality is going to be pretty complicated indeed. More on this in the coming days.