The Joy of Politics

I try not to dwell on the past. I resist introspection, having spent much of my early life doing way too much of that.

But I’ll make an exception this morning to recall that 20 years ago I woke up to find that I had been elected Mayor of Madison the night before. It had been one hell of a fun campaign.

My friend Jeanne Hoffman volunteered to run my campaign in the early going while I looked around for an experienced manager. Everybody I asked turned me down. Finally, less than four months before the April election I got a lead on a young woman who was in Louisiana and had just finished running field operations for a U.S. Senate race down there. She was 24 and had never managed a campaign before.

Her name was Anna Landmark and it turned out I had served on the Dane County Board years earlier with her dad, Jerry. I offered her the job over the phone, having no other options. She took it, needing a job and having no immediate options herself. A few days later I walked into my campaign office and noticed a young woman sitting quietly just inside the door. I walked right past her and into the inner office. Then I thought, ‘wait a minute.’ I walked back out and said, “You’re Anna, right? I’m your candidate. Sorry, this is what you get.”

Anna Landmark turned out to be brilliant with nerves of steel. Nothing rattled her. I’d pop into the office with some hare-brained idea and she’d just look at me with a look that said, “I’ve got this. Do as you’re told. Now if you don’t mind, I’ve got serious work to do.”

Her partner in crime was Thomas Dewer. I ran into him one morning at the Blue Plate Diner early in the campaign. I was shocked that he knew who I was. Nobody knew who I was. He volunteered on the spot. It turned out that he was a sort of man-about-town, connected to everybody and very active on social media at a time when people were just figuring out what that was and how to use it effectively. It also had a hipster vibe — your grandmother was not yet on Facebook — and Thomas was well-known in that community.

Jeanne, who ran the Wisconsin Bike Fed, also had that Madison hipster connection and between the two of them and musician/legislative aide Tom Powell, the campaign developed a personality. I was just about the most unhip guy there was, but they made me so unhip as to be hip. We had lawn signs — we had a million lawn signs — that read Dave Cieslewicz for Mayor on one side and the whole thing spelled out phonetically on the other. Not just chess LEV ich, but also dav and may-or.

Ward Lyles, who later became a professor, crunched numbers and targeted voting wards (Ward of the Wards, we called him), The unflappable Barb Irvin kept the office running and did just about everything that needed doing. Dan Kennelly kept my complicated schedule — he later became a planner. Mike Tate, who later ran the Democratic Party, organized the campus. Branden Born, who also became a prof, wrote position papers. Dane County Executive Kathleen Falk endorsed me early on, which was huge. Her son, Eric, helped Mike on campus, where we won despite winning neither student newspaper endorsement. (We didn’t get any newspaper endorsements.)

But before we even got to that point, we had taken a gut punch in August when Paul Soglin unexpectedly got in the race. He seemed larger than life, unbeatable. Other potential candidates dropped out and endorsed him. I called a meeting of my supporters to get their advice on what to do, fully expecting them to tell me to pack it in. To a person they told me to stay in the race. Most of them doubled down on my campaign. My wife Dianne, who had initially expressed horror at the idea of my candidacy, got her back up when Paul decided he could just reclaim what was rightfully his. The race was on.

In February we shocked everyone, including ourselves, by winning the primary, barely outpacing Soglin. (Some pundits had picked us to finish fourth among the four serious candidates.) And then we marched through the next six weeks against Paul, who I debated no less than 20 times, sometimes twice a day. We won the April 1, 2003 election by 1,200 votes. Paul came back eight years later and beat me by 700, so I like to think that I’m still 500 votes ahead.

I loved being mayor. If it weren’t for the good judgement of the voters, I’d still be doing that job if I could. But actually governing really is messy. Soglin, before he was running against me, once told me that the hardest part of being mayor is saying ‘no’ to your friends. I found he was right.

I ran again in 2007 and won pretty easily and then four years later got nocked off by Paul amid the Act 10 unrest, but also due in part to a rather reckless spending of political capital on my part. But running for reelection is nothing like running the first time. When you’re the incumbent you’re the target. You find that you’re responsible for every bad thing that has happened in the city, much of the region and, to some extent, the universe.

In that first race you’re young and fresh and a little bit idealistic. I found naivety to be a great advantage. You see all the possibilities and you’re a little myopic when it comes to the constraints. It didn’t take long to be confronted with the cold realities of hard choices. But on the morning of April 2, 2003 we had just pulled off an upset that felt almost like a movement. It was a generational change. We had great plans ahead.

I put on a pair of jeans and a sports jacket and went downtown to have breakfast with Anna and the rest of the staff. We pulled tables together at the tiny Marigold Kitchen, across from the campaign office, and we ate our eggs and drank our coffee and told stories and laughed. But the campaign was over. They’d all go off to do other things. Anna became an award-winning cheese maker.

You never know how you fit in in other peoples’ lives, whether you’re a central character or a bit player or forgotten altogether. But I know where those people fit in mine. I’ll never forget them.