Colorado’s secretary of state has spent his first year in office living up to his Honey Badger nickname by rampaging through the Legislature, chewing up his opponents, and creating all kinds of chaos. Is he out of control, or is he becoming a savvy—and ambitious—politician?
Gessler entered the workforce as a teenage busboy, first at a Greek restaurant in the Chicago suburbs, and later at a Polish eatery, where he worked alongside an older woman who didn’t speak English. “It was sort of a lower-middle-class ethnic-type area,” Gessler says. “Typical Chicago. Lots of good bohemian restaurants, and when I say bohemian I’m not talking about people who smoke clove cigarettes and wear berets. I’m talking about people who keep their lawn perfectly trimmed, and have a plastic wagon wheel, and pay for their houses in cash. That’s bohemian.”
This is an example of what Gessler’s younger sister Hollus calls his dry humor. He was born in 1965 near Detroit, and his family moved to the Chicago area about four years later. His dad, Paul, owned a construction business. When he was seven, his parents divorced, and his mom, Barbara, picked up odd jobs. She stressed the importance of volunteering and public service, and in high school Gessler—always a good student—tried many activities. He played chess. He swam. He played tennis. He was the editor of the newspaper and participated in Civil Air Patrol.
To Hollus, he was a role model. “He was a father figure in many ways,” she says. “When he puts his mind to something, he’s fair. I always respected that about him. Sometimes it drove me crazy when I was younger. If I was wrong, he’d point it out.” Although the Gesslers are mostly tight-lipped about their childhood, Hollus couldn’t resist telling one story: When Gessler was in high school, Chicago suffered a brutal winter, and one storm all but buried the family’s house. Gessler and some friends went up on the roof to shovel off the snow so the ceiling wouldn’t collapse. When a friend jumped off the roof into a snow bank, Gessler provided a demonstration of his can-do recklessness. He fashioned a one-story slide out of snow, and he and his friends spent the day careening into the yard. “It started as a chore,” Hollus says, “but moved into a winter wonderland.”
Gessler was industrious enough in high school to get accepted at Yale University, which he now describes almost casually as a “good school.” However, he was a white-ethnic, blue-collar Chicago kid, and New Haven, Connecticut, in 1983 was home to a preponderance of that other kind of bohemian, and it was a culture shock. Within three weeks, he’d been called a fascist. “I thought, ‘No, no, no; those are the guys in Germany. I’m just some kid from the Midwest,’ ” Gessler says. “I showed up in college and felt like I had walked into the set of a 1960s hippies movie because it was very, very liberal. Very liberal.”
Gessler went from being at the top of his class in high school, to being, well, average. During the summers, he worked as a runner on the Chicago Board Options Exchange. He interned in D.C. on the Hill and studied in Germany. Each semester, he’d return to Yale for more political science and history classes. After graduation, he moved back to Chicago and worked for his dad.
Gessler attended law school at the University of Michigan, where, he admits, “I had more fun...than I did in college.” During his first summer, he worked at a big law firm. He liked the pay but hated the work. Back at school in December 1988, he received two letters on the same day: One was in a FedEx package from an East Coast law firm that offered him a summer gig at a prorated starting salary of more than $75,000 per year. If he accepted right then, the firm would give him a $2,000 signing bonus. It was like winning the internship lottery.
The other letter arrived via fourth-class mail in a manila envelope. It was from the U.S. Attorneys’ Office in Illinois and contained a stack of mimeographed forms—a little crooked from being copied so many times. One form asked for his signature to confirm that the job was volunteer employment with no guarantees. He signed it.
His law degree in hand, Gessler headed to D.C. to work at the Department of Justice, covering everything from international affairs to terrorism and street crime. He also joined the Army as a reservist. After nearly three years, he decided the law wasn’t for him and again returned to Chicago to work for his father. The deal was simple: If he liked the construction business, he’d eventually take over. In the evenings, he worked on getting his MBA at Northwestern University’s Kellogg School of Management.
Gessler’s Army unit was mobilized in 1996 and sent to Bosnia. His unit was part of the first wave of troops sent in after the Dayton Peace Agreement, which stopped the fighting in* Bosnia and Herzegovina. It was a state on the edge of disaster and recovery, and Gessler had a front-row seat in a civil-affairs unit. “He’s not really talked about when he went to Bosnia and was actually in the middle of a war-torn state,” Hollus says. “I think it changed him.”
Like so many Colorado transplants, Gessler had visited the West a few times and fallen in love with it. When he returned from Bosnia, the idea of running his dad’s company no longer appealed to him, so he packed up his Jeep and headed toward the Rockies. He landed in Boulder—chosen because it was “a pretty town close to the mountains”—and ended up living in yet another bohemian enclave for eight years. “I did some consulting work, which is another way to say you’re unemployed,” Gessler says. He got married—and then divorced less than a year later. “The divorce was better than the marriage,” he says. “It was very amiable.”
Consulting wasn’t a permanent fit either, and Gessler returned to the law, joining Denver-based firm Hale, Hackstaff, Tymkovich, and ErkenBrack in 2001. About four years later, he and attorney James Hackstaff launched their own firm. Gessler soon became one of Colorado’s most well-known election attorneys. He fought to keep Ralph Nader’s name on the Colorado ballot in 2004. He represented Republican Bob Beauprez when he ran for governor in 2006. When conservative Mike Coffman ran for Congress, Gessler represented Wil Armstrong, another Republican who was running for the 6th Congressional District spot. (This position has long been a Republican stronghold, but recent redistricting changes that. A pro-Coffman political action committee was already running campaign ads on TV in January to save his now-vulnerable seat.) If Armstrong had been successful, Coffman might still be secretary of state. Instead, then-Governor Bill Ritter appointed Democrat Bernie Buescher to the position. Gessler, having spent years supporting candidates and tired of being tethered to clients, wanted to be his own person. He decided to step out front and challenge Buescher in the 2010 election.