After graduating from law school, he took a ten-week, 5,300-mile bike trip around the country in the fall of 1990. That year, he was accepted into the Army Reserves and simultaneously moved to Washington, D.C., to work in the Department of Justice, where he spent a lot of time in the International Law Division.
But in 1993, he returned to Chicago to work full-time at his father's company and also attend business school. But he found construction boring, too. "It just wasn't my passion," Gessler says.
Scott Gessler promoting his voter-registration ad campaign this fall on the mall.
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When he graduated from business school, his Army unit was mobilized and Gessler went to Bosnia, where he was deployed for around six months. Soon after his return, he decided to leave Chicago behind and head west. He'd spent time in California before, and the Pacific Northwest didn't seem to have the right vibe, he says. So he ended up in Boulder in 1997, jobless and at first staying with a cousin.
Denver seemed like a manageable city, he says, close to the mountains. And he appreciated the "social climate" of the state. "Colorado's a very open society," he explains. "People in Colorado don't ask what school you went to or what family you belong to. You can really sort of make your way in the state based on hard work and merit."
He eventually joined Hale, Hackstaff, Tymkovich and ErkenBrack as an associate in 2001. The law firm dealt with a range of issues, he says, but he'd always been interested in public service and policy, and knew that election law would be a big part of his practice. By 2004, election law had become his primary focus — and he had a particularly successful year, chairing six cases and winning all of them, he recalls. It was around that time that he started dating his now-wife, Kristi, who'd been a paralegal at the firm but left before they got involved. Gessler eventually went on to form his own firm with attorney James Hackstaff.
But working on election law as an attorney wasn't enough. "That's how you really begin to understand how election law affects people," Gessler says. "You see some of the things that work well and some of the things that drive you crazy.... An attorney pays for all the sins of his client."
Gessler wanted to tackle election challenges head-on instead of remaining tethered to issues specific to clients, so he decided to get into politics. He'd run for Boulder City Council in 2003 but lost — because he was outed as a Republican, he says, adding that he wasn't hiding his party affiliation. But that party affiliation made it impossible for him to consider a run for the Colorado Legislature from either Boulder or Denver, where he soon moved.
Secretary of state seemed like the best match.
Before he started practicing law in Colorado, Gessler admits, he had only vague notions of what the secretary of state actually does. As head of the State Department, the secretary of state is Colorado's chief election officer and thus responsible for working with county clerks across the state and administering all aspects of elections — including qualifying candidates, handling ballot issues, registering voters, overseeing campaign finance and tabulating votes. The office also handles the licensing of businesses in this state.
When he ran for the office in 2010, Gessler says, he wanted to make it easier for people to get measures on the ballot, reform campaign-finance regulation — which seemed headed toward unfair criminalization, he recalls — and proactively prevent voter fraud. He was up against Bernie Buescher, the Democratic incumbent who'd been appointed by then-governor Bill Ritter to the seat when Republican Mike Coffman had won his congressional seat and left the post. Gessler had made a lot of friends and earned supporters through his law practice, he says, and early on, his analysis of the polls made it clear to him that he would win. His only concern was that an American Constitution Party candidate might take votes away from him — running as governor on that ticket, Tom Tancredo was bringing out a lot of voters — but even with that threat, he was confident of victory.
Then on election day, at around 8 p.m., 9News called the race for Buescher. Reporters at the GOP watch party started asking Gessler for his reaction.
"We got on the phone with [9News] and yelled," he remembers. "Obviously, there were some problems with the election system that night."
And in fact, there had been problems. At 6:50 p.m., a handful of counties had been unable to connect to the statewide voter-registration system — so some counties were forced to turn to paper processing and extend voting past the 7 p.m. cutoff. In the meantime, they were not releasing results.
By 11 p.m., after more of the counties had reported their results, Gessler was confident enough to declare victory. 9News had been wrong: He won the race.
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So obviously...we've got a big election coming up," Gessler said. It was June, and he was speaking to a meeting of the Broomfield 9.12 Group, a Tea Party organization.
"There's always a lot of uptightness about it, lots of accusations hurled about," he told the crowd. "So let me tell you a little about what we're looking at, at least from my perspective, in the election. I mean, how do you, how do you know if you have a good election?
