Since his appointment to the Senate, Bennet has run in two elections, in 2010 and 2016, but he was so turned off by what he found in the Senate when he arrived that he almost didn’t even try to stick around.
Read: Michael Bennet wins his first race
He did persevere, and he has earned fans in government and the political intelligentsia. Few people take the job as senator as seriously, they’ll say, and no one in Congress puts the kind of premium on educational policy that he, as a former head of a school system, does.
Compare him to Kirsten Gillibrand, also appointed in 2009 to a Senate seat Obama freed up by making a Cabinet pick. She was a House member who’d flipped a Republican seat, strategically maneuvered to get her Senate appointment, and then hustled there and in the media to turn herself into an obvious 2020 candidate. She announced her exploratory committee in the middle of January on the set with Stephen Colbert, and took off on a tour of the first caucus state. Bennet started pondering a run at the end of last year, and the pondering went on for two months before he rather quietly arrived in Iowa for two and a half days of small events.
The 2020 Democratic race so far doesn’t seem like a prime breakthrough opportunity for a white man who is more comfortable having a discussion of how “the priorities of Washington have decoupled from people’s lives” than riling up a rally.
“I’m not defensive of where I am on the ideological spectrum—I don’t think that language is the language of regular people in Colorado,” Bennet says.
He is asking a lot of questions as he thinks about actually running: How late is too late to get going? How much of a campaign is realistic for someone who doesn’t start out with much charisma or much cash? Do voters actually want to have grounded conversations about the future, especially in the wake of Donald Trump?
Each time Bennet has wondered if there’s still space for him, he and his team have decided that they should explore a little more, plan some more stops, and see if there’s enough cash to be tapped out of his donor network to make this possible. There’s been a lot of talk about platforms and platitudes, they think, but not about the big issues that could make him a counterweight to Trump.
“Part of it is that I haven’t spent my whole life thinking about running for president. I’m surprised enough to be in the Senate. I’m surprised to have been in the Senate for a decade. But I have really strong feelings about where we are, and where we went wrong over the last 10 years,” Bennet tells me.
Then there is the awkwardness that another Coloradan is already running—and not just any Coloradan, but former Governor John Hickenlooper. When Hickenlooper was the mayor of Denver, Bennet was his chief of staff. It was Hickenlooper who put him in charge of the Denver schools. And Hickenlooper was also considered for the 2009 Senate appointment (some national Democrats are now urging him to run for the other Colorado Senate seat instead of pursuing his long-shot bid for the presidency).