The Accidental Senator

Michael Bennet’s brand of politics—moderate and pragmatic—is what many believe Congress needs. So why isn’t he more excited about being there?

May 2015

— Photography by Benjamin Rasmussen

In late 2008, Democratic Colorado Governor Bill Ritter received a political stick of dynamite when President-elect Obama announced his intention to appoint U.S. Senator Ken Salazar as his Secretary of the Interior. Ritter would have to replace Salazar, a respected Latino legislator and a popular figure throughout the state. Ritter was inundated with resumés from prominent Democrats, including Andrew Romanoff, outgoing speaker of the Colorado House; then Denver mayor John Hickenlooper; U.S. Representative Ed Perlmutter; and others. Ritter ultimately interviewed about 15 candidates for the post.

Bennet was considered a long shot. Then the superintendent of Denver Public Schools, he was best-known for his attempts to reform the district. He had never run for office, and his political name recognition was nil. The field to replace Salazar was so rich and contentious that when Bennet met with the governor, he immediately mentioned his anonymity. “He started by saying, ‘I’m the one person that if you don’t appoint me, nobody will be mad at you,’ ” Ritter says.

Bennet’s modesty obscures the fact that he comes from a family of strivers and achievers. His father, Doug, worked in numerous congressional offices and federal agencies before becoming president of NPR and then Wesleyan University. Bennet’s mother, Susanne, survived the Holocaust in Poland before emigrating with her parents and later studied art history. Bennet’s younger brother, James, is co-president and editor-in-chief of the Atlantic.

Like his father, Bennet had a knack for getting jobs for which, on paper, he had no obvious qualifications. After graduating from Wesleyan and then Yale Law School, he worked as a private attorney and at the Justice Department before realizing he hated being a lawyer. When his fiancée, Susan Daggett, a fellow Yale Law grad, got an offer from the Earthjustice Legal Defense Fund in Denver in 1997, the couple quickly embraced the move. Bennet arrived in Colorado jobless, but figuring he’d try something new, he reached out to Phil Anschutz, the billionaire investor, and John Hickenlooper, a fellow Wesleyan grad,* whose Wynkoop brewpub was helping revitalize LoDo. Anschutz responded. Hickenlooper didn’t.

Despite Bennet’s lack of business experience, Anschutz hired the young lawyer on the condition that Bennet take night classes to learn the basics of accounting and business. He was a quick study, and within a few years he was the managing director for Anschutz’s private equity division, working on billion-dollar megadeals such as the merger of Regal Cinemas, United Artists, and another theater chain. James Bennet, who regularly interacts with political and business masters of the universe at the Atlantic, says, “Michael’s the single most effective person I know.”

Meanwhile, Bennet and Hickenlooper had become friends. (“He never lets me forget that letter,” Hickenlooper says.) When Hickenlooper ran for mayor of Denver in 2003, Bennet got involved. He earned Hickenlooper’s trust when he stressed the importance of the city’s long-ignored budget crisis. As it became clear that Hickenlooper was going to win, Bennet suggested himself as chief of staff. A few days later, Hickenlooper ran into Anschutz at the gym and awkwardly mentioned that Bennet might join his administration. Bennet was still a couple of years from having his shares vest in the Regal deal, and he stood to make about $7 million once they did. Anschutz spelled it out for Hickenlooper: “Michael. Bennet. Will. Never. Work. For. The. City. Of. Denver.”

What Anschutz might not have realized was that Bennet, who had already made a few million dollars, was ready for another career change. (As of 2013, Bennet’s net worth was pegged at $12.1 million, according to the Center for Responsive Politics.) He left the Regal money behind, and today he explains, “There was a strong sense in our family that public service was something that was noble to do.”  

While Hickenlooper became a wildly popular mayor, Bennet shouldered the grunt work of running Denver. He burnished his dealmaker reputation thanks to policy victories such as balancing the city’s budget and negotiating a settlement between United Airlines and Frontier Airlines at Denver International Airport. He also had a knack for making people comfortable. “He could have easily come into that administration, as a guy who was the editor of the Yale Law Journal and was working for an incredibly successful private equity firm, and been the 800-pound gorilla,” says Cole Finegan, the city attorney at the time, who now helps run the politically influential Hogan Lovells law firm and serves as Bennet’s finance chairman. “I never saw him do that once—ever.”

But this unassuming nature also meant few people even knew who Bennet was. When the DPS superintendent told Hickenlooper that he planned to retire, they discussed who might take over for him.  When Hickenlooper asked the official what he thought of Michael Bennet, the superintendent was dumbfounded. “Who?”

Bennet had never even attended public school, and his oldest daughter was in the private Denver Logan School. What he did have, he later told the school board, was a legal background, helpful for negotiating contracts; a business mind that could manage budgets; and the political experience of working for the mayor, an obvious asset in running an urban school district. The board hired him over two candidates who had spent their careers in education.

After he’d run DPS for more than three years, Bennet found himself in the Governor’s Mansion, talking to Ritter about the open U.S. senator position. Ritter, a former Denver district attorney, was a moderate Democrat who naturally wanted someone smart, but also pragmatic. Bennet was both. “The real question about Michael was: Could he win an election in 2010?” Ritter says. “I thought he could.”

On January 3, 2009, Ritter held a press conference to announce his appointment of a beaming Bennet, as Daggett and their three young daughters, Caroline, Halina, and Anne, watched proudly. The family looked like a political postcard. Even today, Bennet remains a bit amazed by how quickly it all unfolded. “I had to start running in January 2009,” he says, “from a standstill.”
With the election just 22 months away, the new senator launched a blistering tour of the state. Bennet covered more than 30,000 miles as he introduced himself to towns large and small. Daggett and the girls often tagged along in the converted green school bus that served as the campaign vehicle. Caroline, Halina, and Anne, who would become campaign favorites in an excessively cute TV commercial, cadged a Sasha- and Malia-inspired promise of a dog from their father if he won the race.

But as Election Day 2010 neared, Bennet was in an increasingly difficult position. He had beaten Andrew Romanoff, one of those angered by Ritter’s decision, in the Democratic primary, but Bennet’s vote for the Affordable Care Act was becoming a liability thanks to widespread tea party protests and an energized GOP, which had nominated Weld County District Attorney Ken Buck as his opponent. Bennet refused to apologize for the vote. (When John King had asked him on CNN back in November 2009 if the vote was worth losing his seat over, the senator replied with a crisp “Yes.”)

Bennet’s team, led by Guy Cecil, built a robust ground campaign. They opened more than a dozen field offices and hired nearly 50 full-time organizers to coordinate thousands of volunteers. They gathered reams of electoral data and ran the results through voter-targeting software so they could predict which people were most likely to vote for Bennet. Those citizens would receive voting reminders by mail, followed by a personal contact from the campaign itself. In the race’s waning days, Bennet volunteers knocked on more than 650,000 doors and placed more than a million phone calls. Meanwhile, Bennet’s team and outside groups hammered Buck for his archconservative and often clumsily worded stances on women’s issues.

Although polls showed Bennet trailing Buck right up to Election Day, he squeaked out a victory by fewer than 16,000 votes out of 1.6 million cast, making it one of the closest Senate elections in Colorado in more than 50 years. While the candidates split among married women, Bennet won single women by a 59-36 margin. Pundits dubbed the Bennet campaign the model for the future. Its tactics became the prologue for one book (Sasha Issenberg’s The Victory Lab, about the science behind modern campaigns) and an epilogue for another (Adam Schrager and Rob Witwer’s The Blueprint, about the Democrats’ takeover of Colorado politics). Overnight, Bennet had gone from an unknown square-state senator to one of the hottest stories in D.C.

The accolades Bennet received didn’t prevent him from gradually descending into a profound funk. The campaign had been hard on his young family, and the dysfunction in Washington was wearing on him. Jon Davidson, who replaced Cecil as Bennet’s chief of staff in 2011, calls it the senator’s “political traumatic stress disorder.” Tom Boasberg, who has known Bennet since they were children—they both attended the tony St. Albans private school in D.C., and Boasberg would later succeed Bennet as the DPS superintendent—says it was one of the lowest points he’s seen for his old friend. Whenever the senator returned to Colorado, Boasberg says, he’d swing by a DPS school just to see what was going on. “He’d say, ‘What the hell am I doing? Why did I leave the public schools for this mess that is Washington, D.C.?’ ” Boasberg says.

Bennet regrouped by trying to recapture the role he had played in his previous jobs: an independent dealmaker. Over the next few years, he helped pass bipartisan legislation, including the Farm Bill; a breakthrough therapy bill that fast-tracks promising pharmaceuticals for the treatment of serious diseases; and protection of more than 100,000 acres around Hermosa Creek near Durango. He and his team also spent a lot of time focused on constituent service, such as dealing with problems Colorado residents were having with Veterans Administration health care or their Social Security checks. It’s not flashy, but it’s the kind of thing voters tend to remember come election time.

The party leadership began to take notice. Senator Harry Reid eventually tapped Bennet to run the DSCC for the 2014 midterms—a difficult job considering that he was defending seven Democratic seats in states Mitt Romney had won in 2012. Bennet accepted the job on the condition that he wouldn’t be required to rip Republicans in public, and Reid agreed. Bennet’s DSCC team was loaded with Colorado political operatives, including Cecil, the group’s executive director. So strong was the Colorado contingent that they nicknamed themselves the Bannock Street Project, after their old campaign office in Denver. They built an unprecedented field operation to turn out votes from young people, women, and minorities, and they raised $168 million—$50 million more than the Republicans.

It wasn’t enough. Bennet’s magic election dust had worn off. The Democrats lost nine seats, including those of Udall, North Carolina’s Kay Hagan, and Alaska’s Mark Begich. Virginia’s Mark Warner, who was thought to be so safe the DSCC wasn’t originally planning to spend very much money in his state, nearly lost as well. “We raised the money that we said we were going to raise, and we had the field operations in the swing states that we thought were going to be enough to win these elections,” Bennet says today, still sounding a little surprised. “And it still wasn’t enough to overcome the tide that was sweeping the country.”
Despite his commitment to pragmatism, the groundbreaking legislative deals Bennet aspires to have remained elusive. In 2012, Bennet participated in the “Gang of Eight” discussions on fiscal reform—an attempt to avoid tax hikes and budget sequestration—joining a bipartisan group of senators. Those discussions failed, and the sequestration eventually went forward. In Colorado, Bennet co-organized a bipartisan group of citizens and activists to create the “Colorado Compact,” an agreement intended to guide the national discussion on immigration. That work, combined with the DSCC job, steered him toward new negotiations on immigration, which included senators Chuck Schumer, D-N.Y., John McCain, R-Ariz., and Marco Rubio, R-Fla. This time his efforts were more fruitful; the bill they crafted would have provided paths to citizenship for undocumented workers, added 20,000 border patrol agents, and established an agricultural worker program. That bill passed the Senate in June 2013 with a 68-32 vote that included ayes from 14 Republicans.

Bennet promoted the immigration bill to anyone who would listen. In spring 2014, he brought it up again and again in town hall meetings on the Eastern Plains and the Western Slope. He’d tick off the benefits: It would reduce the deficit by $900 billion, shrink the federal debt by three percent over the first 10 years, and set aside $46 billion for border security. “This is a good bill,” he told crowds of farmers and ranchers. “I think it will pass the House if it comes up for a vote.” Ultimately, though, the GOP-led House refused to take it up.

Merely appearing to be bipartisan can start to seem like a cynical political ploy, but even Republicans tend to believe Bennet is earnest about cooperating with them. “I have no doubt his efforts toward compromise are sincere because I’ve known him for years, and he’s not a down-the-line liberal on every issue,” says Rob Witwer, the Colorado Republican who used to serve in the state House and co-wrote The Blueprint. And Dick Wadhams, the former chairman of the Colorado Republican Party who delights in tweaking Democrats—he dubbed Bennet the “Accidental Senator” in 2009—applauds Bennet’s diligence. “Since his actual election in 2010, you have to give Senator Bennet credit,” Wadhams says. “He has plunged himself into some of the most important debates going on in the U.S. Senate.”

In January, a few hours after his LWCF amendment failed, Bennet joined with 52 Republicans and nine Democrats to pass Keystone XL. He frames his vote as reasonable while simultaneously ripping both parties’ grandstanding. Refuting the liberal claim that the pipeline will worsen climate change, he cites a report from the State Department showing that Keystone XL wouldn’t increase carbon emissions. “It plugs into existing infrastructure!” he says, somewhat exasperated, noting that the oil is already being transported by rail. “On balance, as long as we’re importing fossil fuels, I’d rather import them from Canada than from the Persian Gulf or from Venezuela. Similarly, I think the [Republican] side has completely concocted its argument that somehow this is going to create a ton of new jobs in the United States and that it is vital to our economic interests.” The numbers back him up—only around 4,000 jobs will be created over the two-year construction period, and a mere 50 positions will be long-term.

This is when Bennet gets angry at the utter waste of time the politicking over Keystone XL became. His voice rises, and he smacks his pen on the table to accentuate his points. “The idea that this is Senate Bill Number 1, and that we’ve spent three weeks of the American people’s time on it, with everybody down there pounding their chest about this thing on both sides, I think has been an enormous distraction,” he says, with the clear implication: I’m the only sane one in Crazytown. The debate was rendered even more pointless a few weeks later, when  Obama vetoed the bill.

After lunch on the LWCF day, Bennet hosts several meetings with Colorado agricultural and environmental groups. When he emerges an hour later, a staffer hands him some paperwork, the documentation that his tenure as the chairman of the DSCC is officially over. He gleefully signs his name and raises his arms. “I’m out!”

It’s always campaign season in Washington, and now Bennet must pivot toward his 2016 re-election. It should be a fierce battle, and the early numbers—whatever dubious value they might have in early 2015—aren’t promising: A Quinnipiac poll released in February said just 32 percent of Colorado voters believe Bennet deserves to be re-elected, and 34 percent believe he doesn’t. The Colorado GOP still must find a candidate. Among the names being floated so far are U.S. Representative Mike Coffman, Arapahoe County District Attorney George Brauchler, and new state Attorney General Cynthia Coffman, but none are as obviously compelling as Sunbeam Gardner was in 2014.  

Bennet will have some sizable advantages. Presidential election years tend to benefit Democrats because voter turnout is higher. He had $2.9 million in campaign cash as of March, and through his work with the DSCC he’s built up a long list of potential benefactors. More than $100 million was spent on TV ads by the candidates and outside groups in the Udall-Gardner race, and those numbers should be matched or surpassed in 2016.

With his nascent minority influence in the Senate, Bennet is beginning to leverage cross-aisle relationships with veteran GOP senators such as Orrin Hatch and Lamar Alexander. Bennet and Alexander have co-sponsored a bill that would reduce FAFSA, the 10-page college financial aid form, to a two-question postcard. With Hatch, he’s proposed a bill that would recuse the FDA from regulating some health-focused apps and software. Streamlining government is a theme for Bennet; he’s said that whenever he meets someone who’s up for a Senate-confirmed position, he tells that person, “If I were taking one of these jobs, one of the first things I would do is put somebody in charge of getting rid of regulations that don’t work. I had a hard time persuading my own side [of these arguments]. I’m not going to have a hard time persuading the other side. I just want to make sure that in all these things we strike a balance.”

One of Bennet’s chief campaign challenges could end up being questions about whether, if re-elected, he’ll serve out the term. If a Democrat wins the White House in 2016, Bennet would be a strong nominee for Secretary of Education (which would presumably give him a chance to cut some of those unnecessary regulations). He was a finalist for the office when Obama was elected in 2008, and education remains one of his most passionate issues.

A higher office also might be calling. In January, Bennet caught an unexpected storm of buzz when the dean of D.C. gossip, Politico’s Mike Allen, wrote an analysis of Hillary Clinton’s 2016 presidential campaign, cataloging those who have already joined what’s widely expected to be an unstoppable freight train. (Then again, that train derailed in 2008.) According to Allen, the two top names being discussed for the vice president’s slot are U.S. Senator Tim Kaine of Virginia and Bennet.

It’s easy to see why Bennet would be considered: He’s only 50 years old but is also a congressional veteran. He’s a pro-business moderate. He’s from a key Western swing state. And he’s established an ability to raise an obscene amount of money.

The counterargument: Bennet isn’t a natural fit for the attack-dog role vice presidential candidates must fill. He also adores Colorado, and moving his family to D.C. wouldn’t be easy. And perhaps most important, given his perpetual frustration with Washington gridlock: Would he really want to be vice president, a job with no real constitutional power? Especially when he’d be working for the notoriously insular Clinton machine?

For now, Bennet denies interest in either national post. “No, no,” he tells me. “I’m running for re-election in the Senate. The question for me in running for this office, and deciding to run for it again, is whether it’s possible to save this democratic institution, the United States Senate. I don’t mean one person, I mean all the people here. And I hope the answer is yes, because if it’s no, I certainly wouldn’t want to do it again.”

Bennet’s cautious optimism (or upbeat skepticism) reminded me of a conversation we had last April, when I asked him how bad the partisanship and dysfunction would have to get before he just quit and moved back to Denver to be with his family. After all, he could easily get a job in academia, finance, or law, or maybe run a government agency for his old buddy Hickenlooper. He could make more money and never again have to deal with the likes of Mitch McConnell. At what point does being a U.S. senator stop being worth it?

He gave a short, soft laugh, and over his chief of staff’s good-natured protestations to not answer the question, he said, “It’s a fairly random set of circumstances that landed me here. But wherever you land, you have an obligation to try to make it better. And that’s the way I feel about this job.”

With that, he excused himself for a vote on the Senate floor. It was for the Paycheck Fairness Act, a piece of Democratic legislation meant to close the gender pay gap. The Republicans blocked it.

*Editor's Note 4/28/15: An earlier version of this story described Phil Anschutz and John Hickenlooper as fellow Wesleyan grads. In fact, Anschutz graduated from the University of Kansas. We regret the error.