The can-do senator in a can’t-do Congress

“You can see this corruption in the difficult decisions we avoid,” said Bennet, a principal sponsor of the amendment, his voice rising as he paced behind his desk. “It’s the tough vote we don’t take, the bill we can’t pass even in the face of urgent need.It’s the deal that can’t be reached. It’s the speech that is never made.”

For Bennet, the speech represented the culmination of nearly six years of frustration with a Congress that had become a black hole of time, energy and talent, a failing institution deserving of its 14 percent approval rating. An unlikely appointment to fill a Senate vacancy, Bennet had returned to the Washington of his childhood with an ambition to get things done and leave his mark, much as he had done back in Denver, first as a private equity investor, then as chief of staff to the mayor and most prominently as the reformist superintendent of schools. In each job, Bennet had succeeded despite what was initially a glaring lack of knowledge and experience. Now, as a first-time politician, he was trying to do it again in a Senate that seemed to defy success.

In another era, such an indictment of modern American politics by one of the Senate’s rising stars might have attracted some notice. But on this day, it was delivered to an empty chamber. Democratic leaders had taken up the constitutional amendment knowing that it could never muster the votes to overcome a filibuster. Their only purpose was to force Republicans to cast votes that might be used against them in the upcoming election. As is often the case these days, the Senate’s deliberation was nothing but a political charade, and nobody understood that better than Bennet.

Having delivered his impassioned critique of America’s political system, however, Bennet then succumbed to it. Leaving the Senate chamber, he walked across the Capitol grounds to a nearby townhouse that serves as headquarters to the Democratic Senatorial Campaign Committee, where he was serving as chairman, and spent hours on the phone soliciting contributions of up to $65,000 per household.

“It’s unfortunate, but the only way forward for those of us who want to bring in a new system is to compete and win in the old, corrupt one,” he explained. Anything else, he said, would amount to “unilateral disarmament.”

Such is the absurdity — some would call it hypocrisy — of life in the U.S. Congress, where the famous and powerful are caught in a political dystopia largely of their own making — one they all hate but refuse to change and yet are strangely determined not to leave.

For the moment, that includes Bennet. His reelection race this year is widely considered the toughest of any Senate Democrat, with more than a dozen Republicans originally vying to take him on (it’s now down to five). Outside groups have vowed to spend tens of millions to defeat him, targeting his support for President Obama on health-care reform, the Iran nuclear treaty, climate change and the closing of the prison in Guantanamo Bay. As a pro-Obama Democrat in a Republican-leaning swing state, his best hope for another term may be that he seems to defy many of the stereotypes voters have of Washington’s political class.

In an era of ideological polarization and hyper-partisanship, he is a pragmatic centrist whose instincts run to bipartisan compromise.

In the shouting match that American politics has become, he’d rather listen than talk, steering clear of the national media.

In a capital seething in self-importance, his is the rare ego that does not precede him into the room.

And at a time when politicians get ahead by being nasty, superficial and glib, Bennet gets by, as one Republican staffer put it, by being “the most affable and knowledgeable guy in the room.”

Bennet is the anti-Trump, the anti-Cruz — but also the anti-Hillary, straightforward and authentic. In many ways, he is a throwback to a bygone era, an optimist with impeccable establishment credentials who finds himself miscast for today’s politics of anti-establishment anger and resentment. Whether he is able to survive the vitriol of this year’s election and find a constructive role to play in Washington offers a test of whether there is still a place in American politics for talented, experienced leaders more interested in governing than winning.

“What people want is principled bipartisanship, and what they are getting is unprincipled partisanship,” Bennet told me. “There would be no point in running again if I didn’t believe that could change.”

Although he was dubbed an "accidental senator" when he was appointed by Colorado Gov. Bill Ritter early in 2009, it might more accurately be said that Bennet was born to the role.

The Bennets, whose ancestors arrived on the Mayflower, have been a part of Washington’s Democratic establishment since the Roosevelt administration. Michael’s father, Doug, served as a top staffer to Sens. Humphrey, Eagleton and Muskie, ran unsuccessfully for a House seat in Connecticut, held top State Department jobs under Presidents Carter and Clinton and served as president of National Public Radio.

On his mother’s side, his pedigree couldn’t be more different. Susanne Klejman was born into Warsaw’s Jewish ghetto and, with her parents, survived the Nazi genocide through the help of friendly neighbors and Catholic nuns who hid them for years. They eventually immigrated to New York City in 1950. Susanne became a librarian at Beauvoir, one of the private, upper-crust Cathedral schools where the two Bennet boys were educated, just up the street from their house in the Cleveland Park section of Northwest Washington.

Young Michael was noteworthy neither as an athlete nor a scholar — he still recalls the embarrassment of having been held back in second grade because of dyslexia he’d done his best to hide. It was only at Connecticut’s Wesleyan University, where his father and grandfather had gone, that Bennet began to show signs of the determined overachiever he would become. Upon graduation, he accepted an offer from Richard Celeste, the Democratic governor of Ohio and a family friend, to be his personal assistant. By the time he left for Yale Law School two years later, it was clear to Celeste that his young protege had “already caught the political bug.”

At Yale, Bennet was the student who got good grades but somehow made it look easy. Although Bennet would appear on campus looking like a disheveled scarecrow in his ratty chinos and Chuck Taylor sneakers, his classmates saw enough polish to his intellect and leadership potential to select him as editor of the law review. Even then, recalled Daniel Halberstam, a classmate who remains a close friend, “there was a quiet determination about him and a clear sense of purpose in life.”

From Yale, Bennet set out on a well-trod path to public service: clerk to federal appeals court judge, associate to Washington super-lawyer Lloyd Cutler, counsel to the deputy attorney general and special assistant to the U.S. attorney in Connecticut. But he found much of the legal work tedious and uninspiring — “just like another year of law review,” he said — and was uncomfortable with the adversarial nature of the legal process. When his fiancee, Susan Daggett, another Yale law graduate, was offered a job with the Sierra Club’s legal team in Denver, he abandoned the professional fast track for which he had been groomed and headed west in search of a new life and new career.

"I hear you don't want to be a lawyer anymore." The voice on the telephone was that of billionaire Phil Anschutz, whose investments in oil, railroads, real estate and telecommunications had made him one of the richest men in Colorado.

Working his Wesleyan connections — his father by now had left Washington to become president of the university — Bennet had written two letters he hoped might open doors in Denver. One was to John Hickenlooper, an alumnus who had made a name for himself as a brewpub entrepreneur. The other was a Wesleyan trustee and friend of Anschutz’s. Hickenlooper never responded. Anschutz invited Bennet in for a talk and was struck both by his intelligence and by the fact that he didn’t know a lick about business or finance. Anschutz offered him a job anyway, but only on the condition that he spend his first six months reading analyst reports and taking night classes in accounting.

“My first impression of Michael was that he needed to get his shirt ironed,” recalls Steve Kaplan of Oaktree Capital, which partnered with Anschutz on the first deal Bennet was involved with. “The second was that he was inexperienced but very smart. He picked things up extraordinarily quickly.”

Bennet went on to play a lead role as the Anschutz team quietly bought up the debt of two struggling theater chains, United Artists and Regal Cinemas, then used the bankruptcy process to gain ownership and control. Eventually the two firms were combined into an industry powerhouse, earning a big payday for Anschutz and his young managing partner.

According to Steve Cohen, another Anschutz partner, Bennet proved to be a shrewd trader and a natural negotiator. Instead of the threats and bluster all too common in finance, he listened patiently to those on the opposite side of the table, figured out what they wanted most and found creative ways for them to get it. He never pushed for the last nickel, preferring to build trust and relationships that could be leveraged in future deals. Decades later, those same skills would be cited to me by staff and colleagues in the Senate.

Bennet loved the work and appreciated the rewards: After six years, he had built a nest egg of nearly $12 million. But he was also becoming restless. At a neighborhood barbecue, he finally ran into Hickenlooper, the other Wesleyan alumnus, who by then was about to launch what was viewed as a quixotic campaign for mayor of Denver. Bennet signed on as a member of the candidate’s kitchen cabinet and threw himself into the campaign, using his newly acquired financial skills to uncover a big hole in the city’s budget. Hickenlooper won handily and was pleasantly surprised when Bennet volunteered to leave Anschutz — and $7 million in unvested stock options — to become the new mayor’s chief of staff.

Bennet became Hickenlooper’s top strategist, talent scout and chief operating officer, charged with implementing the mayor’s endless stream of unorthodox ideas. He negotiated a new contract with city workers, the outlines of a new regional transit system and a controversial settlement with the family of a police-shooting victim. What Bennet is most proud of, however, is that he cut 10 percent out of the city budget without laying off a single worker.

“Michael Bennet made me a success,” said Hickenlooper, now Colorado’s popular two-term governor. “I give him credit for two-thirds of the success we had — and yet he did it in a way that his fingerprints weren’t there.”

So when Denver’s school superintendent came to tell the mayor that he was going to leave for another job in 2004, Hickenlooper asked him what he thought of Bennet as his replacement. “Who’s Michael Bennet?” asked the superintendent.

To Bennet's friends and family, the idea of his becoming a big-city school superintendent seemed nutty. Not only did he have no training or experience in education, he had never attended a public school. Neither had any of his three daughters. Even among experienced superintendents, failure rates were high and tenures short. His longtime mentor, Gov. Celeste, remembers telling Bennet, "If you have any hope of a political career, it's the worst possible thing you could do."

Bennet, however, was intrigued by the challenge. He called up other superintendents, read everything he could get his hands on about school reform, and by the time of his interview with the school board had come to three conclusions: “One, I couldn’t believe how bad urban school systems were doing. Two, I had no idea whether my lack of experience would be a negative or positive. And three, I desperately wanted the job.” He was chosen over a Latina who had been a community college president and the black superintendent of another school district.

The board’s unconventional choice was soon tested when the new superintendent announced a plan to close Manual High School, once the pride of Denver’s African American community. Manual’s enrollment had fallen nearly by half, classroom discipline was weak, gangs ruled the corridors. Even after repeated reform efforts — contracts with parents, performance pay for teachers, “small school” restructuring — 97 percent of Manual’s students were failing the citywide math exam, 90 percent the writing test. Only 20 percent who entered ninth grade actually graduated. Bennet’s proposal was to send students to other schools and start over at Manual with a new principal, new teachers, new students and a new approach to education.

“It was his stake in the ground,” said Allegra “Happy” Haynes, a former city councilor who moved with Bennet from city hall to the schools. “Manual really stood out in terms of how bad it was.”

Not everyone saw it that way. Manual’s teachers felt they were being blamed unfairly for their unruly and unprepared students. Black and Hispanic students felt abandoned. African American leaders saw it as an insult to their community. Students marched on school headquarters, and black ministers denounced Bennet.

Haynes remembers attending a community meeting with Bennet in a packed auditorium with people crying and jeering at him whenever he spoke. “He stood there all night and never once got defensive,” she said. “It was an extraordinarily painful experience for him, but the way he saw it, it was the things that we weren’t doing for these kids that was the real civil rights issue.”

Bennet soon realized that closing the school was only the first step; he also had to make sure that its students would be offered something better somewhere else. He created a spreadsheet to track where all 558 students were going, set up a network of academic counselors to advise them and recruited hundreds of community leaders to serve as life mentors or provide them with part-time jobs. By July, however, it looked as though hundreds of Manual students might simply drop out of school. So for six weeks the superintendent of schools spent nights and weekends going door to door to enroll students in other programs. When schools reopened in September, all but about 100 Manual students were enrolled somewhere else — a higher return rate than in previous years.

At Denver’s other 160 schools, Bennet initiated annual “town meetings” with teachers at every school — four or five per week — to listen to their complaints and suggestions. Every principal was assigned to one of 15 groups that met with the superintendent once a month.

“He’s the only superintendent I know of who spent half of every day with teachers and principals,” said Jaime Aquino, whom Bennet recruited from New York City to be chief academic officer. Central office employees were evaluated on how responsive they were to the schools, rather than the other way around.

In dealing with a sometimes hostile teachers union, Bennet’s strategy was to create allies among teachers open to reform while isolating hard-liners. He pushed bigger pay raises for starting teachers and those willing to teach at low-performing schools. Only after pouring money into enhanced teacher training did he push for more merit pay. Charter schools were incorporated into the public system. And with his support, the Colorado legislature gave teachers at any school the power to opt out of union contracts to gain the flexibility for educational innovation. Today, teachers at nearly 20 percent of Denver schools have voted to opt out.

“He had a lot of credibility with teachers that the union leaders couldn’t ignore,” said Tom Boasberg, a childhood friend from Cleveland Park whom Bennet lured from a telecom company to be the school system’s chief operating officer. Boasberg would eventually succeed Bennet as superintendent.

Michael Casserly, executive director of the Washington-based Council of Great City Schools, credited Bennet with beginning the transformation of one of the country’s most troubled urban systems into one that is now one of the highest performing. According to an evaluation done by his organization, the number of students found to be proficient in reading and math increased by 6 percentage points during Bennet’s four-year tenure, and the upward trend has continued ever since.

Even today, when Bennet visits the city’s schools, teachers and principals come up to give him a hug and reminisce. He still remembers their names and what projects they had worked on together.

“It was the best job I ever had,” he said, almost wistfully, as we sat in his Senate office one evening.

It was just before Christmas 2008 when Gov. Bill Ritter stopped by the Bennet house in Denver. Ritter had a big decision to make. Obama was about to nominate Colorado Sen. Ken Salazar to be secretary of the interior, and it would be up to the governor to appoint a replacement. Ritter wanted Bennet to apply.

“I didn’t think, going in, I would appoint him, but I wanted his name in the hat,” Ritter said. “The others I didn’t have to ask.”

The “others” amounted to a who’s who of Colorado’s Democratic politics, including the outgoing speaker of the Colorado House, the president of the state Senate, a popular congressman and a former U.S. attorney. At the top of the list was Mayor Hickenlooper.

“Michael came over to my House on a Sunday night and said, ‘Listen, if you’re interested, I can take myself out,” Hickenlooper recalled. But Hickenlooper says he was ambivalent: He didn’t really want the job, but he didn’t want some of the others to get it either. So he told his friend to go for it. “To be blunt, I didn’t think Michael had a chance.”

Ritter consulted the White House and Senate leaders and interviewed all the candidates. “The person who stood out was Michael Bennet,” Ritter told me. “We were able to talk through topics ... in a way that made me very comfortable. And, quite frankly, he had a sense of humility.”

Reaction to Bennet’s Senate appointment ranged from perplexed to apprehensive. Sen. Chuck Schumer of New York called Ritter and sarcastically thanked him for throwing away a Democratic seat on an unknown who could not win reelection. Colorado House Speaker Andrew Romanoff threatened to mount a primary challenge. Celeste warned his young protege that he’d known only three people appointed to the Senate, and all of them had failed to hold their seats.

“Once again, he ignored my advice,” joked Celeste.

For the next two years, when he wasn’t trying to find his way around the Capitol or dealing with the financial crisis, global recession and the fight over health-care reform, Bennet invested every waking moment introducing himself to Colorado voters and communities that had never heard of him.

Lynn Bartels, then the leading political reporter for the Denver Post, recalls the road trip she took with Bennet to Colorado’s eastern plains a few months after his appointment. After an unplanned detour into a sunflower field — Bennet was driving — the entourage finally made it to the public library.

“It’s 8 a.m. and he’s droning on like my worst [professor] in college,” Bartels said. “They were yelling at him, ‘Just answer the question!’ And when it was over I said to him, ‘That was the most pathetic performance by a politician I have ever heard.’

“So we go on to the next meeting,” Bartels continued, “and he hits it out of the park.”

In the reelection battle, Bennet lucked out with his opponents.

In the primary, the former speaker, Romanoff, won the backing from the liberal interest groups that make up the core of the Democratic base but in the process wound up reinforcing Bennet’s image as a political outsider. With strong backing from the Obama organization, Bennet won going away.

“The primary toughened him up,” said Mark Udall, then his fellow Democratic senator from Colorado. “He wasn’t fully ready for the rough and tumble.”

In the general election, Republicans fielded a tea party activist, Ken Buck, whose hard-line views on social issues did not sit well with voters in Denver’s fast-growing suburbs. Buck opposed abortions even in case of rape and incest, and in a debate on “Meet the Press” compared being gay to being an alcoholic. The comments allowed Bennet to frame the race as a referendum on Buck rather than one on Obama.

It was among the most expensive and bitter races in a year when Democrats found themselves swimming against the tide. “If nothing else,” Bennet recalled, “I was determined to win just to protect Bill Ritter’s honor.” Bennet raised twice as much money as Buck — being a former business guy turned out to be a big advantage, he discovered — enough to mount a sophisticated get-out-the-vote effort on Election Day. He won by 30,000 votes.

Looking back, Bartels now believes Bennet was the only Democrat on Ritter’s list who could have won that year.

It would be a mistake to look at the arc of Bennet's career and not see the restless ambition and deep well of self-confidence beneath his modest, self-effacing demeanor.

Even among talented and ambitious people, there aren’t many who, without any training or relevant experience, would think to put themselves forward for a job as financial dealmaker, or chief of staff to a big-city mayor, or superintendent of a troubled school system.

“There’s not a whiff of arrogance about him,” said John Belcaster, his law school roommate, “but there is this quiet confidence that he can master almost any new subject.”

Bennet said he inherited his confidence from his father, whose peripatetic career provided a model for “trying things you don’t know much about.”

“Dad didn’t push us in any direction — he just set a powerful example,” said Bennet’s brother, James, the longtime editor of the Atlantic who was recently named editorial page editor of the New York Times.

“Michael grew up in a family where making a difference was important and there were high expectations about what you do with the opportunities that are given to you,” explained Udall, who grew up in a similar household. “He doesn’t hide his ambition, but he integrates it with this wonderfully wry sense of humor and an incredible work ethic.”

I asked Bennet whether he considered himself ambitious. Yes, he replied, but not in the way people usually think of ambition.

“If you look at my career, it’s not been about plotting how to grab the brass ring or move up to the top of the ladder,” Bennet said. “I took jobs that a lot of people in similar situations wouldn’t have taken — in fact, a lot of them said I was crazy. And yet every one of those jobs powerfully informed the next job, or the one after that, in ways that I, certainly, could have never predicted.”

“A lot of life is improvisational,” he said. “You do what you can when you can.”

There is, however, more guile behind all that improvisation than Bennet lets on or wants to admit.

It was Bennet, for example, not Hickenlooper, who first broached the idea of becoming the new mayor’s chief of staff. And once his name was floated for school superintendent, Bennet wasn’t shy about mobilizing his network of political connections to get it. His allergy to national media coverage not only reflects his distaste for mindless sound bites, it’s also part of a careful strategy of someone who is not a native Coloradan to be seen as focused on Colorado issues rather than Washington’s partisan squabbles.

That “not from here” vulnerability is one his Republican opponents are eager to exploit.

“‘Coloradan’ is not a word I’d use to describe Michael Bennet,” said Jon Keyser, a former Air Force intelligence officer and state representative who is a candidate in this month’s Republican primary. “We’re a bit more rugged, more matter of fact in the way we deal with each other.”

Bennet can also be a shrewd player of the inside game. When pressed by party leaders to serve as chairman of the Democratic campaign committee, he agreed only after extracting a promise of a coveted seat on the tax-writing Finance Committee, jumping the queue ahead of more-senior colleagues.

“Michael likes to think that he is post-partisan, that the partisan process is beneath him,” Keyser said. “But beneath that veneer he’s a true-blue liberal who votes with his president and his party.”

“Is he representing the state or is he representing the interests of the Democratic Party and his own career?” asks Jack Graham, a retired businessman and former Colorado State University athletics director who is also vying for the Republican nomination.

Earlier this year, when Bennet’s name showed up on insiders’ short list of possible vice presidential picks for Hillary Clinton, he took pains to discourage the speculation. But to anyone familiar with Bennet’s knack for making his own luck and creating opportunities, the possibility of a presidential campaign came as no surprise.

If winning his first Senate election was a high point for Bennet, the low point came a few months later when he returned to a Capitol that was even more dysfunctional than ever. His party had lost control of the House while barely holding on to control the Senate. Almost immediately, both sides settled in for another two years of manufactured crises, endless posturing and partisan stalemate. The few decisions that were made were done at the last minute by the president and a handful of party leaders, with little input from individual senators.

For Bennet, who got his first taste of the Senate in high school as a Senate page, it was the beginning of what one aide called a “dark and gloomy phase.” He was uncharacteristically brooding, frustrated, unmoored. When in Washington, he couldn’t wait to get back home to Susan and the girls in Denver.

“I got to the point where I was referring to this place as the Land of the Flickering Lights, because the standard of success was that we kept the lights on for another two months,” he told me.

Eventually, staff and colleagues were able to talk Bennet out of his funk. “Who’s gonna have sympathy for a whiney U.S. senator?” Mark Warner (D-Va.) recalls asking his close friend and Senate ally. “Good legislators have learned patience. Michael’s still in the process of acquiring it.”

With Warner’s help, Bennet wheedled his way onto a bipartisan group of senators crazy enough to try to hammer out a long-term budget deal. Although the Gang of Eight met in secret for months, it never was able to agree on crucial details of tax increases and cuts in entitlement spending that had stymied all such previous efforts. In the end, the effort collapsed under pressure from party leaders who vowed to do whatever was necessary to prevent other senators from signing on.

“Nobody here is really serious about the budget — it’s too politically useful not to be serious,” Bennet told me. Democratic leaders, he said, “want you to think that we are all that stand between you and having your Medicare taken away. Republicans want you to think that we are all that stands between you and a tax increase.” Because budget stalemate reinforces both messages, “the whole institution has now habituated itself to kicking the can down the road.”

In time, Bennet has learned to take satisfaction in smaller victories. “Some weeks it feels like it’s 100 percent a waste of time,” he said, “while other weeks it feels like it’s 100 percent useful. It ebbs and flows.”

As a member of another eight-member gang — this one involving immigration reform — Bennet took the lead in crafting the agricultural worker portion of the bipartisan bill that eventually passed the Senate with 68 votes. (It was all for naught: The Republican leadership never let it even come up for a vote in the House.) He worked with Republican Richard Burr of North Carolina in pushing through legislation allowing expedited approval of lifesaving drugs that show promise in early trials. And in the long-running battle over reauthorization of the No Child Left Behind education law, colleagues give the former school superintendent credit for finally convincing Democrats that the federal role in education had become overbearing and inflexible while convincing Republicans of the imperative to hold states accountable for poor-performing schools.

“He bridged the gap with the Republicans,” said Sen. Patty Murray, ranking Democrat on the Education Committee, who called Bennet “the pragmatic voice of reason.”

For Bennet, the education bill was something of a bittersweet victory. The eight years it took to pass it, he said in yet another speech to an empty chamber in December, revealed a disturbing lack of urgency on the part of too many of his colleagues who were “content to treat America’s children as if they are someone else’s rather than their own.” The same outcome, he told me later, could have been had years earlier if party leaders had simply given their members the green light to compromise.

It is not uncommon for Bennet to find himself at odds with party leaders. At the twice-weekly caucus lunches, Bennet often chafes in silence as Democratic leaders plot their latest partisan maneuver or exhort senators to stay “on message.” Although disinclined by temperament to be the constant critic or lead ill-fated rebellions, he has challenged the leadership on a few occasions. That he prevailed, a number of senators told me, is a measure of the respect he has from his colleagues.

“I have heard him give speeches in caucus, off the cuff, and turn the issue 180 degrees,” said Sen. John Tester of Montana, a friend and frequent foosball rival.

“He wants us to be less political and more focused on the issues,” said Schumer, who will takeover as Senate Democratic leader next year and shows no sign of becoming less political.

Schumer, by the way, long ago called back Ritter to admit he’d been wrong about Bennet. He now calls him “an ideal senator.”

Steven Pearlstein is a business and economics writer for The Post. He is Robinson Professor of Public Affairs at George Mason University. To comment on this story, email wpmagazine@ washpost.com or visit washingtonpost.
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