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Can the Bennet brothers save the Establishment?

Michael is running for president. James is a top editor at the New York Times. Both are struggling to figure out their place in an altered landscape.

Left: Sen. Michael Bennet (Colo.), a Democratic presidential candidate, speaks to reporters in Sioux City, Iowa, after a campaign stop. (Scott Olson/Getty Images) Right: James Bennet poses for a portrait in October 2009, while serving as editor of the Atlantic magazine. He is now editorial page editor at the New York Times. (Susana Raab)

For all the scandals, screw-ups and controversial hires, James Bennet’s colleagues at the New York Times generally like working with him. James, who oversees the editorial page and is rumored to be a candidate to run the newsroom after Executive Editor Dean Baquet steps down, has a reputation for being intelligent, loyal and deft with a red pen. Still, earlier this year, he had a habit of picking up his cellphone and disappearing at the worst possible time — Friday evenings, when his team was closing the section. Was he talking to You-Know-Who?

“I’m 1,000 percent sure it was Michael,” said one of James’s co-workers, who spoke on the condition of anonymity to discuss the boss.

Michael F. Bennet: the Democratic senator from Colorado, soon-to-be candidate for president and James’s big brother.

When James was editor of the Atlantic magazine, the company changed its ethics guidelines to allow him to donate to his brother’s Senate campaign. In addition to giving $2,400 to both the primary and the general, he’d sit in on messaging phone calls, tweak speeches and occasionally travel to Denver. (However, he would not touch any of the magazine’s coverage of the campaign).

About the series
An occasional series examining 2020 candidates through the prism of their most important relationships.

“How are you not going to let him give to his brother?” Atlantic Media Chairman David Bradley said.

This would never fly at the Times. And so months before Michael’s May 2 announcement, James and one of his deputies headed to the office of A.G. Sulzberger, the recent inheritor of the Gray Lady, and said that if his brother were to run, then the opinion editor would agree to recuse himself from 2020 coverage.


Sen. Michael Bennet (Colo.) greets Pat Fitzgerald during the Iowa Democrats' Passport to Victory event at Johnson's Supper Club in Elkader, Iowa. (Eileen Meslar/AP)

It would be tough to take himself off the biggest story in the country, but James supported his brother’s (probably quixotic) quest because, in a way, they were on the same one.

You wouldn’t know they were related by looking at them (James is bald, bearded and has expressive eyebrows; Michael has a head full of parted hair, and a clean shave that showcases a crooked smile). But they share a voice — deep and slow, almost a perfect parody of a rich person, as if they speak only while swirling a martini — and they use it to preach the same things: civility, bipartisanship and reasoned discourse.

The Bennets are the anti-Trump dynasty, institutionalists at a time when their very institutions — Capitol Hill, the mainstream media — have come under attack.

To their critics on the left, they are mealy-mouthed centrists, focused on giving a platform to “both sides,” for whom “civility” is just another cudgel used by elites to cling to power.

To their friends and supporters, they are what a politician and a newspaperman are supposed to look and act like, brothers in the mold of the Kennedys, idealists fighting for what’s right.

“Are they dinosaurs or are they the future?” their lifelong friend Eric Kolodner said. “I’m worried that it’s the former.”

Both Michael, 54, and James, 53, declined to comment for an article about their relationship. But at a lunch in 2017 with a group of journalists, Michael acknowledged that he and his brother were struggling to figure out their place in a newly altered landscape.

“We’re asking the same questions now,” he said. “What’s his role? What’s my role?”

He didn’t have the answer.


Michael Bennet speaks to his wife, Susan Daggett, just before being sworn in as the junior senator from Colorado on Capitol Hill in 2009. (Melina Mara/TWP)

The Bennet brothers and their younger sister, Holly, grew up in a tony neighborhood in Northwest Washington, blocks from St. Albans, the prep school both attended in the early 1980s. Their mother, Susanne, was the daughter of Jewish art dealers who had managed to get her out of the Warsaw ghetto in the 1940s and into Wellesley College. Their father, Douglas, was an executive at an array of respectable institutions: the U.S. Agency for International Development, NPR.

Douglas was the boys’ ultimate role model, and from him they learned the art of political discourse, acquired a love of sailing (when James was at the Atlantic, he once sold a boat to a friend, and according to a colleague, missed it so much that he would sit at his desk and watch it on a “marina-cam” live stream) and gleaned lessons about proper decorum in polite society.

“Dad’s way was to instruct by barely perceptible guidance and demonstration. When he was teaching us to row, he would sit in the stern of the dinghy with his hand resting on his lap always pointing toward the goal, so that we could see, without turning our heads, when we were wandering from the right path,” Michael said at a memorial service held in his father’s honor earlier this year. "As in life, we could tell whether we were headed the right way just by keeping an eye on Dad.”

When Douglas became the president of Wesleyan University in the mid-1990s, he tried to bring some of his lessons to campus by banning students from using chalk on the sidewalks — a decades-old tradition — because too many of their scrawlings didn’t “meet the civility test.”


Douglas J. Bennet, Michael and James's father, was president of Wesleyan University from 1995 to 2007. He was previously a federal policymaker, assistant secretary of state and president of NPR.

As St. Albans boys, his sons would pass any such test. The school prided itself on being a molder of Great Men. It demanded excellence, and James, a year younger and a class behind his brother, excelled under these conditions. He played varsity baseball, ran the school paper, got top grades.

Michael, on the other hand, “hit his growth spurt late,” said John Schafer, a childhood friend.

Michael’s report cards were fine, but nothing to brag about. And as a little guy on campus, he was never afforded the social cachet that came with being good at sports. He had a goofy nickname of mysterious origin, Flobie, and was teased about the size of his ears.

“James was this fully-bloomed rose,” said Kolodner, a classmate who grew up next door, “and Michael was a plant that no one knew what was going to happen with.”

But Michael did have fight. It sometimes seemed like every neighborhood football game ended with him wrestling his brother into the mud.

And despite being a bit of a pipsqueak on campus, Michael seemed convinced that he was capable of extracting justice from an unjust world.

Schafer remembers a time he shoved Michael into a locker, demanding that he apologize for something (he forgets exactly what).

“He adamantly refused to do it,” Schafer said. “Instead, he’s in there just yelling about what he called ‘The One-Punch Theory.' ”

All it would take, Michael hollered, was one strategically placed blow and he would be able to knock Schafer out.

Schafer listened to Michael rage, then quietly unlocked the locker and left to go watch a baseball game.

It’s unclear how long Michael stayed in there begging for a fight. No one was left to listen.


In January 2009, Michael Bennet is sworn in as the junior senator from Colorado with his wife, Susan Daggett, and their daughters, Caroline, 9, left, Halina, 8, left, and Anne, 4, far right, being held by Vice President Joe Biden by his side. (Melina Mara/TWP)

Michael may have been a late bloomer, but he did bloom. He went to Wesleyan, his father’s alma mater, followed by Yale Law School. He married fellow Yale alum Susan Daggett and headed out West — first making millions working for Philip Anschutz — a Colorado billionaire who got rich off investments in oil and railroads — and then, eventually, getting into politics.

He landed a job as Denver Mayor John Hickenlooper’s chief of staff and later as a schools superintendent. His time turning around a failing school district earned him a reputation as a reformer and a profile in the New Yorker (written by Katherine Boo, a longtime friend of James), and in 2009 he was appointed to the U.S. Senate by Colorado Gov. Bill Ritter.

“I really still don’t know why Ritter made such an unusual appointment,” Bennet wrote in “The Accidental Senator,” a chapter of his political memoir.

He arrived with some hope of tackling the big issues facing the country in a bipartisan way, and instead joined one of the least-productive Senates in the nation’s history.

In a 2014 floor speech, the Senate chamber nearly empty, Michael offered a searing critique of his colleagues and the institution: “You can see this corruption in the difficult decisions we avoid. 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.”

By this point, James was deep into a journalism career that was anything but accidental. He’d worked his way up through his first tour of the New York Times: metro desk, White House correspondent, Jerusalem bureau chief. Then David Bradley, who was searching for a new editor to run the Atlantic, came calling.

James wasn’t an obvious choice. Bradley said he was looking for a candidate with a nonpartisan streak, and James told him he’d never once voted Republican. But Bradley liked him anyway.

“It was like talking to a ‘Mr. Smith Goes to Washington’ character,” Bradley said. “You just know somebody had raised him to brilliant 1920s standards. And I don’t mean anti-woke, by the way, I mean integrity and honesty and virtue.”

James got the job in 2006 and hired an impressive and diverse set of writers, including Ta-Nehisi Coates, Andrew Sullivan and Matthew Yglesias. The magazine became known for publishing cover stories about big ideas: “Why Women Still Can’t Have It All,” “The Case for Reparations,” “Is Google Making Us Stupid?” Website traffic skyrocketed and the Atlantic returned to profitability.

The Bennets were reaching ever higher levels of success, and would joke, one of James’s former colleagues said, about which one of them would have the better headstone.

But the competitive streak that led to fights on the football field, this was not. They reveled in each other’s accomplishments. They were devoted to family and to the institutions that promoted them. And yet, remaining loyal to both could sometimes make things complicated.


James Bennet hired impressive writers, including Ta-Nehisi Coates, Andrew Sullivan and Matthew Yglesias, after he became editor of the Atlantic magazine in 2006. Website traffic skyrocketed and the magazine returned to profitability.

In early 2014, Atlantic magazine contributor Caitlin Flanagan turned in a draft of a year-long investigation of the state of fraternities in America. It began with fireworks (ignited, with predictable results, in a frat brother’s rear end) and continued on with tales of excessive drinking and sexual assault.

The article included the story of a female student who was raped at a Wesleyan University party, and the ugly court battle that followed — during which the college tried to defend itself against a lawsuit by blaming the woman for putting herself in an unsafe situation. Douglas Bennet, who was not president of the college at the time of the sexual assault or the subsequent court case, was mentioned in the story only in passing, as Flanagan recounted Wesleyan’s inability to rein in a problematic fraternity culture.

James has been known to be a bit moody — a “heavy sigher,” said one colleague, occasionally “imperious,” said another (both said it never affects his editorial judgment). And stories published about his relatives have proved to be something of a trigger for him — pulling taut his dueling devotion to the people he loves and the institutions he holds dear.

A few years earlier in James’s tenure at the Atlantic, when he was also helping out on his brother’s Senate campaign, the New York Times ran a story about Michael’s political race that James thought had been unfair to his brother. It sent him into a fit of rage.

“He was apoplectic,” one of his former colleagues said.

In the case of the Flanagan story, James had particular reason to be sensitive. Around that time, Douglas had been in and out of the hospital, dealing with complications from a fall that would eventually take his life. To his colleagues, it seemed clear that he cared about his father’s legacy.

James agreed to recuse himself from any role in editing the story, but Jennifer Barnett, the managing editor at the time, said in an interview with The Post that “over the course of producing the story, he abused the staff and undermined the editorial process.”

According to Barnett, James mistreated Scott Stossel, the editor in charge of the story, often in “hard-to-detect ways,” such as not inviting him to staff gatherings, ignoring his emails and cutting him off when speaking in front of colleagues.

When reached to comment, Stossel, who still works at the Atlantic, said in an email:

“James, with whom I worked for a decade, was an excellent, highly principled editor-in-chief and I’m very proud of the journalism we produced under his leadership. In this particular situation, circumstances put James into an impossible position, so he was recused from working on that piece, which we published as a cover story, to general acclaim.”

Barnett said she reported James to human resources three times during the episode. In an email, she told Scott Havens, who was then president of the Atlantic, that James had been acting “openly hostile” toward Stossel. It was “affecting every aspect of the magazine production,” she wrote, “and is quite literally making me ill.”

“Hi Jennifer, thanks for reporting this,” Havens wrote back. “Please know I’m also aware and involved.” (Havens declined to comment for this article.)

After the story published — without any changes made by James — James called the managing editor into his office.

“He told me to ‘be very careful,’ ” Barnett said. “That he was ‘in this for the long game.’ ”

A short time later, James was promoted to co-president of the Atlantic and eventually lured back to the New York Times. But not before Barnett left journalism.

“I quit because of him,” she said — adding that it wasn’t only the fraternity story but the atmosphere James created.

“I’m astonished and very sorry to hear this, but there’s no way I can defend myself — I’ve said I would recuse myself from anything related to my brother’s campaign, and this [Washington Post] article clearly falls into that category,” James wrote in an email when asked to comment.


James Bennet, editorial page editor of the New York Times, leaves federal court in New York where the Times was being sued by Sarah Palin over an editorial he helped write that linked right-wing political rhetoric to the shooting of Rep. Gabrielle Giffords (D-Ariz). (Larry Neumeister/AP)

There’s a joke about the Bennets, that their greatest struggle is making sure their name is spelled correctly. It’s usually made by their friends, but two years ago, James was grilled about it in court.

“What accounts for the fact,” asked the wisecracking judge, “that neither you nor your brother nor apparently your parents know how to spell ‘Bennett’?”

James had been called as a witness in a defamation lawsuit that Sarah Palin, a former Alaska governor and 2008 vice presidential nominee, filed against the New York Times regarding an editorial that had falsely claimed that an ad her PAC had run in 2011, featuring congressional districts in “stylized crosshairs” (i.e. gun sights), was linked to the shooting of Rep. Gabrielle Giffords (D-Ariz).

James had written the faulty language, and Palin’s lawyers argued that his relationship with Michael had something to do with it. They grilled him on it:

Mr. Bennet, your brother Michael F. Bennet is a senator in Colorado, right?

Two days before the Tucson shooting, his office was threatened, was it not?

Do you recall that Sarah Palin endorsed your brother’s opponent?

James’s three-year tenure as editorial page editor has been pockmarked with embarrassments. These have ranged from singular screw-ups like the Palin editorial (which he has called an “honest mistake” — the case is ongoing) to rolling outrage over the provocative work and extracurricular peevishness of Bret Stephens, a conservative columnist who recently used the occasion of a professor calling him a “bedbug” on Twitter to write a column about the dehumanizing language of the Nazis. That column sent Twitter into a tizzy (“#Bretamorphosis”), but its content didn’t catch James by surprise: Not only had he seen it before publication, Stephens said, he’d helped edit it.

“After that whole thing erupted, James and I went out for a very friendly drinking session,” Stephens said. “His line was: ‘We seem to be approaching peak Twitter insanity.' ”

In James’s eyes, Stephens and his conservative takes are a feature of a healthy newspaper, not a … bug.

“I think if we show we take conservatives seriously and we take ideas seriously … we get a lot more moderates paying attention to what the New York Times has to say,” he said in a staff meeting, according to audio obtained by HuffPost.


James Bennet interviews Facebook chief executive Mark Zuckerberg in 2013. As editor of the Atlantic magazine, Bennet was credited with publishing cover stories about big ideas. (Win McNamee/Getty Images)

It’s not exactly a foolproof play for a broader audience, and James has also said that there are “tremendous rewards” for telling liberal audiences what they want to hear, and there can be “tremendous punishment for confounding their expectations." But it’s worth the possible subscription cancellations, he argues, if the alternative is predictability.

“I do worry we are living in an age of a new kind of radical conformity,” he said in a discussion at the Shorenstein Center at Harvard earlier this year.

His critics think this idea is absurd: “He’s trying to create a politics that doesn’t really exist, with civil debate among Democrats and a kind of respectable conservative that only exists on an op-ed page,” said Alex Pareene, a staff writer at the New Republic. “It’s comforting, but it’s a fantasy.” His boss, Sulzberger, on the other hand, seems to appreciate the mission.

“It’s increasingly hard to find places where diverse voices debate ideas respectfully and thoughtfully. But that’s exactly what James believes is needed and it’s what he’s building,” Sulzberger said. “Under his leadership, Opinion has been vital, creative and unafraid to tackle big issues, from privacy to domestic abuse to the legacy of slavery. He’s not only a great editor, but a deeply honorable one. As much as any journalist I’ve worked with, he’s constantly pushing himself to make the right journalistic decision.”

Last month, members of James’s staff were asked to fill out a job evaluation for him, which they believed had something to do with the fact that Baquet will be stepping down as executive editor in the next few years. Only a handful of editors are being evaluated this way, and James has a lot to boast about. His section won a Pulitzer for Brent Staples’s searing coverage of race in America, the page has a stable of new, interesting writers that even his critics tend to like (Jamelle Bouie, Michelle Goldberg, Kara Swisher) and members of his staff speak of his editing chops with reverence.

Other senior Times editors said to be in contention to succeed Baquet are: Joseph Kahn, Carolyn Ryan, Clifford Levy and Rebecca Blumenstein.

“If the decision were made tomorrow, I would put my money on it being James,” a senior editor said.

Michael’s path to Top Job is harder to foresee. In a time not long ago, it would be easy to imagine him as a formidable presidential candidate: popular purple-state senator who boasts a bipartisan streak (member of immigration reform’s Gang of Eight) while also being a team player for Democrats (former chairman of the Democratic Senatorial Campaign Committee).


Sen. John McCain (R-Ariz.), right, shakes hands with Rep. Joe Courtney (D-Conn.) as Sen. Michael Bennet (D-Colo.) looks on after a news conference to announce their introduction of the Post-9/11 Troops to Teachers Enhancement Act at the Capitol in October 2009. (Chip Somodevilla/Getty Images)

As a senator, he has done yeoman’s work — helping craft farm bills, overhauling No Child Left Behind and fighting for transparency in political donations. A lesson he has learned from being part of a do-nothing Senate is not to blow it all up: He doesn’t support nuking the filibuster or push for the most-progressive legislation. He opposes Medicare-for-all and didn’t sign onto the Green New Deal, telling the Atlantic that he doesn’t want the “Twitter base of the Democratic Party” to decide what’s important. By today’s standards, he might be considered a moderate, certainly in temperament.

“The founders of our country did not believe that we would agree with each other,” Michael said at a recent event in Austin, when asked whether “civility” is a worthy goal at a time of heightened public discourse. “And out of those disagreements they genuinely believed we would fashion more imaginative and more durable solutions than any tyrant or king could come up with on their own.”

Michael’s most notable moment in the campaign has been telling voters — exhausted by today’s reality show presidency — that a Bennet presidency would be so normal that they’d be able to forget he existed for weeks at a time. Polling around zero percent, he seems to have been forgotten by most people already.

But he hasn’t given up. Just last week, Michael was in New Hampshire, telling a group of voters that he’s just as viable as any Democrat who has made it onto the debate stages that he has missed. For proof of his mettle, he told them to watch a floor speech he gave last year, in which he excoriated Sen. Ted Cruz (R-Tex.) for crying “crocodile tears” over a government shutdown.

“I think it will give you a sense of my capabilities to push back on someone who needs to be pushed back on,” he told the crowd.

One punch. That’s all a young Michael F. Bennet thought it would take to knock out a bully. But if he’s going to test that theory against the president, he needs to figure out how to get out of the locker.


During a presidential campaign swing through South Carolina, Michael Bennet addresses attendees at the Blue Jamboree in North Charleston. (Brian Blanco/Getty Images)

If he does break free, what would that mean for his brother? Unlike the Trump family, the Bennets take the issue of recusal seriously, and as long as Michael is in the race, James will let his deputies handle campaign coverage.

“I’m a little worried,” James joked at the Shorenstein Center earlier this year, “this could expose my irrelevance.”

He was kidding, of course. The Bennets hope and believe that there is a place for their kind of leadership, their kind of moral rectitude, even in a country that elected Donald Trump president.

“I’ve always believed,” James wrote after the editorial board came out in support of an impeachment inquiry, “that strong institutions, like strong families, are meant to transmit principles across generations.”

Photo editing by Moira Haney. Copy editing by Carrie Camillo. Design by Beth Broadwater.

Credits: Ben Terris

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