When Michael BennetMichael Farrand BennetSome realistic solutions for income inequality Democratic senators kneel during moment of silence for George Floyd 21 senators urge Pentagon against military use to curb nationwide protests MORE arrived in Denver in the late 1990s in search of a job, he reached out to a fellow Wesleyan alum, a budding businessman whose craft brewery was starting to take off. That businessman, John HickenlooperJohn HickenlooperGun control group rolls out first round of Senate endorsements The Hill’s Campaign Report: Republicans go on attack over calls to ‘defund the police’ Hickenlooper ethics questions open him up to attack MORE, didn’t bother to return his calls.
They eventually connected, and when Hickenlooper became Denve’s mayor, he hired Bennet away from a high-paying job with the billionaire Republican donor Phil Anschutz to be his chief of staff.
For the next decade and a half, the two men have operated together at the highest levels of Colorado politics.
Between shared Thanksgiving dinners, Hickenlooper pushed Bennet to take the top job running the Denver Public Schools; they competed for an appointment to the U.S. Senate, which Bennet won; and they shared the campaign trail in 2010, when Bennet kept his seat and Hickenlooper won the governorship.
On Thursday, they will share the stage at the first Democratic presidential debate in Miami, a former boss and former employee both struggling to break into the top tier.
In many states, prominent political leaders often clash, matching monumental egos and battling for supremacy even if they represent the same party.
But nearly a dozen sources close to both Hickenlooper and Bennet say they have coexisted peacefully and productively, and that they even consulted each other about their dueling presidential campaigns. Several former aides described their relationship as brotherly, marked at times by friendly competition.
“It’s easy to coexist, because there’s a lot of respect on both sides. I think they wish each other well,” said David Kenney, a prominent Denver lobbyist who is close with both men. “It hasn’t become the Hatfields and the McCoys.”
It may help that the two men have vastly different personalities.
Hickenlooper, a scientist who built one of the first microbreweries in what is now the trendiest beer scene in America, is an extrovert.
Bennet, a Yale-educated lawyer, is more often a behind-the-scenes introvert, who rarely demonstrates the flash of a press-the-flesh politician. Several people who know him said they were surprised by a speech he gave on the Senate floor castigating Sen. Ted CruzRafael (Ted) Edward CruzSenate advances public lands bill in late-night vote The Hill’s Morning Report – Trump’s public standing sags after Floyd protests GOP senators introduce resolution opposing calls to defund the police MORE (R-Texas) that subsequently went viral.
“The Cruz floor speech that went viral was one of these moments, it surprised a lot of people,” said Douglas Friednash, who served as Hickenlooper’s chief of staff when he was governor. “I had not seen that side of Sen. Bennet.”
When the viral clip vaulted Bennet into the presidential conversation, Bennet called his old boss. Neither man tried to dissuade the other from running, according to three people with knowledge of the call.
They have rarely mentioned each other in interviews, though when they do they offer telling insights into their relationship. Hickenlooper, asked about Bennet, told NBC News that they “had very different lives.”
“He was a lawyer, super smart, super talented, super committed. But he’s been mostly in Washington, he spent a few years working in private equity,” Hickenlooper said. “I was a scientist, and I worked professionally as a geologist. I was out of work a few years, that’s relevant, then I opened a brewpub long before people knew what they were.”
“I transformed a community by getting everyone to get to work together, was a top-5 big city mayor in America and then one of the top governors in America,” he also said.
Bennet, asked in a CNN town hall event how he would change the relationship between minority communities and police departments, reached back to his tenure working with Hickenlooper — and several former Bennet aides cringed when he gave Hickenlooper the credit.
“In the old days, after I was in the private sector and before I was a school superintendent, I went to work for the city and county of Denver for a guy named John Hickenlooper. I don’t know whatever happened to that guy,” Bennet said as the audience chuckled. “The first thing we encountered really when he was taking office is a young man named Paul Childs had been shot in Denver by the police department under circumstances that should never have happened.”
“And as a result of that, I worked for a year and a half to completely redo the police oversight system in the city and county of Denver, on John’s authority, it should be said,” Bennet said.
Many Colorado Democrats say they would be happy if either Hickenlooper or Bennet catches fire in the coming months. Donors unwilling to choose between the two have been keeping them both afloat.
“Personally, it makes me sad. Secondly, it’s expensive for all of us. They’re both really, really good men. I would be happy to see either one of them come out of the primary,” said Roxane White, who reported to Bennet as the head of Denver’s human services department and served five years as Hickenlooper’s chief of staff. “We’re way too early to be choosing sides. I’m a donor to both.”
One factor that may help keep the relationship between Bennet and Hickenlooper harmonious is their relative standing in the polls.
On the debate stage Thursday, former Vice President Joe BidenJoe BidenHillicon Valley: Biden calls on Facebook to change political speech rules | Dems demand hearings after Georgia election chaos | Microsoft stops selling facial recognition tech to police Trump finalizing executive order calling on police to use ‘force with compassion’ The Hill’s Campaign Report: Biden campaign goes on offensive against Facebook MORE and Sen. Bernie SandersBernie SandersThe Hill’s 12:30 Report: Milley apologizes for church photo-op Harris grapples with defund the police movement amid veep talk Biden courts younger voters — who have been a weakness MORE (I-Vt.) will stand at podiums in the middle, given their prominent standing in the polls. Bennet and Hickenlooper will be relegated to the wings, reflecting their 1 percent support in just a handful of surveys.
“I don’t think today they view each other in an adversarial way,” Friednash said. “Maybe part of that is, at this point, they’re both long shots.”
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