DENVER — Colorado politicos still remember where they were on Jan. 3, 2009, the day Gov. Bill Ritter rocked the state by naming a little-known school superintendent named Michael Bennet to the Senate seat vacated by Ken Salazar.

“That caught everyone by surprise,” recalled University of Denver political science professor Seth Masket. “I was one of those watching the political scene at the time, and everyone had a shortlist of who was likely to get picked. He was on no one’s list.”

It was a Cinderella start to what has been a charmed political career — until now. After jumping into the Democratic presidential primary race in May, the two-term senator is scraping the bottom of the field, failing to qualify for the September and October debates while raising just $2.1 million in the third quarter.

Even so, Mr. Bennet vowed this week to stay in the race at least through the Feb. 11 New Hampshire primary. His strategy: Convince voters that his more moderate platform and success in winning “two tough national races” in Colorado makes him the best candidate to defeat President Trump in 2020.

“I didn’t win two swing-state elections by apologizing for Obamacare, or making empty promises,” said Mr. Bennet in an Iowa television ad released Thursday. “I did it by going everywhere, offering ideas that can win broad support, even the places that don’t vote for me. You want to beat Trump? That’s how.”

In fact, the 54-year-old Bennet’s political rise may be attributed to a heady mix of persistence, purpose and privilege.

Mr. Bennet arrived in Colorado in 1997, but he grew up in Washington, D.C., in a politically prominent family. His father Douglas Bennet served as an ambassador, an assistant secretary and headed National Public Radio. His brother James Bennet was the editor-in-chief of the Atlantic before becoming editorial page editor of The New York Times.

In Colorado, Michael Bennet landed a plum job with Philip Anschutz after a Wesleyan University trustee, Alan Dachs, wrote to the billionaire on Mr. Bennet’s behalf, even though he admitted to Mr. Anschutz that “he knew little about numbers, let alone Anschutz’s massive [business] empire,” according to a 2010 article in the Denver Post.

In 2003, he connected with then-Denver Mayor John Hickenlooper, a fellow Wesleyan grad, and became his mayoral chief of staff. From there he went on to become Denver Public Schools superintendent, despite having no background in education.

Why Mr. Ritter plucked him from a field that included Mr. Hickenlooper for the Senate seat is still debated — the governor called him “accomplished” and “highly competent” — but the rumor mill had it that Mr. Bennet nailed the interview and was the choice of the Obama team.

“He was known among political types like the Obama people,” said Denver pollster Floyd Ciruli. “His brother is a very major player in Washington. That’s his milieu and his background, and he excels at that: being recognized as a talent. Obama, in my view, was the person who did the most to tell Ritter, ‘This is the way to go.’ “

After winning the Senate jackpot, Mr. Bennet entered a tough 2010 pro-Republican election cycle, fueled by the rise of the tea party and Obamacare backlash. Despite having never run for office, he showed unexpected toughness, not shying away from GOP strongholds.

“The thing about Bennet is that he shows up,” said John Swartout, executive director of the Colorado Counties Inc., a Republican who worked on the campaign of Mr. Bennet’s 2010 Senate foe, Ken Buck.

“During the Obamacare mess and everything else, he was having town meetings in small Eastern Plains counties and on the Western Slope,” Mr. Swartout said. “He would go where he was most unpopular and get yelled at by people. And it was kind of odd, because he’d say, ‘I didn’t really agree with the stimulus package,’ and people were saying, ‘Yeah, but you voted for that.’ But he kept getting out there.”

Early on, Mr. Buck led in the polls, but his gaffes came back to haunt him, notably his comment on NBC’s “Meet the Press” comparing homosexuality to alcoholism. Mr. Bennet eked out a narrow victory.

In 2016, Republicans nominated Darryl Glenn, a likeable but little-known El Paso County commissioner whose lackluster, ill-funded bid stood little chance against the well-oiled Democratic campaign. Mr. Bennet won by 50% to 44%.

Did Mr. Bennet win “two tough national campaigns”? Not in the opinion of former Colorado GOP chairman Dick Wadhams.

“Buck made some terrible mistakes that got Bennet back into the race and allowed Bennet to win,” Mr. Wadhams said. “And then six years later, the Republican Party nominates somebody, Darryl Glenn, who ran a hapless campaign. There was no campaign. They [Democrats] were lucky.”

Mr. Bennet may have received some help from Republicans, but he also showed himself to be a disciplined campaigner who avoided self-inflicted wounds.

“He has a political style that has worked fairly well for him here, and he’s one of the candidates who hasn’t really embarrassed himself on the campaign trail,” Mr. Masket said. “People who have seen him, people who have met him tend to come away with a good impression of him. People wish him well.”

What missteps he has made haven’t held him back. He headed the Democratic Senatorial Campaign Committee during the 2014 election, which despite his efforts saw his party lose nine seats and control of the Senate.

During his tenure as superintendent in 2008, DPS entered into an “exotic transaction” to raise $750 million that wound up putting the district deeper in debt, according to The New York Times, although Mr. Bennet has defended the deal, saying it saved the district $20 million and no one could have predicted the credit crisis.

Analysts say Mr. Bennet is unrivaled in one-on-one interviews, but lacks the big, charismatic personality of, say, a Pete Buttigieg, that wins over large crowds and television audiences. That may be in a problem on the Iowa campaign trail.

“His strength is not retail politics,” Mr. Ciruli said. “I thought he did well at the [July] debates, although he did not excel. And he’s not a great platform speaker. But he does an incredible interview, and he’s tenacious. He’s a quick learner. And that’s served him well in Colorado.”

As for the presidential primary, Mr. Bennet’s increasingly slim chances are tied to those of former Vice President Joseph R. Biden. An early Biden exit would create an opportunity for Mr. Bennet to command the center lane, and just maybe recapture some of the magic that launched his political career.

“Were Biden to decide to drop out of the race, and you had a lot of more moderate voters looking for a candidate, he might look a lot more interesting to people,” Mr. Masket said. “But as long as you have that very big fish in the sea, it’s hard for him to get attention.”

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