The Gen X Minnesotan reasoned that the San Franciscan had been at the top too long and Democrats needed some fresh blood in House leadership. In the private sector, he argued, people rarely serve for two decades in top posts.

Phillips ultimately backed Pelosi (D-San Francisco) for speaker as part of a deal that saw her leave leadership last year. But in the spring of this year, as another Californian, Sen. Dianne Feinstein, began missing votes, he spoke out again, writing an op-ed arguing that she needed to resign for the good of the country.

Feinstein’s refusal to resign — she died in office on Sep. 29 — did the country a disservice, Phillips told The Times during a visit to California last month.

“Who doesn’t know Congress is dysfunctional, but I did not know how horrifyingly so until I got there,” said Phillips, 54. “I encountered a culture filled with people who had been there for decades, that were so clearly focused more on the preservation of their positions than they were the priorities of the population.”

Now Phillips is taking on 81-year-old President Biden for the Democratic nomination — and making the same argument he made about Feinstein and Pelosi. His longshot run has included several trips to California to appear on shows like Real Time with Bill Maher and court potential donors in Hollywood and Silicon Valley.

Nearly 80% of voters in a September Reuters-Ipsos poll said that Biden is too old to run again. More than half said the same about the 77-year-old Donald Trump.

Dean Phillips steps off his campaign bus at the New Hampshire State House. He filed a declaration of candidacy Oct. 27, 2023, to run in the state’s presidential primary.

(Glen Stubbe / Star Tribune)

Elected Democrats who refused to criticize Feinstein’s fitness to serve — or acknowledge publicly that Biden’s age is a challenge — are no better than Republicans who are unwilling to publicly criticize former President Trump, Phillips argued.

“It is the same disease — the same danger and the same consequence, which is the reduction in faith and government,” he said, noting that Biden is far better than Trump as a leader.

Phillips, who has voted with Biden 100% of the time in the House, has said repeatedly that he’s not in this race to tear down the president. He praised the Inflation Reduction Act, the bipartisan infrastructure bill and Biden’s “extraordinary” support for Israel.

But in his interview with The Times, Phillips was quick to say that Biden didn’t do enough to respond as vice president to Russia’s invasion of Crimea and that the Israel-Hamas war “could have been prevented with more extraordinary intentional peace efforts over the course of his tenure, both as vice president and now president.” He supports an internationally monitored cease-fire once all the hostages held by Hamas militants in the Gaza Strip have been released and says a multinational peacekeeping force should be deployed to the region.

He also attacked Biden’s unwillingness to legalize cannabis and the president’s response to “chaos” at the border.

Phillips sees what he’s doing as a “hopeful run” meant to offer a respectful alternative to someone whom he considers a successful president. He believes that by May or June, after enough campaigning, head-to-head polls will show him beating former President Trump and will continue to show Biden losing.

But his attacks on Biden over policy issues, and his recent claim that Biden — like Trump — is a threat to democracy have some political observers questioning whether he plans to run a purely positive campaign. They worry he could end up hurting Biden’s chances in a general election.

Phillips’ effort recalls former Gov. Jerry Brown’s runs for president, where he got in late and never accumulated enough movement support, said Danielle Cendejas, who works for the Strategy Group, a national political consulting firm that advised Phillips’ congressional bids but is not working on his presidential campaign.

“Phillips’ run feels like it’s more of a, ‘Hey, I’m an option’ campaign rather than, ‘I am trying to do something different because the president is not doing what I think should be done,’” she said. “Anytime you run against the White House, you are running on the fact that the president is just not doing a good enough job.”

If Phillips was running far to Biden’s left, his challenge might galvanize the White House to respond more aggressively, Cendejas says. But so far, the Biden team doesn’t seem too worried. (A spokesperson for Biden’s campaign declined to comment for this article.)

Phillips’ campaign counts Andrew Yang’s former campaign manager Zach Graumann as a senior advisor. Strategist Bradley Tusk, who managed Yang’s 2021 New York mayoral campaign and worked for Mayor Michael Bloomberg, said he was surprised that no nationally elected officials or activists had challenged Biden from the left.

The risk for Biden is he “could really underperform in the primaries but not lose them,” Tusk said. “Then Trump picks up a lot more momentum, raises a lot more money and fundraising for Biden gets that much harder.”

The two most urgent challenges Phillips faces are raising enough money to run a competitive campaign and getting on the ballot in as many states as possible. He already won’t be on the ballot in Nevada. He’s angry that he will likely be left off the ballot in Florida.

The Minnesotan, who thinks he’ll make the ballot in 90% of states, will appear on California’s ballot for its March 5 primary, according to California Secretary of State Shirley Weber.

Phillips and his team believe that a competitive primary is a healthy part of the democratic process. If the polls in May or June show Biden beating Trump “and me losing, I’ll be the first to acknowledge it and wrap it up,” he said.

Snuffing out dissenting voices only hurts the voters, argued Jeff Weaver, a senior advisor to Phillips who had top roles in Sen. Bernie Sanders’ 2016 and 2020 presidential campaigns.

Weaver thinks a strong showing for Phillips in New Hampshire, where Biden is not on the ballot but his supporters are marshaling a write-in campaign, will create momentum that will get him noticed by more voters. A poll last month in the state found Phillips with 15% support after two weeks of campaigning. Biden had 27% support.

“Our primary system is one of the only feedback loops between people on the ground and the national party,” Weaver told The Times.

“Issues and candidates affect how people vote. There should be a vigorous primary where people get to see their candidates talk about the issues. With there being no debates, the [Democratic] party has worked to stifle that process.”

President Joe Biden arrives at Santa Monica Airport in Santa Monica, Calif., Friday, Dec. 8, 2023. Rep. Ted Lieu, D-Calif., third from left, and California Gov. Gavin Newsom, left, and Los Angeles Mayor Karen Bass, right, look on.

(Manuel Balce Ceneta / Associated Press)

Phillips faces a steep financial challenge. In one weekend this month, Biden brought in about $15 million at two fundraisers in Los Angeles. Phillips said he will have trouble raising that kind of money—even as the Minnesotan who got rich running his family’s liquor business and later the Talenti gelato brand, has poured $2 million of own wealth into the campaign.

But Phillips has found some pockets of support.

Uber Chief Executive Dara Khosrowshahi, a college friend of Phillips, has supported his congressional races. Phillips said he has met in recent months with Open AI CEO Sam Altman — a meeting first reported by the news outlet Puck. Phillips told The Times he wasn’t sure if Altman, who gave $200,000 to the Biden reelection bid, had donated to his campaign.

He declined to detail how Altman, whose representatives didn’t respond to requests for comment, had been advising his launch except to say “I found him to be an extraordinarily brilliant and principled and magnificent ideator and convener and community builder, and without getting too much into the details, yes, he’s been supportive.”

Cryptocurrency billionaire Mike Novogratz has shifted his support away from Biden and will host a Phillips fundraiser, CNBC reported this week.

Phillips has held several Southern California fundraisers since launching his campaign at the beginning of November, though his campaign has declined to say how much they’ve raised. Phillips said the events attracted many Biden backers who pined for an alternative.

One was television executive Adam Goodman, who previously served as president of Paramount Pictures’ Motion Picture Group and DreamWorks SKG, and described how his high-school-age daughter heard Phillips speak and felt a connection to him. He’s been impressed by many of Biden’s successes over the last four years but still hosted a 100-person fundraiser for Phillips in his home early last month.

“This is the time when we’re supposed to be listening and auditioning the best people for the job and then ultimately we will get to a convention and the best candidate will go forward at that point,” he said.

Goodman said that politics — like show business — needs fresh perspectives in leadership.

“Show business is really in jeopardy right now,” he said. “The people who are actually really running the businesses who are at the top top top — these are people that have been in authority for 35-plus years. They are not people who necessarily understand the generational shift.”