PORTSMOUTH, New Hampshire—Dean Phillips’ coffee pot was running dangerously full.
On Sunday, the Minnesota congressman turned longshot primary challenger to President Joe Biden put in a mock shift waiting tables at a diner in a traffic circle—the aptly named “Roundabout Diner”—eager to connect with New Hampshire primary voters.
After being met mostly by bewildered out-of-staters in his laps around the diner, Phillips finally found the exact type of voter an attuned retail politician craves to corner.
“My story is, I’ve been waiting on an open heart surgery,” said Cathy Crawley, a retiree from Madbury, New Hampshire, who worked in the insurance industry.
As Phillips listened intently, coffee pot in hand, Crawley explained her exasperation at the U.S. health care system, especially after a career of trying to help consumers navigate the insurance landscape without getting fleeced.
After assuring Crawley that health care is “a big one for me,” Phillips explained he was a Democrat taking on the establishment to save the country from another Donald Trump presidency—and to create a “national plan” for health care so Americans like her wouldn’t have to go bankrupt to receive lifesaving care.
The multimillionaire liquor company heir didn’t elaborate much further on the key issue at hand. Health care, after all, hasn’t been a staple issue of his campaign—at least until now. He simply took his coffee pot and moved on to another booth.
“Definitely worth a Google,” Sarah LeVine, a 23-year-old voter sitting next to Phillips during the exchange, told The Daily Beast afterwards.
For Phillips, the more he tries to introduce himself to voters, the less he seems to know who he is in this presidential race.
About five weeks after kicking off his campaign, Phillips is grasping for a campaign rationale that extends beyond the fact that Biden is very old, relatively unpopular, and could lose to Trump. In the early days, Phillips was eager to note the president’s record on the U.S.-Mexico border and crime, sounding not unlike a conservative Democrat.
But in recent weeks, Phillips has started to sound like a “pro-worker” populist eager to outflank Biden on issues like marijuana legalization. Phrases like a “national plan” on health care convey a Rooseveltian sweep, but can leave more questions than answers in a New Hampshire diner booth.
The staff makeup of the Phillips operation has begun to reflect the identity crisis behind this Quixotic bid as well. At first, the congressman brought in Steve Schmidt, the combative longtime right-hand man to the late John McCain—and the co-founder of the anti-Trump Lincoln Project—as his senior adviser.
But as Phillips walked into a brewery in the town of Portsmouth after his diner stop, Schmidt was gone, with the candidate acknowledging the anti-Trump Republican had left the campaign.
Present instead were two new aides with far different pedigrees: Zach Graumann, the campaign manager of Andrew Yang’s 2020 presidential bid, and Jeff Weaver, Bernie Sanders’ 2016 campaign manager and an adviser for his 2020 run.
Schmidt is reportedly heading to a yet-to-be-named super PAC to support Phillips with unlimited outside money, according to The Washington Post. Helming the campaign itself are two operatives behind the most progressive campaign ideas of 2020, from Yang’s universal basic income proposal to Sanders’ Green New Deal and Medicare For All calls.
In New Hampshire, Phillips seemed to dismiss any concern over the messy politics behind his bid, framing it instead explicitly as a campaign “against the Democratic Party” and insisting he would take a “team of rivals” approach to his White House.
But through his evolving approaches, Phillips is proving in real time that a challenge to Biden predicated entirely on age, popularity, and a Democratic fear of losing to Trump can’t power a viable campaign through the early state gauntlet.
And for all of Phillips’ triangulation, for all of his self-reinvention, he may also be proving that Biden, for all his weaknesses, has not left much space to his left or right—at least, not space that Phillips is positioned to exploit.
An affable backbencher who has voted in lock step with Biden’s agenda, Phillips was always an unlikely primary challenger. The fact that he kicked his campaign off so late, and bet it all on a state that offers no delegates but plenty of prestige, led longtime allies like Minnesota Democratic-Farmer-Labor Party Chairman Ken Martin to dub it a “midlife crisis” campaign.
Now, that campaign itself may be having a midlife crisis.
With seven weeks to go until New Hampshire’s unsanctioned primary contest—and with polls showing him gaining little traction there or anywhere else—Phillips is running out of time to solve his existential conundrum.
A major obstacle is that, while Biden may not be popular on paper with Democrats—with roughly two-thirds saying they’d prefer someone else as the nominee in 2024—many of his policies are. So too is the legislative capstone of Biden’s former boss, the Affordable Care Act, whose “Obamacare” nickname Democrats went from avoiding to reappropriating in less than a decade.
Yet Phillips has recently picked health care as his main perch from which to stand out, and were LeVine from the corner booth at the Roundabout Diner to do her Google search on Phillips, she wouldn’t find a whole lot about his plan.
On the Phillips campaign website, there has yet to emerge a fully fledged health care plan beyond 185 words on the candidate’s promise to “support immediate action that gets us closer” to universal health care. (In Congress, Phillips has co-sponsored bills to expand Social Security and Medicare benefits to lower costs for prescription drugs and orthotics.)
Instead, young voters like LeVine would find stories Phillips had to deal with in past campaigns about his business practices not lining up with his purported progressive values—from denying health insurance from employees making $15 an hour to saying health care is a “moral right,” but “would necessitate a reduction in wages” for his employees.
When asked about his evolution on health care from his business days to the lofty rhetoric of his campaign holding up the possibility of universal coverage, Phillips said he was open to changing his mind.
“Frankly, my migration is based on keeping my heart and mind open, my ears open and listening,” the candidate told The Daily Beast. “And what I'm hearing too often is people just like this morning, she works in the insurance world and she needs heart surgery and she can't get it done because of the system.”
Phillips didn’t get into specifics on his plan beyond private insurance still existing in some capacity, describing “every single payer system in the world” as “a multi-payer system for the most part.”
And if the insurance industry, one of the most powerful in his home state of Minnesota—where he’s not running for re-election—would be furious as a result, potentially losing their jobs?
“Oh, they’re gonna hate me,” Phillips said. “And that’s fine.”
As for the voters, they still need a little more information. At the Roundabout Diner, after Phillips moved to the next table, Crawley had another question for the candidate.
“Dean,” she asked, “what’s your last name again?”