In recent history, no other potential presidential candidate has had a more humiliating run of press coverage before even announcing their decision to run than the New York City mayor, Bill de Blasio.

“Is Bill de Blasio trying to escape New York City by running for president?” asked New York-based Observer. “De Blasio PAC spends $30m on ads urging candidate not to embarrass self by running,” wrote the Onion, not entirely unbelievably. New York magazine aggregated a listicle of everyone who has told the mayor he shouldn’t run. Among them: old advisers, “self-described friends”, recent advisers, his own wife.

It’s hard to overemphasize the lack of enthusiasm De Blasio will be starting off with as he enters the race. In a Quinnipiac poll last month, 76% of New Yorkers agreed that their mayor should not run for president. This included 70% of black voters, who usually make up De Blasio’s strongest base of support. As the Washington Post’s Philip Bump pointed out, De Blasio was a standout in another poll, this time of national Democratic primary voters, for being the candidate with the highest unfavorability ratings. He was also the only candidate with net unfavorability, with more respondents having an unfavorable than favorable view of him. The Quinnipiac poll even showed that one-third of Democrats in De Blasio’s home city – what ought to be his main bulwark of support – disapprove of his job performance.

Yet in a Democratic primary that has already become, in many ways, a sprint towards the left, the level of contempt against a mayor who was once hailed as a progressive voice seems somewhat outsized. After all, as De Blasio’s most fervent supporters will point out (even if De Blasio is now chief among them), the mayor has had big progressive policy wins, ranging from supporting a $15 minimum wage to providing free lunch for public school students. And he has broken the city from a decade-plus of Michael Bloomberg’s pro-corporate disposition, despite constantly being hamstrung by the nemesis who presumably should have been on his side, New York’s governor, Andrew Cuomo. So how did De Blasio – who was elected to his post in two successive landslide elections after serving as the city’s public advocate – so thoroughly end up losing the love of the left?

As I recently reported in the New Republic, the reasons why the mayor’s presidential ambitions are seen so widely as a sad joke are varied, having as much to do with De Blasio’s personality and record as with the current state of the Democratic party.

Take the meatiest bit first: De Blasio’s policy record. It’s true that the mayor has had major, progressive wins over his tenure. What Democratic candidate can claim to have enrolled 70,000 children in universal pre-K? But the inequality De Blasio promised to eradicate during his campaign is still felt by the city’s residents in pressing ways. The clearest example is housing.

While the housing crisis has been decades in the making, both at the state and federal level, affordable housing continues to vanish and neighborhoods are rapidly gentrifying under his tenure. Even as the mayor credibly argues that he’s done more than his predecessors to address the issue, his halting attempts to counteract the effects – including “affordable units” in the luxury towers and complexes that are invading the cityscape – have been consolations at best.

Homelessness stubbornly increases year after year. One mismanagement scandal after another piles up at the New York City Housing Authority, the biggest public housing authority in the country. “Every year that I can remember, at least one NYCHA building doesn’t have gas during Thanksgiving,” Afua Attah-Mensah, executive director of Community Voices Heard, once told me.

Similar failures can be felt by everyday New Yorkers when it comes to policing practices that are thankfully less draconian but are still brutal to those who face disproportionate ticketing, arrests and violence. And despite well-meaning rhetoric and attempts at coalition-building, the city is still plagued by a highly segregated educational system, and decaying public transportation (Gothamist has the run-down, both good and bad).

All of these are crucial issues for any Democratic candidate, and ones that cannot be mitigated by De Blasio’s other, major wins. His mixed record in these areas has cost him support from the network of community groups that helped get him elected in the first place. And his typical incumbent’s penchant for industry investment, including his warm welcome of Amazon, has also turned off the newly empowered Sanders-AOC-DSA wing of the party. Suddenly, it’s hard to think of a big progressive group that vocally champions him.

But the historically tall mayor’s problems with the left cannot just be ascribed to his policy record. After all, he is no “closet moderate”, as some call Beto O’Rourke (and Pete Buttigieg is proudly running as policy-lite). When asked about Mr de Blasio’s unpopularity, a basic thing almost any political operative (and more than a few regular New Yorkers) will point out is his toxic relationship with the press. Famous for his outbursts towards conservative and liberal papers alike, the image that we get of De Blasio in return is one of all pants, and no poise. We remember the groundhogs he’s dropped, the SUV trips he’s taken to the Park Slope YMCA, and, more seriously, the employees that he berates and condescends to.

In a city with a tabloid-heavy press culture, it’s a problem that goes both ways –making the question not just whether the mayor has the record to sustain a presidential run, but also the temperament. Even if the New York press may constantly put De Blasio through the wringer – in a way that most other Democratic candidates have not yet faced – the mayor’s hapless inability to rise above the scrum to communicate his progressive causes shows a lack of sensibility that is necessary for a presidential candidate. Even those who claim that De Blasio has the right message sometimes admit, as his own former campaign adviser Rebecca Katz politely did, “I’m just not so sure he’s the right messenger.”

After more than five years in one of the top roles in America, running its biggest city, De Blasio has one bad political compromise and one negative press story too many fit the role of Democratic dream contender. Still, with New Yorkers practically begging for him to focus on problems at home, the mayor has a chance to repair the relationship with his own city. But there are perhaps only two words that are sure to ring the death knell of De Blasio’s reputation as New York’s progressive hero: he’s running.

• Clio Chang is a New York-based journalist