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Through much of Mayor Cherelle L. Parker’s first two years in office, most political insiders in Philadelphia assumed she would cruise to reelection.

After all, no mayor in the last eight decades in the deep-blue city has lost a bid for a second term. And Parker is backed by the city’s long-powerful Democratic establishment, contributing to the foregone conclusion that their allied mayor would win again.

Even some of Parker’s staunchest critics on the left admitted privately that they were resigned to her serving eight years in office.

Then last month, conventional wisdom started to crack.

State Rep. Chris Rabb — a democratic socialist and an anti-establishment firebrand — won a tightly contested battle for an open seat in Congress, prevailing over Parker’s endorsed candidate and even carrying the 50th Ward in Northwest Philadelphia, where Parker is ward leader.

Now some of the activists who lead the city’s largest left-leaning organizations think that race showed that Philadelphians are ready to pick a progressive over the Democratic establishment. And they are looking at next year’s mayor’s race again, asking the question: Is Parker vulnerable?

“We would love to have a progressive challenger in this race,” said Sergio Cea, political director of the progressive group Reclaim Philadelphia. “The establishment was really defeated on all fronts this election cycle.”

In a little more than 10 months, Parker, a centrist Democrat and the city’s first female mayor, will be up for reelection. She has not officially announced a campaign — doing so would trigger strict fundraising rules and limits — but all signs indicate she intends to run again, including an already huge campaign war chest.

Any challenger to Parker would be considered a significant underdog. The mayor has the power of incumbency, and can point to progress on her 2023 campaign promises to make the city safer and cleaner, not the least of which is a historically low homicide rate. Thousands of residents are getting their trash picked up twice a week, and polls consistently show that more Philadelphians say they think that the city is heading in the right direction now than when Parker took office.

She even seemed to recover politically after one of her lowest moments: the eight-day municipal worker strike last year that left so much garbage piling up that it became colloquially known as “the trash strike.” Parker, through her signature unyielding negotiating style, muscled her way to an agreement with the union.

Today, she is supported by most of the city’s elected officials and powerful organized labor groups. Ryan N. Boyer, the head of a coalition of deep-pocketed building trades unions, said recently that any challenger to Parker would face “annihilation.”

“This is Philadelphia, there are always people who want to run for mayor. But mayoral elections are decided on whether people think their city is moving in the right direction,” said Aren Platt, executive director of People for Parker, the mayor’s political campaign arm. “Mayor Parker has been underestimated her entire career, and she has a habit of proving people wrong.”

However, some on the left see a coalescence of forces that could bolster their chances: national frustration with the Democratic establishment that has manifested in leftist wins, a widespread anti-incumbent sentiment, and liberal rage toward President Donald Trump, whom Parker has largely avoided maligning publicly.

They also see potential signs of Parker’s power waning, including her recent budget battle during which she could not get Democrats in Harrisburg and City Hall on board with her tax plans.

“If you just have the right candidates that are able to speak to the dissatisfaction of Democratic voters in Philadelphia,” Cea said, “I do think [Parker] is in trouble.”

But the biggest question for Philadelphia progressives in the approaching mayoral race remains: Who could be their candidate?

The potential challengers

Jack Inacker, a Democratic strategist based in Philadelphia, said there are few, if any, challengers to Parker who could pull off a win in 2027.

“The progressive infrastructure now has built up in a way where, if you squint really hard, you can see a path to a progressive challenger,” Inacker said. “The problem is that [Parker] is one big mistake away from being beatable, but she’s not beatable yet. And people know that.”

Candidates have plenty of time to decide. Paperwork to get on the ballot likely would not be due until March.

Perhaps the most talked-about potential challenger so far is District Attorney Larry Krasner, the city’s most prominent progressive. He has not ruled out a run for mayor, and he has recently publicly criticized Parker and some of her closest allies.

Last week, he invited media to walk along with him while he hand-delivered a letter to the mayor’s suite in City Hall to express dissatisfaction with his office’s budget. Parker called the move “stunting.”

Platt, in a thinly veiled shot at Krasner, said in a statement that “what we’ve seen recently is too many politicians focused on generating headlines rather than solving problems: manufacturing controversy, looking for someone else to blame, and confusing political theater with leadership.”

Krasner has won citywide election three times, twice winning reelection in landslide fashion. He is one of the nation’s most well-known progressive prosecutors and one of the city’s most polarizing figures. His base of support includes the city’s left, as well as a large swath of Black voters and elected officials.

But it was Parker’s political family — the vaunted Northwest Coalition of the some of the city’s most storied Black politicians — that was key to Krasner’s political ascent. Challenging Parker could be seen as a betrayal by some in the voter-rich northwest corner of the city, and his base there could fracture.

Krasner has also in the past struggled to keep up with his opponents in fundraising. Any challenger to Parker would likely need to bring in well over a million dollars, a sum of money that Krasner has never raised before.

Several other elected officials are seen as potential challengers to Parker, including several sitting members of City Council.

Councilmember Isaiah Thomas, who represents the city at-large, has long been rumored to have ambitions for higher office. He has been elected citywide twice, and recently was among the most vocal opponents of the Philadelphia School District’s controversial plan to close 17 schools.

And he has allies both on the left and in the city’s business community, the latter of which has been frustrated with a Parker administration policy shift that increased the tax burden on small businesses.

Thomas said last week that he is focused on his job in City Council.

“That job right now is hard enough, looking at the affordability crisis, the crisis around public education, and other issues that we’re facing,” he said.

There’s also two-term Councilmember Jamie Gauthier, who represents parts of West Philadelphia and has positioned herself as one of Council’s chief critics of the Parker administration. She said earlier this year that running for mayor “could be interesting one day,” but that she would not run if she did not see a clear path to victory.

She said in a statement that her focus is “finishing what we started on City Council, especially building affordable housing.”

Gauthier added: “But it’s clear Philadelphians are hungry for leaders who will put working families above big business.”

And there is Councilmember Kendra Brooks, the de facto leader of the city’s left-leaning coalition and a member of the progressive Working Families Party. Brooks, who represents the city at-large, has twice campaigned and won citywide.

A political adviser to Brooks said she is focused on her work in City Hall and running for reelection to Council, as well as “building Black progressive political power through the WFP.”

What do progressive gains mean for the 2027 mayor’s race?

Parker’s camp sees strength in her numbers.

In March, the mayor’s political arm commissioned a poll that found that 60% of respondents approve of the job Parker is doing as mayor, while 33% disapprove. Her approval rating was even higher among Black voters, older voters, and residents of Northwest Philadelphia — one of the highest-turnout areas of the city.

Cornell Belcher, one of the top Democratic pollsters in the nation, has conducted polling for Parker dating back to her mayoral campaign. He said that a key indicator of voter attitude toward an incumbent mayor is the number of residents who think the city is heading in the right direction.

The results this spring, he noted, were “dramatically different” from when Parker was first campaigning for the office. In April 2023, Belcher measured that 66% of Democratic primary voters in the city were dissatisfied with the direction of Philadelphia.

Today, he said, 62% are satisfied.

Still, other polls have shown potential warning signs for Parker.

In three polls that were conducted this spring in the 3rd Congressional District and obtained by The Inquirer, an average of 48% of Democratic primary voters said they had a favorable view of Parker and 41% had an unfavorable view. The polls, which measured voter attitudes in roughly half the city, were conducted by three different firms, and they were commissioned by different campaigns and organizations.

Approval and favorability ratings are not apples-to-apples. An approval rating is often considered a more reliable data point for an incumbent executive, because it measures attitudes about job performance, not reputation.

Belcher, who founded his polling firm 25 years ago and polled for former President Barack Obama, said he would not draw conclusions from polls of a congressional district that includes only half the city and was taken in a different election year. And he questioned other pollsters’ methodology in Philadelphia, a city that is tricky to survey.

“A city like Philadelphia, with all its different racial and ethnic groups, getting that right is hard,” Belcher said. “The more diverse an area is, the more work you have to put into getting it right.”

The results of last month’s congressional race energized progressives, in part because Rabb performed well in parts of the city that Parker carried when she won the crowded open Democratic mayoral primary in 2023. An Inquirer analysis found that more than a quarter of Rabb’s votes came from divisions that voted for Parker in 2023.

Rabb won his Democratic primary in a race that included three front-runners. But mayoral reelection battles in Philadelphia have historically been head-to-head, meaning the winner will look to reach 50% of the vote, a more challenging proposition for an ideological candidate.

Platt said he would caution against concluding that Parker is politically vulnerable based on the outcome of the congressional race.

And he said Rabb’s win in Parker’s 50th Ward is not a sign of cracks in the mayor’s base. He noted that the ward’s Democratic committeepeople last week unanimously reelected Parker as ward leader.

“The mayor is organized, and her coalition across Philadelphia is strong,” Platt said. “They may not be active on Reddit, but they’re there, and they believe in what she’s doing because they can see the results in their neighborhoods.”