Philadelphia Mayor Kenney at the June 2020 press conference where he first professed regret over authorizing the use of tear gas on protesters

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As the season’s first snow started to fall, Mayor Jim Kenney looked back on a year he’s long been wanting to end.

“I have a lot of regrets,” Kenney said in a phone interview.

In the distant galaxy of this time last year, Philadelphians were gathering for celebrations. They hugged loved ones without thinking twice. Tens of thousands sitting around family dinner tables still had jobs. The 2,200 residents taken by the coronavirus were still around, as were the nearly 500 lost to homicides. No one had yet been tear-gassed by police during one of the largest civil uprisings in the city’s history.

Going into 2020, Kenney faced some daunting challenges — gun violence, poverty, a potential recession. But the city’s financial health looked strong, and the administration was crafting a second term agenda it hoped would put a dent in these woes. His choice for new police commissioner, Danielle Outlaw, was supposed to pull the department into a new era of reform. The majority of the city, at least on paper, believed in him.

A year later, Kenney’s leadership is under question from critics on all sides.

Philadelphia’s response to the coronavirus is one target, drawing ire from some in the crippled business sector. But the city’s handling of Black Lives Matter protests over the summer — followed by the police killing of Walter Wallace Jr. this fall — is a major source of tarnished trust.

The loss of confidence is acknowledged by many of the mayor’s supporters, including members of his administration, who spoke on condition of anonymity to describe the internal quarrels. Some considered quitting the administration after the events of last summer.

“They don’t care,” one city official told Billy Penn about the administration. “I think you’re going to see a lot more people leave.”

For months on end, the 62-year-old son of South Philly was putting out fires at every turn. He saw his former managing director, Brian Abernathy, resign amid criticism over his handling of the summer events. Kenney was spotted dining indoors at a Maryland restaurant after banning indoor dining in Philadelphia. Thieves stole tech from the warehouse storing new voting machines ahead of a landmark election.

The blowback is not unique to Kenney. Democratic mayors in peer cities, from Mayor Lori Lightfoot in Chicago to Mayor Bill de Blasio in New York, drew harsh rebuke for their governance this year. And as in other cities, Philly’s other social ills only grew worse. Homicides skyrocketed to a level unseen since 1990. The School District of Philadelphia’s turmoil was compounded by remote learning. Major investments in education and infrastructure were sidelined.

In general, 2020 was a rough year to be running a U.S. city. It’s not about to get easier, because, as Kenney put it, “we’ve got no money.”

But the notoriously surly elected official says he’s optimistic about 2021, and hopes his revised second term vision can repair some of the distrust wrought this year.

“I’m very hopeful,” Kenney said. “You’re going to start to see things loosening up again, businesses opening up, and most importantly, kids going back to school.”

Philadelphia Mayor Jim Kenney in June 2020 Credit: Kimberly Paynter / WHYY

‘We thought we were the good guys’

The administration did move quickly to adapt to the unprecedented challenges presented by the coronavirus. Despite less help from the federal government than hoped for, Kenney’s team launched economic relief funds for small businesses, set up food distribution programs, and even fundraised from outside sources to provide assistance to those helping vulnerable residents.

One senior official said that, despite some missteps, the administration largely felt the pandemic response would be enough to maintain trust.

The first week of June changed all of that.

Government workers were among the thousands spurred to protest the killing of George Floyd in Minneapolis during the last weekend of May. Some were even among those tear-gassed by Philly police on the Vine Street Expressway, a fact that made its way up to the mayor’s office in the following days, sources said.

As the protests over systemic racism and police brutality continued into early June, debates raged within City Hall.

The tear-gassing of 52nd Street. Police shielding white vigilantes in Fishtown and South Philly. Mass arrests of protesters, and some reporters. Holding arrestees in the dilapidated, decommissioned House of Corrections.

Most people in Kenney’s circle — including the mayor — described those two weeks as their most difficult of their time in government.

“We thought we were the good guys, and in 30 seconds, we’re the problem,” said one official who considered leaving the administration at the time. Kenney said he personally reached out to those on his team who were impacted by the events and sought their advice.

The mayor and police commissioner finally took action after a damning New York Times video that repeated what local media had reported on several times about the Vine Street Expressway incident. A police commander was demoted. Kenney and Outlaw placed a moratorium on the use of tear gas.

“It’s one of the biggest regrets of my administration,” Kenney said of authorizing tear gas in the first place. “I’ll regret that for the rest of my life.”

The timing of the response fueled a sentiment that only the Kenney administration was responding to national embarrassment — not the criticisms of his own constituents.

“It was the opposite of anything I would have wanted from the Kenney administration,” Rabbi Ari Lev Fornari, of the Kol Tzedek synagogue in West Philly, said the actions in those weeks.

Police line up protesters after tear gas was used on I-676 in Philadelphia on June 1 Credit: Emma Lee / WHYY

Reckoning with leadership as the city roils

One of Philadelphia government’s major wins in this mess of a year was pulling off a historic election under international scrutiny. The November general became a collaborative effort involving thousands of public servants across various branches of government: the city attorneys fighting off the Trump campaign in court, the election officials who received death threats; the city staffers and temp workers who counted ballots around the clock.

But as fans of democracy cheered Philadelphia from around the globe, Kenney was not the face of the success.

Some feel Kenney could have performed better in the public eye this year. The mayor’s reluctance for the showy part of the job is no secret. A former councilmember, he prefers the behind-the-scenes bureaucratic work.

Asked about Kenney’s leadership style this year, Councilmember Allan Domb, a long-rumored candidate for the mayor’s office in 2023, recalled former Mayor Michael Nutter’s response to the fatal 2015 derailment of an Amtrak train in Port Richmond.

“What I remember most vividly was Mayor Nutter on TV at 11 o’clock at night, controlling the situation,” Domb said. “I think we as a city need to be out front in that leadership.”

Others defended Kenney, noting that few city leaders escaped this year with public trust fully intact.

“No big city mayor got it right in 2020,” said Councilmember Cherelle Parker, another rumored mayoral candidate who represents parts of northwest and lower northeast Philly. “I’m not here to second guess the mayor’s decision making over the last year. There was no manual or playbook for the multiple crises that he faced.”

Speaking privately, members of the administration said the mayor could have helped himself a lot by being more positive at times.

“Some people take it the wrong way when they don’t know his personality,” one official said. “He has to just brighten up a little bit.”

Some of Kenney’s personal decisions didn’t help his cause. Skipping town for a day trip in late August, Kenney and his fiancé made a reservation outdoors at a restaurant owned by a tailgating buddy in Chesapeake City, Maryland. The waterfront patio had been overbooked, and when the couple arrived, only indoor seats remained. The coronavirus case numbers were quite low in that part of Maryland, he reasoned.

“We just drove an hour and a half down, I’m not leaving,” Kenney said. “I take my mask off to eat…someone takes a picture… It goes everywhere on social media, and I’m a bad guy.”

Credit: Michaela Winberg / Billy Penn

A new year of austerity…and optimism?

In September, Team Kenney released its revised second term agenda — a plan called “Philadelphia Forward.”

The detailed proposal shows a path to economic recovery, and includes some of his earlier ambitions, like rolling out the Octavius Catto Scholarship, a free tuition plan for students to attend the Community College of Philadelphia.

Much of the agenda remains contingent on the city’s financial wellness.

Bracing for what would become a $750 million funding gap, the administration in April began slashing anticipated programs like universal street sweeping. Municipal unions were given one-year extensions rather than fully renegotiated contracts. The financial crunch isn’t over.

“We didn’t need to talk about brownouts, or closing firehouses or rec centers, but there were some pretty depressing conversations with the finance department,” Jim Engler, Kenney’s chief of staff, said of the budget discussions so far this year.

Engler reported to City Council that Philly’s fund balance has dwindled from $438 million before the pandemic to just $23 million this month. The revenue projections for the next fiscal year have many government officials hedging their hopes.

“The one thing about being semi-broke is that you don’t have a lot of options,” Kenney said. “Some people are going to be unhappy … and some people are going to understand. But the bottom line is, you can’t change it.”

His administration’s dealings with the police department will remain under heavy watch, with funding and a new contract key issues. So will the city’s murder count, which, as in other cities, spiked during the pandemic.

But Kenney is optimistic.

His new plan seeks a 25% reduction in homicides through a targeted operation next year. And as the vaccine disseminates throughout Philly in the coming months, he envisions a renaissance: more businesses re-opening, tourists and conventions making a return.

Pending public feedback, he wants to take some cultural trends of 2020 — like expanded outdoor dining and pedestrian-only streets — and make them permanent year-round.

Said the mayor: “I’m very hopeful.”

Max Marin (he/him) was Billy Penn's investigative reporter from 2018 to 2021. A graduate of Temple University, he has produced award-winning journalism on local politics, criminal justice, immigration...