From his campaign headquarters on West Third Street in Chester, Stefan Roots put it plainly: he was fed up with the way things were going. Streets were blanketed with litter, people were moving out and the city was on the brink of financial ruin. Someone had to do something. 

As the bass from a car’s subwoofer reverberated somewhere outside, Roots smiled, saying he was lucky to have a brick and mortar office at all — that no candidate for mayor in the last twelve years had ever had one. The truth was, he said, no one ever needed one.

Born and raised in Chester, Roots, 62, was adopted as a baby when he was born to a fifteen-year old single mother and almost literally “dropped on a doorstep.” He’s worked as an engineer for Philadelphia Gas Works, a manager at IBM, a substitute teacher and a blogger. Now, he is just a few months away from being elected the city’s next mayor.

“For us to locate right in one of the worst neighborhoods in terms of services and housing and retail made a big difference for a lot of people,” he said. “It’s almost like one brick is falling down a day. Over time, you kind of don’t even see the mass decay.”

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Chester, the oldest city in Pennsylvania, is suffering from an economic crisis so serious its officials have been warned it could soon be unincorporated as a city. But political winds of change are coming to Chester. Last month, Roots, a freshman city councilman, defeated two-term incumbent Mayor Thaddeus Kirkland in the Democratic primary by a 3–1 margin. His surprising upset ended Kirkland’s long winning streak in the beleaguered city of Chester. Prior to his rise to power as mayor, Kirkland represented Delaware County in the state House for more than two decades. 

Now, with no Republican on the ballot in November, Roots is virtually guaranteed the mayorship. He will soon be charged with helping a court-appointed receiver navigate the city out of bankruptcy and onto a path of financial independence. His success or failure may be a litmus test to determine whether Chester can sustain itself long-term.

The city is currently facing a $45 million deficit — with most of the debt owed to police pensions. In February, Commonwealth Court Judge Ellen Ceisler delivered a 45-page ruling in Chester’s bankruptcy case, writing that the city was “dysfunctional” and plagued by nepotism and incompetence. For the past two years, the receiver has locked horns with the current administration, citing examples of obstruction, unethical behavior and even threats. 

Roots said part of the problem stems from Kirkland ignoring the elephant in the room. 

“I often say that I can balance my checkbook, too, if I don’t pay my electric bill,” said Roots. “So, there were some things that just weren’t brought forward to give people a hint that we were quickly deteriorating financially.”

Roots doesn’t consider himself a politician or even a journalist. He first started getting noticed in the community about 10 years ago when he penned the piece “Chester is trashy” on his blog, in which he lamented the blight around the city. He soon developed an audience online and got the attention of Todd Strine, publisher of the community newspaper the Swarthmorean, who encouraged him to get into politics. Apprehensive at first, Roots said he was eventually persuaded to run for City Council in 2021 — and won a seat decisively. That set him on the path to run for mayor the following year. 

But he faced an upward battle knowing voter turnout in Chester was historically low and the city’s Democratic Party leadership had backed the incumbent for decades. This resulted in a general feeling of malaise among the public.

“If they were supportive of Kirkland and his regime, they came out and voted. If they weren’t, they didn’t have a choice. So, the choice for many was just to stay home,” he said. 

I had to put the message out to people that this could be the last mayoral election in the city of Chester. So, choose wisely.

Kirkland disputes claims that he has done little to engage voters over the years. He said he regularly held voter registration events and is not at fault for the city’s pension problem. Instead, he said he inherited it. Asked why he thinks he lost the Democratic nomination, Kirkland blamed it on “a barrage of lies.”

But Roots credits his win with his willingness to challenge the party’s inner circle, which was “virtually unthinkable,” he said. With the help of Strine and a small group of supporters early on, Roots said he put together a smart campaign with strategic planning, door-to-door canvassing, writing letters to the editor and trying to distinguish himself from Kirkland. This made him an insurgent Democrat. 

“The average person in Chester doesn’t vote because everybody who they’ve ever known — for generations now — has felt left behind by the political process,” said Strine. “Our basic theory was that if we get leadership in the city that people can trust, then we can start to turn the city around in a way that’s going to benefit the folks who live there.”

After Election Day, Roots walked away with more than 61 percent of the vote, besting Kirkland and real estate broker Pat Worrell. Some pointed to Kirkland’s thorny relationship with the state-appointed receiver as a major sticking point in the race.

“He is very sure of himself that his style of leadership, the government that he has in place, and Chester in general, is doing fine — even though everything around him has changed with regard to receivership and bankruptcy and just basic services not being delivered. He still believed that the course he was taking was the right one,” said Roots.

“[Kirkland] had a “stranglehold” on Chester politics for so long, it became sort of a machine type of government where, as the head of the party — the top elected official from the city — he called virtually all the shots with regard to who got to participate in city government, as both elected officials and employees.”

Roots is optimistic that his administration will bring with it access to new economic opportunities the city hasn’t seen in years.

Chester has several valuable assets — Subaru Park, home of the Philadelphia Union, and Harrah’s Casino, among others. But Roots has been critical of one of Chester’s biggest economic drivers — the controversial Covanta trash incinerator on the waterfront. The facility — which receives hauls from as far north as New York City and as far south as Ocean City, Maryland — burns roughly 3,500 tons of trash a day and converts it to energy. It has garnered criticism from neighborhood activists who accuse Covanta of environmental racism and unfairly burdening low-income communities. 

Covanta's Delaware Valley Resource Recovery Facility in Chester.
Covanta’s Delaware Valley Resource Recovery Facility in Chester.

Roots said he wants to see new industries built up, including IT training for youth that pays a living wage. 

“We don’t want to be dependent on Covanta any longer to keep this city afloat financially,” he said. “It is virtually impossible to put market rate housing on Chester’s waterfront next to an incinerator.” 

When Roots takes office in January, he said he will work with the receiver to help lead the city out of bankruptcy and onto sound financial footing. Part of his platform running for mayor included the concept of compromise. If the receiver was removing incompetent elected officials — including the mayor and city council members — he would cooperate. Exactly how that looks in the future, however, is unclear. 

“I had to put the message out to people that this could be the last mayoral election in the city of Chester. So, choose wisely,” he quipped.

Donald Johnson, owner of 2701 Sports Bar & Grill in downtown Chester, is one voter who got that message. He said Roots stopped by his bar one day to introduce himself.

“I spoke to him for a few hours and he just made me believe that we could do something different,” Johnson said. “It was cool that he came here and showed his face. He didn’t have to and he did. That meant something to me.”

Chester’s general election is Nov. 7. For Roots, it’s going to mean another brand new start. 

Jenny DeHuff is an accomplished writer and editor, having been a part of the Philadelphia media landscape for nearly 20 years on just about every level of journalism. From covering cops and courts to authoring Philly’s hottest gossip column, she’s learned that what she likes to write about most is politics and navigating its murky waters each election cycle. Over the span of her career, she’s won multiple awards for investigative journalism.

One thought on “UpRooted: How establishment Democrats lost their stronghold in the city of Chester”

  1. Good luck Mr. Roots. Chester has a decades long culture of bad government and worse politics. I hope you get folks on City Council that will work with you and the receiver to change the course of Chester. Thank you for your vision and optimism. A great place to start.

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