Public housing resident Sheila Armstrong knows she’ll need to do some serious fundraising for her campaign against Council President Darrell Clarke.

But as the single mother sets out to court donors, she’s run into a problem. People are terrified to give her money because of who she’s running against. Even the act of trying to raise money has built-in resistance, Armstrong discovered. Convincing a local venue to rent her space for a fundraiser was a struggle, she said, because the business owner worried about political retribution.

“When you run against an incumbent, no one wants to support you,” Armstrong said. “I had one elected legislator laugh in my face.”

Some potential donors fear backlash could hurt their business interests. District councilmembers hold a vice-grip on development in their neighborhoods under a contentious tradition better known as councilmanic prerogative.

“Councilmanic prerogative strikes fear into the hearts of a lot of people,” said candidate Lauren Vidas, who’s challenging District 2 Councilman Kenyatta Johnson in the May primary. “I have a conversation 10 times a day that’s like, ‘You’re great, I’d love to support you, but I can’t be on your campaign finance report.’”

Some argue the Tammany Hall perceptions of Philadelphia’s City Hall are exaggerated, but you won’t find a campaign veteran or political insider who’d deny the sentiment is powerfully present. It explains, at least partially, why so few challengers have jumped into district council races compared to the 27 contesting for the seven at-large seats.

“It’s problematic to give money to challenger when you have a strong incumbent,” said consultant Mustafa Rashed, “especially if you want to do business in the neighborhood.”

Rest assured the defending campaign is keeping tabs on its rival donors, he added.

It helps to be rich

Mark Nevins, a Democratic consultant who works for Johnson and also District 1 Councilman Mark Squilla, says the image of lawmakers enacting revenge on donors to their political rivals is overblown.

“I think it sounds a little paranoid,” Nevins said, while also acknowledging fear of retribution can be a considerable barrier. “Money in politics always makes people uncomfortable. The fact is, elections cost money to run.”

There’s no consensus on how much money you need to run a competitive district council race against an incumbent. Estimates range from $150,000 into the millions. It can all depend on how much money your challenger has, too — and what kind of campaign you want to run. Getting on television is prohibitively expensive in Philadelphia, which vacillates between the fourth and fifth priciest media market in the nation.

Vidas, who launched her campaign last summer, showed around $40,000 on her annual campaign finance report. Johnson, who has developed into Council’s most prodigious fundraiser, headed into election year with over $620,000 in the bank.

Money doesn’t guarantee victory. Just ask Tom Knox. If you’re thinking, “Who’s Tom Knox?” — well, case in point. His claim to fame was sinking nearly $11 million of his own money into the 2007 mayoral primary only to finish second behind Michael Nutter.

“The most successful district challengers are the ones who can self-fund,” said Rashed. “They aren’t reliant on individual donors.”

Money can turn a lackluster wannabe into an insurgent force — and can keep an inspiring candidate from ever getting their message across.

“Money is options,” said fundraiser Aubrey Montgomery. “Money is your ability to communicate. If you can’t do that, you can’t advocate for yourself and your ideas.”

‘Angering the sitting council person is not a good idea’

The calendar is another reason raising even $150,000 is a challenge for those running against powerful incumbents.

City campaign finance law favors incumbents by capping contributions per candidate per year. Individuals can give no more than $2,900 to a candidate annually, and the limit is $11,900 for a political action committees and businesses. If you launched your 2019 campaign last year, you only have two chances to receive a big check from your staunch supporters. Meanwhile, sitting councilmembers spend year after year courting donors to pad their war chests. Some fundraise defensively to ward off potential challengers.

“Clearly it doesn’t scare people off challenging him,” Nevins said of his cash-rich client Councilman Johnson, “because people still feel free to run for office.”

The really big money in City Council races comes from unions and developers. A PlanPhilly analysis found at least half of the $2.3 million donated to sitting members last year came from labor groups and the real estate industry.

Unions rarely throw big money behind district challengers, a situation that has frustrated Tonya Bah, the Democrat gunning for Councilwoman Cindy Bass’ seat in Northwest Philly.

“I have endorsements from powerful grassroots organizations but most labor unions are not going to put their necks out when there’s an incumbent in the race,” Bah said. “Angering the sitting council person is not a good idea.”

Observers like to point to exceptions to the rule about unseating incumbents. In 2017, City Controller Rebecca Rhynhart raised over $425,000 and won a citywide race against incumbent Alan Butkovitz, a Democratic party insider who is now running for mayor against Jim Kenney.

Usually, running against an incumbent requires not only a lot of money, but also a political weakness — like some kind of big scandal — or a divide among party leaders, as in the case of oft-challenged Councilwoman Maria Quiñones-Sánchez. That’s not the case for at-large seats.

“If you run for at-large no one holds it against you because they’re all open seats,” said consultant Rashed. “But if you’re running against a district councilman, you’re straight up challenging someone.”

Editor’s note: This article has been updated to correct the amount of money raised by Rebecca Rhynhart’s campaign in 2017.

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...