In the wake of Philadelphia’s recent primary, the focus has primarily been on the stunning victories of Democrats Larry Krasner and Rebecca Rhynhart, who swept their respective elections for district attorney and controller in a progressive wave that overwhelmed the city’s ward structure

But for many of the candidates in the Democratic primary for district attorney, last Tuesday became a day of reckoning. 

Former Managing Director Richard Negrín, talked up as an early frontrunner, lagged in fundraising and ultimately garnered strong support in just a few wards; much the same could be said for lawyer Tariq El-Shabazz. Former judge Teresa Carr Deni and former Assistant District Attorney Jack O’Neill only registered single-digit totals. But the sting of defeat was likely felt most strongly by Michael Untermeyer, a lawyer-turned-real estate investor. 

He spent $1.25 million of his own money on the race and walked away with just 8 percent of the vote – or about $100 spent for each of the 12,500 votes cast in his favor. So with arguably better name recognition, a one-month head start and nearly the same campaign war chest, why he didn’t fare nearly as well as Krasner, who was bolstered by $1.45 million from a PAC funded by billionaire George Soros late in the race?

Untermeyer told City&State PA he thinks his early money wound up putting a bullseye on him and his campaign.

"Ultimately, I believe investing in my campaign made me a target for my competitors, which occurs a lot when people fund their own campaigns,” Untermeyer said. “Larry and I never attacked each other and he ran a very classy campaign. You saw the results of that in Tuesday's outcome.”

Indeed, Untermeyer was repeatedly targeted by ads from former US Attorney Joe Khan, who would ultimately finish second in the primary. But political consultants interviewed for this article – who, it’s worth noting, all also worked on failed campaigns for other candidates in the race – were happy to offer their own opinions about what went wrong.

“Sometimes no amount of money can make a difference if you have a fatal flaw. See Tom Knox and Tony Williams,” said Khan media consultant Ken Snyder. Knox, a millionaire businessman, had dabbled in payday lending before making a self-funded run for Philadelphia mayor in 2007. Williams, a state senator, was backed by group of controversial, charter school-loving millionaires from the Main Line in his own failed 2015 mayoral bid.

Snyder compared these traits to Untermeyer’s history as a Republican-turned-Democrat. The party switch – he registered as a Republican to challenge then-candidate Seth Williams in 2009 – effectively killed his chances in a race where all candidates ran on a similarly progressive platforms, he said.

“Knox the payday lender was never going to get past that. Williams the private school voucher guy was never going to get past that. Untermeyer the Republican was never going to get past that flaw either – and he didn’t,” Snyder explained.

Indeed, internal polling numbers from the Untermeyer campaign reportedly showed a majority of Philadelphia voters – some 80 percent of whom are registered Democrats – did hold the party switch against him.

Mark Nevins, a consultant who worked on Negrín’s campaign, said the pacing of Untermeyer’s ads was also problematic. Although the candidate had run other campaigns before, including for sheriff and City Council, his DA campaign this time around wanted to come out early on television in an effort to build name recognition. That’s not to mention intimidating less-well-funded opponents and attracting ward support with the lure of cold, hard cash.

Nevins thinks the slow drip of commercials instead blunted the impact of the ads, compared to a media blitz late in the race when many voters were deciding whom to back.

“It’s the difference between trying to put out a fire with a hundred squirt guns instead of one fire hose,” he said. “You could tell from the polls it just wasn’t moving numbers for him.”

But Neil Oxman, the storied consultant behind the Campaign Group, said that’s simply not true. He handled Untermeyer’s media efforts (along with Rhynhart’s wildly successful campaign for controller) and said internal polls showed his strategy was working – for a time.

“We thought since everyone was in single digits and this...was the cycle with the fewest big races and the one where the ward leaders would exert the most control,” he said. “We moved from single digits to double digits – and then the Khan campaign attacked us. If we knew it was not going to be a ward leader election, we would have done things differently.”

Snyder acknowledged that the repeated attack ads were deliberately intended to stave off Untermeyer’s early rise at a time when other candidates, including Khan, were still largely unknown to the general public. 

It worked, and many have since praised Khan’s robust fundraising and second-place showing. But one of the biggest questions being posed by political observers in the aftermath of Khan’s air war is why he didn’t pivot to target Krasner as his outside support surged.

“If we had abandoned the attack on Untermeyer and shifted to Krasner, we risked letting Untermeyer continue to grow without any guarantee that an attack on Krasner would result in votes going to Joe,” Snyder said. “Frankly, we weren’t sure that there was an attack on Krasner worth running. Joe and Larry agreed on almost everything. The fact that Krasner never prosecuted a single case in his career was really the only way we could go and it’s not even clear that it was a good hit. We switched to all positive...and hoped that either the press would scrutinize Krasner more deeply or another candidate would go after him.”

Oxman says today that the strong, unexpected progressive voter turnout for Krasner, which some have credited as a reaction to Donald Trump’s 2016 presidential election victory, meant victory was never really in reach – especially with Untermeyer’s elephantine Achilles heel.

“The answer is that even if no one had attacked us, we would have probably still ended up with 15 to 20 percent of the vote” – Krasner finished with 38 percent, while Untermeyer got 8 percent and Khan tallied 20 percent – “So, we maybe could have ended up with what Negrín got.”

(Nevins, for his part, reflected on Negrín’s own lukewarm performance thusly: “We could have raised another $500,000 to be on TV longer and stronger. It could have been a three- or four-candidate field instead of eight. George Soros could have minded his own business...It’s never just one thing.”)

Untermeyer has now sunk over $1.5 million of his own money into fruitless bids for office over the past eight years. Sources say that besides endorsing Krasner and lobbying for a white-collar crime unit he promoted on the trail, his political days are probably over. 

The businessman says he held no grudges or illusions about the race. He says he knew what he was getting into from the beginning.

“I am 66 years old and I have had a long and successful career as a prosecutor and investor. I chose to step up and decided to run because I genuinely cared and believed this office needed reform and new ideas,” he said. “That's why I put my money, heart and time into this campaign.”

This article has been updated to change the photo accompanying it. The original photo was taken by the Philadelphia Inquirer's David Maialetti and was used inadvertantly.