Two Republican contenders -- one Jewish and the other a non-Jew with Jewish interests -- are hoping to pull off the upset of a lifetime come Election Day on Nov. 3.
In a city where Democrats outnumber Republicans by a 7-1 margin, the last time a GOP candidate sought citywide office, he got 17 percent of the vote.
Most pundits have already consigned the GOP candidates to a similar fate.
In one race, Michael Untermeyer, a Jewish attorney, is facing Democrat Seth Williams to become the city's next district attorney. The winner will replace Lynne Abraham, who has held the post for 18 years.
In the race for city controller, Al Schmidt is hoping to unseat the incumbent, Alan Butkovitz. Schmidt worked for President Bill Clinton's Commission on Holocaust Assets in the United States and partly focused on Judaic studies while earning his Ph.D. at Brandeis University.
Butkovitz, a one-time state representative from Northeast Philadelphia who was elected to citywide office in 2005, will most likely become the city's top Jewish elected official with the retirement of Abraham.
Typically, turnout in Philadelphia in races for city controller and district attorney fall below 15 percent. And at least this year, these races have gotten little media play.
"It's going to be awfully hard for them to win," Jeff Jubilerer, a Philadelphia-based political analyst, said of the Republican candidates.
Nevertheless, Harold Yaffe, a major political donor who co-chaired Philadelphia Mayor Michael Nutter's finance committee but is now backing Untermeyer in this race, said that a low turnout gives the underdog a chance to pull off a surprise.
Schmidt's and Untermeyer's campaigns have gotten some favorable press in recent weeks, including an endorsement from Philadelphia Daily News columnist Stu Bykofsky.
Bykofsky wrote that voters should back the GOP candidates to break the Democratic "monopoly" on city government.
Checks and Balances?
Not surprisingly, Schmidt, a 38-year-old Pittsburgh native, agrees.
"Having a city controller from the minority party would be a great asset to the city. Who thinks one party rule is a good thing?" he said. "If you don't have it, what you do have is no checks and no balances."
Schmidt, who was raised in the Lutheran faith, said that he first became interested in Jewish history and philosophy while a student at Allegheny College. Later, at Brandeis, he researched the German occupation of Bavaria and the consequences for the local Jewish population during World War II.
Schmidt has fiercely criticized Butkovitz, charging that the incumbent hasn't closely audited city agencies run by Democratic ward leaders.
"The city controller depends on the people he audits. But independence is key to the whole thing," said Schmidt.
Butkovitz, however, paints a different picture. The controller -- who pushed for city divestment from Sudan, among other things -- said that he has tripled the number of performance audits of city agencies, which have resulted in more than $413 million in savings and potential revenues for the city.
Last month, he also began a program of deducting from the paychecks of city employees who owe back taxes.
"We have consistently infuriated people in our own party and the 'powers that be' in Philadelphia by very hard-edged audits," said Butkovitz, 57.
The reason that the Republicans can't win any election in Philadelphia, he added, "is that they do not appeal, across the board, to all the people of Philadelphia."
Untermeyer, 58, an Old City resident whose varied career has included stints in the State Attorney General's office and as assistant district attorney, actually switched from Democrat to Republican earlier this year. He said that the district attorney's office should be nonpartisan, and that he's running as a Republican to give himself a better chance.
Untermeyer's list of proposals include stricter penalties for gun offenses, reshuffling the deck so that one prosecutor handles a case from beginning to end; and using GPS and cellular phone technology to keep tabs on nonviolent offenders to reduce prison overcrowding and save the city money. (To demonstrate this, he wore an ankle bracelet for a month, allowing anyone who logged on to his Web site to track his whereabouts.)
He also hopes to set up a body where representatives of the city's ethnic and religious communities would meet regularly with the district attorney to discuss concerns.
"What's at stake is public safety in this city and the future of this city. If Philadelphia is a safe city, people will live here, they'll work here, they'll visit here," said Untermeyer. "Philadelphia has too much gun violence. What's my solution? It's to have a zero-tolerance party on illegal handguns."
Williams spent 11 years as a city prosecutor. He unsuccessfully challenged Abraham in 2005, but won a tough five-way Democratic primary in May.
If elected, the 42-year-old would be the city's first African-American to hold the office of district attorney.
Williams insisted that real change needs to come through lobbying Harrisburg to allow Philadelphia to enact stricter gun laws, which it can't do now. He has also proposed assigning assistant district attorneys to specific neighborhoods, so they could get to know the players -- both good and bad -- in a particular community.
On Yom Kippur, Williams paid a visit to Congregation Beth Solomon Kolel and Community Center in the Northeast.
"Whether you are Christian or Jewish, everyone wants the same thing," he said. "Everyone wants a good job, and to go home to their families and be safe."