Ed Rendell gets credit for bringing the city back from near bankruptcy when he was mayor in the 1990s, a record that helped lead him to the governor's mansion.
When it comes to Mayor John F. Street, whose second term ends Monday, it will be tough to get past the bug that the FBI planted in his office. The October 2003 discovery uncovered a sweeping corruption probe that targeted, among others, his treasurer and one of his biggest fundraisers.
The bug will be a big part of the complicated legacy that Street, who was never charged, leaves after eight up-and-down years in City Hall. But in time, it could also be shrugged of as just another blemish in the town Lincoln Steffens dubbed "corrupt and contented."
"He was very respectful of tradition by not being aggressive against corruption," St. Joseph's University political analyst Randall Miller said. "He's so tarred with that that no matter how many times he goes in the water, it's still sticking."
History will note that the probe netted nearly two dozen people, many closely linked to Street. But the 64-year-old former city councilman will also leave behind a record of concrete and mortar, much of it from a surge of activity early in his first term.
Street, an often prickly politician who once shoved a television reporter to the floor, made many friends with his $300 million anti-blight initiative. The program started fast, putting community centers and other projects in the place of abandoned buildings.
In South Philadelphia, two new stadiums for the Philadelphia Eagles and Philadelphia Phillies stand as reminders of another early success. Street announced deals to build them as replacements for aging Veterans Stadium, even though hopes for downtown facilities collapsed.
Street's first-term crime initiative, "Safe Streets," evicted hundreds of open-air drug markets from tough neighborhoods. But progress later stalled amid concerns over police overtime.
The city's second black mayor behind Goode, Street helped ensure that George Washington's slaves will be commemorated in a memorial at the former presidential mansion near the Liberty Bell.
But he spawned racial controversy, too. In 2002, he galvanized opponents by telling an NAACP conference: "Let me tell you: The brothers and sisters are running the city. ... Don't you let nobody fool you; we are in charge of the City of Brotherly Love." He later apologized.
On his way out the door, Street raised eyebrows by deciding to claim more than $111,000 in raises he had foregone since 2004. In the midst of his re-election in 2003, he vetoed a bill that would have boosted his salary from $146,000 to $165,000. Responding to public criticism last month, he said the city's finances were now healthy enough for him to accept the raises retroactively.
Many of his successes and mini-controversies, however, could be eclipsed over time by the bug.
The discovery, made during what police called a routine security sweep, uncovered what would be a four-year probe of the city's "pay-to-play" corruption. Treasurer Corey Kemp was convicted and Ronald White, a top Street fundraiser, was a main target before he died awaiting trial.
The bug's discovery was breathtaking, but hardly tragic like the MOVE firebombing on Goode's watch in May 1985. After police dropped the explosive on the militant, back-to-nature group's West Philadelphia house, a raging fire killed 11 people, including five children.
Nor was Street as racially divisive as Rizzo, whose crime crackdown in the 1970s infuriated blacks across the city.
Murders dropped to their lowest point in more than a decade in Street's third year: 288 in 2002. But many will remember him for the spike in murders during his second
term, when the homicide tally broke 400 for the first time in nearly a decade.
"The first couple of years I think he did a great job in attacking the crime and gun violence," said state Rep. Jewell Williams, D-Philadelphia. "But after the Safe Streets everything seemed to collapse."
The mayor bristled at the barrage of criticism, calling gun violence a national problem. He pointed out that murders were nowhere near where they were in 1990, when the total hit 500.
The spike prompted an outcry from a frustrated District Attorney Lynn Abraham, who implored Street at a news conference to "Do something!"
When asked for an interview to discuss his two terms in office, Street's office released a 12-page document listing his accomplishments. In it, his aides point out that homicides are slightly behind last year's pace in 2007 and that other serious crime has been declining for seven years.
"The Philadelphia we leave behind is a lot better than the Philadelphia we found," it said.
Street, who has had an adversarial relationship with the press, did not respond to interview requests from The Associated Press.