The bug turned up on the eve of his re-election in 2003, uncovering a sweeping corruption probe that targeted, among others, his treasurer and a top fundraiser. The investigation netted nearly two dozen people, many closely linked to Street, whose second term ends Wednesday.
"He was very respectful of tradition by not being aggressive against corruption," said Randall Miller, a St. Joseph's University political analyst. "He's so tarred with that that no matter how many times he goes in the water, it's still sticking."
But the 64-year-old former city councilman will also leave behind a record of concrete and mortar in the nation's sixth-largest city, much of it from work early in his first term.
Street earned many supporters with a $300 million anti-blight initiative. The program started fast, replacing abandoned buildings with community centers and other projects.
In South Philadelphia, two new stadiums for the NFL's Eagles and MLB's 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.
His first-term crime initiative, "Safe Streets," evicted hundreds of open-air drug markets from tough neighborhoods. Progress later stalled amid concerns about police overtime.
Street, the city's second black mayor, helped ensure that George Washington's slaves will be commemorated in a memorial at the former presidential mansion near the Liberty Bell.
But Street also generated racial controversy. 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 claiming more than $111,000 in raises he had forgone since 2004. He said the city's finances were now healthy enough for him to accept the raises retroactively.
The number of homicides in the city dropped to 288 in 2002, their lowest number in more than a decade. But many will remember Street for the spike in 2006, when the tally broke 400 for the first time in nine years.
The mayor called gun violence a national problem. He pointed out that homicides were nowhere near where they were in 1990, when the total hit 500.
"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."
Street did not respond to interview requests from The Associated Press to discuss his terms in office, but his staff released a 12-page document listing his accomplishments. In it, his aides pointed out that 2007 homicides dipped slightly and other serious crime has been declining for seven years.
"The Philadelphia we leave behind is a lot better than the Philadelphia we found," the document said.
Many of Street's accomplishments would be eclipsed over time by the bug. The discovery, made during a security sweep, uncovered a four-year probe of the city's pay-to-play corruption. The mayor was never charged.
Public unrest came to a crescendo in his second term.
Although the city charter prohibited Street from seeking a third term, political adversary Michael Nutter, a former city councilman, swept to victory in November on an anti-Street campaign. He blamed his fellow Democrat for allowing corruption to persist at City Hall and not doing enough to end gun violence.
Street's supporters say his efforts are only now beginning to take root.
They argue that his legacy will not be determined until after programs aimed at decreasing truancy, finding jobs for at-risk adolescents and getting guns off the street have time to take effect.
"Some of the stuff that he's initiating now, we won't see the results of for two or three years," said Bilal Qayyum, a co-chair of Men United for a Better Philadelphia.