Street was elected to the 181st District of the Pennsylvania House of Representatives as a Democrat in 1978, and to the Pennsylvania State Senate as a Democrat in 1980. However, shortly after his election, he switched parties to a Republican in order to give the Republicans control of the State Senate. He was rewarded with a committee chairmanship and a finer office that was previously State Senator Vince Fumo's. He was an unsuccessful candidate for Congress against incumbent RepresentativeBill Gray in 1982, and an unsuccessful Democratic candidate for re-election as State Senator in 1984.
2007 Mayoral candidacy
Street declared his candidacy in the 2007 Philadelphia mayoral election, while awaiting his trial. His candidacy was denounced by many, including eventual Mayor Michael Nutter, who called Street's candidacy a distraction from important issues. Street was later arrested on February 19 in New Jersey for failure to pay multiple traffic tickets, though he asserted upon release that his campaign would continue. Street had announced that if 5,000 people did not attend a noontime rally at City Hall plaza on March 1, 2007, he would give up his candidacy for mayor. Media reports placed attendance at about 200, many of those curious passersby. Street was undeterred, saying he "underestimated" his passion and vowed to continue in the race, not wanting it to be considered a "publicity stunt."
Five days later Street withdrew, announcing his intention to run for one of the five Democratic at-largecouncil seats on the last day to file nominating petitions. This would place him in contention with his nephew, Sharif Street, son of the former mayor of Philadelphia. Street himself pointed out that the city residency requirement for a council candidate is one year instead of the three years for a mayoral candidate. There has been some question as to where Street officially resides, in Philadelphia or Moorestown, New Jersey. On March 12, 2007, Street's petition's was challenged in court by a voter, since Street turned in only 894 validated signatures into City Hall and the requirement to be placed on the Democratic Primary ballot is 1,000. He did get on the ballot and was unsuccessful in his bid, finishing 17th of 19 candidates with 1.47% of the vote.
2011 Mayoral candidacy
Street was once again running for mayor in the 2011 election. He challenged incumbent mayor Michael Nutter in the Democratic primary, and lost, accumulating 24.07% of the primary vote.
2015 Mayoral candidacy
On March 10, 2015, Street filed as a Democratic candidate for mayor of Philadelphia. As with previous years, violence prevention was a central theme of his campaign. He received 1.68 percent of the vote, finishing last in 6th place. Shortly after his failed campaign, Street announced a proposal to train 5,000 residents in martial arts to support law enforcement.
2018 State House campaign
Street ran for his old seat in the 181st Pennsylvania House district as the Republican nominee. He received 4.66% of the vote, losing to Democrat Malcolm Kenyatta.
2019 mayoral candidacy
On May 15, 2019, Street announced his candidacy in the 2019 mayoral election. Having announced too late to run on either party's ticket, he ran an independent write-in campaign. He had until August 1, 2019 to submit the necessary paperwork and petition with the required signatures.
During his trial, Street used the tax protesterargument that the federal income tax on wages is illegal, saying: "I could not find in the IRS code the statute that authorizes the Internal Revenue to levy and collect a direct tax on the American people's wages. And I will say to you, if you find that law for me and bring it in here for me, I will plead guilty to all these charges." On February 22, 2008, Street was convicted of three counts of tax evasion for years 2002, 2003 and 2004. He was acquitted on mail and wire fraud charges. Street was sentenced to serve 30 months in prison. Street appealed, but his conviction was affirmed by the Third Circuit Court of Appeals.
