He's been a state legislator, a hot-dog vendor, and a longtime political activist in Philadelphia - and now, T. Milton Street Sr. is a federal prisoner.

Street, 69, the older brother of former Mayor John F. Street, was led off in handcuffs yesterday to start serving a 30-month prison term for failing to file federal tax returns for three years.

"Outrageous," was how U.S. District Judge Legrome D. Davis described Street's failure to file returns or pay taxes on nearly $3 million in income. "It's too much money not to pay a penny of tax on," Davis said just before imposing the sentence.

Davis also ordered him to pay $413,000 in back taxes.

Street, who lives in Moorestown, showed no emotion as the sentence was announced. He remained stoic as he was cuffed and led from the courtroom after turning over his watch, tie and other personal items to his visibly shaken wife, Theresa.

Moments earlier, Street had asked Davis to allow him to perform community service in lieu of a prison sentence.

"I submit to you, your honor, even though I may deserve to go to jail . . . I can do so much more by serving 10,000 hours of community service," Street told the judge. "I ask you for mercy."

The sentence was near the maximum three years sought by federal prosecutors, who had argued that such a term would deter others from similar crimes.

"Tax cheats must be put on notice that there are severe penalties, including years in prison," Assistant U.S. Attorney Jennifer Arbittier Williams told Davis.

The former Democratic state representative and senator had been found guilty in February of three misdemeanor counts of failing to file federal tax returns, but acquitted of fraud charges in an alleged scheme to sell an airport-maintenance contract.

"I am a good man, your honor," said Street, who said he had always tried to work on behalf of the poor and people facing other struggles.

Davis agreed that Street had done many good things, but concluded that he had "squandered" the trust his one-time constituents had placed in him.

"It's a violation of the trust of those people for you to so foolishly throw yourself off the cliff," said Davis, who said that Street had had opportunities to "do some really really good things" but had been sidetracked by the "ridiculous amounts of money" people were paying him.

Referring to Street's testimony during trial that he wanted to take advantage of his brother's term as mayor to get consulting contracts, the judge said those days should be over in Philadelphia.

"The city deserves better than people lining their pockets because of relationships," Davis said.

Davis repeatedly asked Street why he hadn't paid his taxes when he was making a substantial income. Street said he had procrastinated. "I was spending cash like a faucet," he told the judge.

In a sentencing memorandum, the prosecutors contended that between 2000 and 2004, Street received nearly $3 million in income from Philadelphia-area businesspeople who chose to pay him as a consultant "due in large part to Street's relationship with his brother, the Mayor of Philadelphia."

The former mayor was not in the courtroom during the nearly five-hour sentencing hearing, and he did not return e-mail and phone messages.

While Williams and Assistant U.S. Attorney Anthony J. Wzorek had asked Davis to impose the maximum sentence, defense attorney Jeremy H.G. Ibrahim asked for a more lenient sentence, such as house arrest.

"We are only imploring the court to consider other aspects of Mr. Street's life," said Ibrahim, noting Street's years of civic activism.

He also asked the judge to allow Street to remain free pending the outcome of an appeal, or to surrender in coming weeks.

Wzorek urged the judge to send Street off to prison - immediately.

"This is his day of judgment, and I would suggest to the court it's time for him to go," Wzorek said.

The judge agreed.

"Good luck, Mr. Street," Davis said as the hearing concluded.

Williams called the 30-month prison term an "appropriately serious sentence for serious criminal conduct."

She said the sentence showed: "You have to pay your taxes - it doesn't matter who you are."

Contact staff writer Emilie Lounsberry at 215-854-4828 or at elounsberry@phillynews.com.