What’s wrong with this picture?

It’s Milton Street, the long-shot, bad-boy candidate for mayor of Philadelphia getting one of two major union endorsements over the past week.Street appeared with firefighters’ union president Bill Gault yesterday afternoon, only hours before speaking to delegates of the city’s largest union, AFSCME District Council 33, which endorsed him over Mayor Michael Nutter.

There’s a long tradition in Philadelphia of city unions endorsing opponents of incumbent mayors. After four years, they’re usually pretty ticked off at the guy they’ve been negotiating with, and this election is no exception.

District Council 33 is going on two years without a contract, and Nutter says he needs some meaningful changes in pension and benefit packages before he’ll sign the deal. Firefighers are furious over Nutter’s cutbacks in department staffing, and Street has promised to reverse course if elected.

I wasn’t able to reach DC33 President Pete Matthews last night, but you can get the gist of his feelings about Nutter in this piece I wrote after interviewing him a month ago.

I went to the firefighters’ endorsement news conference yesterday to ask union president Bill Gault a simple question: Do you really believe Milton Street, with his history of bad debt and bankruptcy, his prison term for failing to file tax returns, and his outstanding tax debt of more than $1 million can manage the city’s finances effectively enough to keep the promises he’s making to your members?

Because if I’ve learned anything covering elections for nearly 30 years, it’s that what a candidate has done is a far better measure of his worth than what he says he’ll do.

And while I find Milton smart, entertaining and often likable, he’s shown himself over the years to be anything but responsible.

Among the more memorable chapters in the Milton Street story:

– In 1989, Republicans made Milton an assistant budget director in traffic court in return for help he’d given them in the state legislature. He lost the post for failing to pay $2,000 in traffic tickets. “Why the f— should I pay?” he told an Inquirer reporter at the time.

– In the 1990s, Milton returned to street vending. Despite numerous citations by the Department of Licenses and Inspections, the Rendell administration in 1996 and ’97 put him in charge of controlling vending at the Penn Relays. The Penn’s Landing Corporation eventually took Milton to court for unpaid vendor fees.

– In 2000, political contributors got invitations to pay from $300 to $10,000 to sponsor a birthday gala for Milton’s brother, then Mayor John Street. It turned out the money was to go to a new political committee registered to Milton and an associate, and the mayor didn’t even know about the event. He pulled the plug on it.

– In 2005, Milton admitted in court papers he’d been paid $30,000 a month as a “consultant” for three years by a company whose only business was a $13 million a year contract airport maintenance contract with the city, while Milton’s brother was mayor.

– Later that year, Milton declared bankruptcy. Though he kept a Philadelphia voting address, he listed his address in the bankruptcy filing as Moorestown, New Jersey.

– In 2006 he was indicted by a federal grand jury on fraud and tax evasion charges. He was eventually cleared of everything but failing to file tax returns for three years, for which he served a 30-month prison sentence.

Yesterday, Milton stood in a conservative business suit and humbly accepted the firefighters’ endorsement. When I asked union president Bill Gault my question – whether he seriously expected this candidate to do something for his members – Gault said a lot of people have made mistakes, and Milton knows a few things.

“He didn’t pay his taxes on time and he’s had his reasons to do that,” Gault said. “He has the ability, he’s been a state legislator, he’s been a state senator. He has the ability, he’ll find the money.”

But talking with Gault afterward, he was more pragmatic. He truly believes staff shortages are putting the public and his members in danger, and he’s desperate to bring attention to the issue. Looking at the assembled media, he said, “if we hadn’t done this, none of you guys would be here.”

An independent study has been commissioned to look into department staffing and service levels and whether the public is adequately protected. Gault says in the meantime, he’s going to keep making noise about the issue.

“I’m just looking out for my members,” he told me and two other reporters. “If any of youse were in my shoes, you’d be doing exactly the same thing.”