The Hill and the Hall Week in Review

Each Friday, Paul McMorrow will take you inside the smoke-filled rooms and darkly-lit corridors of government to bring you the hottest and juiciest political tidbits. This week: The mayor fattens his war chest, and Sen. Dianne Wilkerson continues to sweat.

Let’s start by picking on Hizzoner. Nothing gets the natives riled up like parking tickets, so Mayor Tom Menino’s $2.42 billion FY09 budget, which includes $13 million in new parking fines, is sure to be the only thing anybody in Boston ever talks about for the rest of time. Let the schools close; we demand parking amnesty now!

But seriously, the notion that the mayor is sewing great harm by balancing Boston’s budget on the backs of people who can’t manage to avoid parking in front of fire hydrants, rather than slogging through a nasty override fight, is about as dumb as the notion that kids wouldn’t be killing each other if it weren’t for these infernal T-shirts and video games. Gotta love this town.

In other City Hall news, the people who work inside City Hall still suck, just like they always have.

Are your civic outrage juices flowing? If so, please send some money to Michael Flaherty. The guy is really gonna need it. He’s not even officially in the mayor’s race yet, and it already appears that his fundraising base might be in danger of drying up.

Flaherty took in a little over $60,000 during the year’s first three months. Pocket change. He spent nearly $43,000 of it, and has around $450,000 in cash-on-hand. That’s in keeping with his 2007 fundraising patterns, when he didn’t really start raising money until May, taking in the bulk in the fall.

A look at Mayor Menino’s finances should throw a wicked scare into the Southie city councilor. The mayor has been raising money at a furious pace this year. He ended 2007 with over $973,000 in the bank, and through the end of March, had added $282,569 to that total. He has spent twice what Flaherty has – $86,000 – but has also socked away $650,000 in savings, investing in CDs and money market accounts.

Flaherty pounced on the 311 and parking ticket stories in this week’s papers, issuing a pair of press releases blasting the administration’s ineffectiveness. He has also been an outspoken (occasionally shouting and red-faced) opponent of towing. This suggests he may try to run a populist, nuts and bolts campaign, and try to out-mechanic the urban mechanic.

There’s no way Flaherty outspends Menino in this race. The mayor out-gunned him three to one last year, and that was during a City Council election. But it’s critical that he get whatever receipts he can this year, because once he is officially in this race, the pool of saps willing to cross the mayor and give money to him will only get smaller. (This is also one reason why observers believe Flaherty won’t, and can’t, declare his candidacy until after Labor Day.)

It seemed that if Dianne Wilkerson couldn’t lose last year – a year in which the powerful but embattled state senator couldn’t manage to wring 300 good signatures out of her sprawling district, and had to wage a high-wire write-in campaign against a two-headed Diaz monster and an old cop. All that self-destruction, the money troubles, the staggering sense of entitlement conveyed by the signature fiasco – and none of it seemed to matter. The woman was invincible.

Invincibility isn’t protecting her, though. Wilkerson looks to have two challengers this fall. JP’s Sonia Chang-Diaz is once again gunning for Wilkerson in September’s Democratic primary. An independent candidate, William Theodore Leonard, will sail into November’s election. That’s assuming, of course, that everyone involved can get signatures in by the end of this month. It shouldn’t be a significant hurdle, but for some reason, it is.

A third would-be challenger, Robert Patton-Spruill, pulled nomination papers for the seat but recently decided to shut down his nascent campaign and go to work for Chang-Diaz.

The Roxbury filmmaker (he shot Tim Murray’s campaign commercials, and his Public Enemy: Welcome to the Terrordome debuts this month at the Independent Film Fest) began gathering signatures and says his campaign could’ve been competitive, but backed out when he decided he’d be “better off using my skills behind the scenes.” And he maintains that, with more time to organize this time around, the Chang-Diaz campaign can do more than just throw a scare into the eight-term senator.

In Jamaica Plain, Patton-Spruill says Wilkerson “has issues.” He also insists that “We can be strongly competitive in Roxbury.” They’ll have to be; Chang-Diaz got rolled on Wilkerson’s turf two years ago, and it cost her the race. “African-Americans of my generation are looking for change,” Patton-Spruill says. “They’re upset at the current black leadership on Beacon Hill. The whole country is looking for new youthful voices.”

That’s some Deval Patrick Just Words stuff right there, and it’ll be fascinating to see if a netroots organizational machine can be deployed with any success at the ward level. Patton-Spruill will be building an online broadband channel for Chang-Diaz, and loading it with long-form videos – “on demand” campaigning to “show the real Sonia” and help fuel shoeleather politics.

For this campaign to work, Chang-Diaz has to make the conversation about youth, hope, change and the like. Because, otherwise, commentators will look to the 2006 results and frame the election as a race about skin color, class, and neighborhood division. And that’s certainly not a conversation many people are eager to have anytime soon.

Neither woman has to file paperwork with OCPF until the fall, so until then, we’ll all have to be content with trolling through their 2007 off-year campaign finance reports.

One big difference: Wilkerson blew through nearly $34,000 in a non-election year by spending on staffing, fundraising, phones, food, and airfare. Chang-Diaz spent $618.

The off-year donor lists are interesting as well. Chang-Diaz got money from big names like Barbara Lee, former Menino aide Howard Leibowitz, and Micho Spring in 2007. Wilkerson received support from a buttload of labor unions, as well as Bruce Bolling, John Nucci, Maura Hennigan, lobbyist and former House Speaker Charlie Flaherty, Angela Menino, Susan Passoni, BRA planner Muhammad Ali-Salaam, Jerry Rappaport, Jr., Chris Iannella, and two members of the troubled Winn clan.