Young foes eye an upset of embattled Wilkerson
If delegates from the Second Suffolk Senate district felt a little squeezed last weekend at the Democratic State Convention, it wasn't just because the chairs were packed so tightly on the floor of the DCU Center in Worcester. It was also because the delegation included both the district's reigning state senator and a hard-charging young challenger looking to unseat her.
Dianne Wilkerson arrived in office 14 years ago pegged as a rising star with limitless potential. But the Roxbury lawmaker has made headlines just as often for her legal lapses and self-inflicted wounds that have foreclosed bids for higher office.
Wilkerson had already drawn a Republican opponent this spring who is hoping to capitalize on her checkered record. But the seven-term senator could now be facing a far more serious threat in the heavily Democratic district: a feisty challenge from within the ranks of Democratic Party activists at a time when some are growing weary of Wilkerson's seemingly endless ability to shoot herself in the foot.
Sonia Chang-Diaz , who works for a local foundation that promotes the cause of women candidates for political office, is taking that mission to heart by jumping into the Senate contest.
``I have been frustrated with the standard of leadership this district is getting," says Chang-Diaz. ``Every voter should expect more from their leaders."
Chang-Diaz, who shares Wilkerson's liberal stands on most issues and, like her, cast a vote for Deval Patrick at the state convention, becomes the third declared candidate in a field that easily tops the diversity scale of any legislative race this fall. The 28-year-old Jamaica Plain resident, whose mother is white and whose father is a Costa Rican native of mixed Latino and Chinese ancestry, joins Wilkerson, the state's only African-American state senator, and Republican Samiyah Diaz , the daughter of Trinidadian immigrants.
As if the potential for voter confusion wasn't great enough in a race featuring a Diaz and a Chang-Diaz, all three candidates are now mounting write-in campaigns to secure the Democratic primary nomination.
The looming write-in showdown is itself a product of Wilkerson's latest misstep -- her failure to execute the usually rote task of gathering enough valid nominating signatures to appear on the September primary ballot. Wilkerson's campaign submitted 491 signatures minutes before the May 2 filing deadline, but the city election department ruled that almost half were invalid, leaving her short of the 300 required signatures.
Initially, that meant that Wilkerson would have to get at least 300 write-in votes in the September Democratic primary in order to appear on the November ballot as the party's nominee. But with a slot already secured as the Republican nominee on the November ballot, Samiyah Diaz announced last month that she would also compete in the Democratic primary, hoping to beat Wilkerson in the write-in contest and effectively capture the seat by claiming both the Democratic and Republican nominations.
But Diaz's quixotic quest to win Democratic primary votes as a moderate Republican may be overshadowed by the emergence of a true Democratic Party challenger.
Chang-Diaz, whose political credits include working as campaign manager for a losing 2004 state Senate campaign and as Election Day coordinator for a winning Senate special election last year, is well schooled in the brass tacks of campaign organization. And she may be able to generate some fund-raising firepower thanks to Barbara Lee , the wealthy Cambridge activist whose foundation works nationally to promote women political leaders.
Lee, who plans to host a June 19 fund-raiser for Chang-Diaz, calls her ``smart and talented and not only energetic but tireless."
``I usually don't take sides in a race with one progressive woman running against another," said Lee. ``But I've always known she was going to run for office, and said when she was ready to, I would support her."
Despite the assets, literal and political, that Chang-Diaz may bring to the table, it will be no easy task to unseat the charismatic Wilkerson, the state's most prominent black elected official and someone who has managed to get things done on Beacon Hill despite the swirl of controversy that often seems to surround her.
``People I talk to are pretty much going to be in lockstep in support of Dianne," said former city councilor Bruce Bolling , seated in the thick of the Second Suffolk delegation last Saturday.
But Bolling, the son of a prominent Roxbury political family, may be talking to only one segment of the sprawling and diverse Senate district, which includes all of Chinatown, the South End, Fenway, Roxbury, and Jamaica Plain, and parts of Dorchester, Mattapan, Back Bay, and Beacon Hill.
Talk to others across the district, and it's clear there is a degree of Wilkerson fatigue in the land that may only be growing. Brad Johnson , a South End convention delegate and organizer of the local chapter of Democracy for America, a grass-roots group formed out of the Howard Dean presidential campaign, expressed amazement at the string of miscues that have dogged the 53-year-old lawmaker. ``Any one thing isn't that much," said Johnson. ``But at some point all the little things add up, and Senator Wilkerson fits that mold."
That tally includes a 1997 sentence of six months' house arrest and a $2,000 fine that Wilkerson paid after pleading guilty to federal income tax charges. In 1998, Wilkerson paid $11,500 in civil penalties to settle a case involving allegations of irregularities in her campaign finance account. In 2000, she faced foreclosure proceedings for failing to pay her mortgage, but was able to halt the move without losing her condo.
And she is currently facing a civil lawsuit filed last fall by Attorney General Thomas Reilly involving new allegations of improprieties in her handling of campaign contributions and expenses.
``Dianne is a good legislator, but you are hearing people saying, `enough already,' " said Francesca Fordiani , a JP resident who waged an unsuccessful bid for City Council in 2003 and says she is still undecided about the who to back.
Alvin Shiggs , the chairman of Chang-Diaz's campaign committee, calls her someone with ``fresh ideas" who can give the district a fresh start.
An African-American retired Boston public schools administrator who served as cochair with Chang-Diaz of the parish council at St. Mary of the Angels Church outside Egleston Square, Shiggs said, ``I would not deny for one minute that Dianne has done a lot of wonderful things for the district." But with her series of self-inflicted wounds, ``clearly Dianne has hurt herself," said Shiggs. ``I've always believed when you can't do for yourself it makes it difficult to do for others."
That's an assessment Wilkerson would certainly take issue with. She points to a string a policy achievements over the years, including passage of the nation's first community reinvestment act requirement for insurance companies, and attention to district needs ranging from winning appropriations for a local skating rink to increased funding for Metco, the program that buses minority Boston school children to suburban school districts.
Standing on the convention floor last weekend, Wilkerson projected an air of confidence about the race. ``I am going to keep my seat, I have no doubt about it, by taking the campaign to the voters based on what I have done for them," she said. ``If there is a candidate who thinks they have a message they can take to the voters than will resonate, I say more power to them."
``It's certainly uphill," concedes Chang-Diaz. ``But the fact that no one's name is on the ballot certainly levels the playing field."
``I'm sure she's going to take this very seriously -- and she should," Jovita Fontanez , a veteran South End Democratic activist and onetime city election commissioner, said of Wilkerson.
Asked whether it was fair to question her ability to organize an effective write-in campaign given her failure to gather enough valid signatures to appear on the ballot, Wilkerson could only offer a curt,
Michael Jonas can be reached at jonas@globe.com. 
