Is This Woman Paranoid? Or Are People Really Out to Get Her?

State Senator Dianne Wilkerson is black. Very black, crude as that may be to say in a society that claims to overlook racial differences. So black that, now, as she stands up on the dais of the Massachusetts Senate chamber, its circular walls painted a robin's-egg blue that matches the state flag, her distinctive features undergo a curious transformation. Up close, Wilkerson's face is immensely expressive, with imploring eyes and a mouth that can convey everything from exasperation to delight without emitting a word. But when I view her from the visitors gallery, all that disappears. From here, Wilkerson becomes what she is for most people: her face, her self, a smudge of blackness, little more.

It's the blackness of her race, yes. But it is also the blackness of mystery. She is the highest elected black official in the state, and the first black woman ever elected to the state Senate, where she is now also the only black member, making the other 39 seem pale and rather lifeless by comparison. Though considered, early on, a politician of enormous promise, one who might ascend to Congress or the mayor's office, she is also a woman who seems to have displayed a self-destructive streak. She failed to pay her taxes and has been accused of failing to pay her bills and parking tickets. She was found to have misused campaign contributions and violated legislative ethics laws. In a place where few people know the names of their own state senators, she is a lightning rod who instantly provokes strong feelings, and often derision, even outside her district. Yet, despite everything, “I pinch myself sometimes because I really can't believe I'm here,” she says gaily. “I told my minister that I was worried I wasn't worried, and he just laughed and said, 'Dianne, most people spend their lives trying to get to that place, and it's okay.'”

It has, in fact, been quite a rise for a woman who first came to Massachusetts at age five in flight from Pine Bluff, Arkansas. There, in the 1930s, two uncles had defied custom by refusing to drive their buggy off the road when a couple of white men approached in their car. Outraged, the whites opened fire, and the uncles responded in kind—with more-accurate shots. Nearly lynched, they were sent to prison for almost 20 years for murder, and when they were released in the late '50s, Uncle Albert went as far west as the train would take him, ending up in Oakland; Uncle Willie, with Dianne's family in tow, as far north, to Springfield. Raised there as the fourth of 12 children, she was the only one to go to college, which she followed with Boston College Law School and a stint at a downtown law firm before serving as counsel for the local chapter of the NAACP and beginning her political career.

Wilkerson herself has encountered racial hostility, in this once proudly abolitionist city. She was showered with racist obscenities, cigarette ashes, and spit at a restaurant in Harvard Square in 1978. She was treated with humiliating disdain, by her account, when, as assistant counsel to then Governor Michael Dukakis, she had the temerity to show up, the only black, the very first black, at her local Democratic caucus in South Boston in 1986. (She got her revenge, she says, when she persuaded the party convention in Springfield to deny the South Boston delegation's credentials the following year, when Dukakis ran for president. Were there repercussions from that? “I'll never know,” she says. Then she checks herself. “Of course.“)

With its mingling of public triumph and even-more-public suffering, Wilkerson's is a great and peculiarly Bostonian drama, one akin to, though far less well known than, the darkly Hawthornean tale of the joined-at-the-hip Bulger brothers, one a gangster, the other a Senate president. As the Bulgers were products of the special constrictions of Irish Catholics, whose career choices seemed often limited to politics, crime, and the church, so is Wilkerson the result of the race legacy by which blacks are still, deep down, presumed to be shady, unreliable figures in this city, no matter how much right-thinking people may profess to accept them. Unlike the Bulger brothers' tale, though, Wilkerson's has never fully been told.

Wilkerson was tagged early in her political career as a tax cheat for failing to file her taxes in the early '90s. This occurred after she had pushed through one of her first major bills, forcing insurance companies to reinvest in inner-city neighborhoods where, Wilkerson's analysis showed, they were extracting nearly $1 billion in premiums. Wilkerson admits to not filing her taxes in 1991 and 1992. “I didn't have the money,” she says with a shake of her head, owing in part to having taken in the two children and grandchild of a sister who had a drug problem. She insists she received extensions for 1993 and 1994, although she ended up pleading guilty to failing to pay her taxes all four years because, she says, it would have cost $100,000 to fight the charges, and if she'd had that much money, she would have paid the taxes on time to begin with.

It apparently was the first time in state history that a public official was prosecuted criminally for failing to file a tax return. That year 11 other legislators were discovered to have committed similar infractions without receiving any penalty. Even state Representative Marie St. Fleur's tax problems might not have surfaced if Attorney General Tom Reilly hadn't picked her last month, briefly, to run as his candidate for lieutenant governor. Placed under house arrest for six months, Wilkerson was also hit with nearly $150,000 in penalties by the IRS, which ratcheted up the initial case of negligence to one of fraud and incorrectly asserted in its official documents that she was a felon besides. (Under the tax code, failure to pay taxes is a misdemeanor.)

It took several years of negotiation, but the IRS ultimately withdrew the charge of fraud, having concluded there was no evidence that Wilkerson had tried to defraud the government by either living luxuriously or concealing income. “As I told them when we started, there's nothing there,” she says. “I have no money hid. What you see is what you get. There's no beach house. There's no boat. There's no secret account. This is it.” Her attorney in this matter, Paul Saba, says he was struck by the attitude of some of the officials in the case: “One was professional, but others displayed what seemed like a visceral, irrational hostility toward her, and took action against her based on allegations they should have known to be untrue.”

The tax charges coincided with the opening up of Joe Kennedy's congressional seat, for which Wilkerson was widely conjectured to be a candidate, since her Senate district is entirely contained within that congressional one. She did not run for Kennedy's seat, which was won by Somerville Mayor Michael Capuano with fewer votes than Wilkerson received that fall as state senator. “The more I stay under the radar screen, the better I do,” she says. “The minute I stick my head up—pchew!”

The charges also softened her up for subsequent claims, ones that have created the impression that where there is so much smoke, there must be fire. Indeed, the standard reaction to Wilkerson from people who know her from press reports is a sigh, a shake of the head, and idle allusions to some tragic flaw. The near-total disconnect between the generally negative public perception of a politician who is so widely vilified and the different impression made by a close examination of Wilkerson's story leaves me uneasy. Am I crazy to believe her? More to the point, are you now crazy to believe me? 

It is true that the sheer number of allegations over the years gives pause. As a practical matter, Wilkerson has become a magnet for prosecutors. None of the charges has any of the shocking seriousness of, say, having oral sex with an intern in an Oval Office anteroom, or driving off a bridge into Chappaquiddick Sound and leaving a passenger to drown. But they have lodged in a deep place in the collective Boston psyche all the same. After those first allegations hit home, the burden of proof shifted, and Wilkerson became guilty until proven innocent.

There was, for example, the 1998 charge by the Office of Campaign and Political Finance that she illegally used campaign funds to cover personal expenses. Which sounds bad, until you discover that it involved payment for a skirt suit she wore to campaign events. She considered the suit akin to the rented tuxedos male candidates legally charge to their campaigns. The campaign finance office disagreed and demanded restitution, plus $11,500 in penalties. (The skirt suit cost $500.)

These charges, in turn, made it seem all the more likely that something was amiss when the state Ethics Commission fined Wilkerson in 2001 for failing to disclose $20,000 she'd received from the then Boston Bank of Commerce for consulting services—even as, she says, the commission gave, in Kafka-esque fashion, explicit permission to provide those services. If she'd never gotten into trouble before, you'd probably have overlooked that. Do you now? She made the papers again that year when her condominium association sued her for failing to pay $4,671 in condo fees, though she said she was withholding them for poor service. The $1,300 in parking tickets she supposedly ran up? She insists they were her sons'. Fox 25 News knew her car had been towed before Wilkerson did.

And so on, until this fall, when Attorney General Reilly charged her with being “unable or unwilling” to report or explain what had happened to more than $45,000 in missing campaign funds she had first been notified about, the press release claimed, in August 2002. This complaint was far more detailed than a so-called draft report Wilkerson had been presented the previous November—which she says she had been working to respond to. It focused on her employment of her sons, Kendall and Cornell Mills (they take their last name from their father), in the Democrats' coordinated 2000 campaign, of which Wilkerson, at the behest of the Al Gore campaign, took charge. No allegation against them was specified, only that Wilkerson failed to explain what they actually did. Both had served in all but one of their mother's campaigns, most recently as field directors. Two weeks later, as if to explain what the beef was, someone tipped the Boston Globe to the fact that Cornell Mills had been hired by Suffolk County District Attorney Daniel Conley as a civilian investigator despite having been arrested at least four times. Sounds bad, right? But at least five of the 279 employees in the DA's office had arrest records; none of Cornell Mills's arrests had led to convictions; and there was no evidence that Conley had been pressured by Wilkerson to hire her son, or that Cornell was unqualified.

But this is a political season, and Reilly is, of course, running for the Democratic nomination for governor. He is opposed by Deval Patrick, former head of the civil rights division in the Clinton Justice Department. Patrick is so closely linked to Wilkerson that one media account erroneously referred to them as married. (Patrick is married to another lawyer named Diane.) By this line of thinking, an attack on Wilkerson is a knock against Patrick. As soon as Patrick heard about the charges, he called Wilkerson. “Is this about me?” she says he asked. Wilkerson had to agree it was a possibility.

At 6:41 on the morning after the attorney general filed his charges, Wilkerson received an e-mail with the subject “You.” It read:

Ms. Wilkerson: You are a fucking disgrace. If you had any sense of honor, you'd resign your position. And your constituents are even stupider than you are, electing you term after term. Go away.

As communications to Wilkerson go, this one actually was not all that extreme. There was a period in the late 1990s when her mail was so toxic, then Senate President Tom Birmingham had it opened by security officers. This particular missive would not have held Wilkerson's attention, except that a constituent recognized the last name in the e-mail address. It was an unusual last name, the same as that of an investigator who works for Reilly. Curious about this, I wrote to the address myself, but received no reply. I asked the Attorney General's Office to determine whether that particular investigator had sent the e-mail. A spokeswoman declined, saying public employees have the right of free speech, but added that the investigator with the same last name as Wilkerson's antagonist was not involved in her case and would not be asked if he had sent the offending e-mail. “The attorney general finds the e-mail offensive and inappropriate, and it in no way represents the views of this office. The time and place of this message, however, prevent us from treating this as an office matter and taking further action.”

There is yet another side to this story, or, more exactly, another story altogether. Since her first upset win in 1992, Wilkerson, who is now 50, has been routinely reelected by margins so wide that she ran unopposed in the past two elections, one of only a few senators in the state to face no competition. Even in 1998, just after she'd served six months of house arrest for the tax charges, and when both the Globe and the Herald were calling for her head, she trounced her strongest challenger, a Haitian-American aide to House Speaker Tom Finneran who the Globe and Herald both endorsed.

Why, despite the cloud that hangs over her, does she remain so popular with her constituents? Again, the general suspicion is that in the morally inverted world of the 'hood, anybody so bad must be good. And she is standing up to the Man. But there is one discordant fact: By consensus of her fellow legislators, Dianne Wilkerson is a singularly able senator, pushing through legislation, attending to her core constituency in Roxbury and Dorchester, serving as the unofficial senator of all blacks outside her district, too (since they often don't trust their own representatives), and taking on extras like persuading Houston victims of Hurricane Katrina to come to Massachusetts, as she did last fall.

This has mostly escaped the attention of the city's dailies. But let Senate President Robert Travaglini tell it. “The view of Senator Wilkerson's colleagues is this: She is very articulate, very passionate about issues she cares about, extremely accomplished, and somebody you don't want to tangle with.” How many other legislators are like that? “A handful.” He laughs. “And I'm being kind.”

Mayor Tom Menino spent the first five years of Wilkerson's tenure without speaking to her, according to Wilkerson herself, and refusing to appear at any public function where she was expected, so angry was he that Wilkerson had endorsed his mayoral opponent, Jim Brett, shortly after she was first sworn in. (It didn't help that Wilkerson herself was touted as a potential candidate for mayor.) Now, Menino can scarcely contain himself, hailing Wilkerson as “one of the most hard-working elected officials we have” and “a voice of reason in the community.” He concludes: “Some people forget who sent them to the State House. Dianne doesn't. She never forgets.”

And so it goes, from Republican state senators down to Democrat Sam Yoon, the new city councilor from Chinatown, who considers Wilkerson an inspiration that drew him into politics.

Some of this enthusiasm, of course, is political calculation. It would be unwise to cross a woman who commands the voter loyalty Wilkerson does. But some comes from legislative accomplishments that go beyond what one might expect of a black state senator so tainted by scandal. She pushed through a reform of public construction regulations that affect several billion in state spending on everything from high schools to bridges, allowing architects, labor, contractors, and subcontractors to coordinate their efforts for the first time in the manner of private construction teams, at significant savings in time and expense. Irked that Viagra was covered by three-quarters of insurance companies but birth control pills by fewer than half, Wilkerson spearheaded legislation requiring that birth control pills be reimbursable, much to the consternation of the Catholic Church. She has likewise required insurance companies to follow the lead of banks and reinvest a percentage of the premiums they take out of urban neighborhoods, making Massachusetts the first state in the nation to do this. She pushed for data collection to determine the nature and extent of racial profiling, which did not please the police. “It was just the data!” Wilkerson exclaims. “Nobody is punished! I just wanted to see if we had a problem. Well, you'd think I'd asked the cops to hand over their firstborn children!”

If such accomplishments have been lost on the local populace, they have not escaped the attention of the national political leadership. When Gore was running for president, he was so eager to enlist Wilkerson's support he called her on her cell and her home phone after her office assumed that “Al Gore” was a crank caller and hung up on him. She was key to bringing the Democratic National Convention to Boston in 2004, and coveted by a John Kerry campaign eager to establish its bona fides with the black community. More recently, she came within a whisker of being elected vice chair of the Democratic National Committee, but was done in by the scandals that continue to trail after her like a tin can tied to a dog's tail.

The two versions of Senator Wilkerson, the good Dianne and the bad Dianne, are so widely divergent they may appear irreconcilable. Underlying both, however, is the undeniable fact that Wilkerson's personal finances are a mess. More to the point, Wilkerson is a powerful antagonist, unusually capable of pushing ahead with her agenda. “I just keep moving until people say I can't,” she says. It is quite possible that people love her and hate her for the same reason: She gets things done. Unfortunately for Wilkerson, the haters are powerful enough to threaten her in way that the lovers cannot always prevent.

This pattern was set early in her public career—on New Year's Day in 1991, to be exact. The night before, as counsel for the local NAACP, Wilkerson had secured a historic agreement from then Mayor Ray Flynn that the city would abide by a federal race-blind admissions policy for public housing, for the first time opening up South Boston projects to blacks and providing a half-billion-dollar settlement for any families that had been wrongfully excluded. At about 4 the next morning, Wilkerson was awakened by a telephone call from a man who did not identify himself but, in an eerily calm voice, said he had just come from a meeting in South Boston where five men had agreed to terms on a contract on her life. It was for $28,000, the man said, adding that this was more than they'd gotten for the hit on Whitey McGrail, a South Boston bookie who had been, Wilkerson happened to know, gunned down, possibly over a gambling debt, five years before. The contract called for Wilkerson to be dead by 8 p.m. Thursday, January 3—three days away.

Why? Wilkerson asked.

“Because there are too many fucking niggers.”

And why was he telling her this?

“Because I was cut out of the deal.”

Wilkerson called her friend Joe Carter, then deputy police superintendent (and now the MBTA's chief of transit police), and Carter dialed the police commissioner, Mickey Roache, who called Wilkerson and told her to stay away from her windows. Carter remembers the incident. With something like that, he says, “you take the damn thing serious.” Minutes later police were swarming into Wilkerson's house. They accompanied her when she left for work in the morning, carefully examining her car for bombs.

This episode established the fault lines for relations between Wilkerson and the city's two dailies. When she first spoke of the death threats, in 1997, citing them as one reason she had been overwhelmed by bills in 1991 and 1992 (she said she'd had to install an expensive security system and frequently take taxis), the press reaction was either black or white. White columnists at the Herald (Margery Eagan) and the Globe (Mike Barnicle) howled at her shameless race-baiting, since she'd mentioned that the assassins' meeting was in South Boston, and we all know what that's code for. Eagan slammed her “strange tales” and “cute excuses.” Barnicle sneered, “It's a perfect story. . . . It's got texture, although it does lack a bit of imagination. Not to mention any reliable witnesses.” Only black Globe columnist Patricia Smith rose to Wilkerson's defense. “The jackals are working overtime,” she wrote.

This did not stop Wilkerson from challenging the seemingly entrenched Bill Owens, an incumbent black state senator, and beating him easily. She has seemed preoccupied in office less with racial issues than with larger social ones. She has been an advocate for gay marriage, even though many black ministers, including hers, oppose it. She sees it as a civil rights issue, and spoke of it that way on the Senate floor, invoking the travails of her uncles in Pine Bluff as her reason to extend the equal protection of the law to homosexuals.

As Sam Yoon puts it, Wilkerson helped him see the racial divide as the “archetype” for “understanding and misunderstanding” all of this city's crazy-quilt ethnicities and interests. But however endearing this seems to her electorate, the approach has antagonized those powers invested in the status quo, and the list of the offended lengthens, bill by bill.

“Other people have endured much less, for a shorter period of time, and withered away,” she says. “Would I want life to be different? Not really. To change the bad things, I'd have to change the good things, too.” She still might like that congressional seat one day, and is building toward it by hosting the local segment on WILD-FM of a national black radio network. But for now? “The only thing I know how to do is to keep moving,” she says. She's going after the police for failing to require homicide detectives to work after 1 a.m. (a column she wrote for the Globe to this effect drew mainly criticism for misstating some facts), and making the small gestures, like helping the Dorchester woman whose sister froze to death during a snowstorm. The woman had nowhere to turn for a burial—except to her disgraced state senator, who paid for it out of her campaign account.

Wilkerson smiles. “I can't wait for the Office of Campaign and Political Finance to ask me to explain that one.”