Who Is Dianne Wilkerson?

After a stretch in prison, some consulting work, and a recent return to the public eye, the former state senator reaches a critical crossroads.

Photo by Philip Keith / Blouse by Nouvea Fashion

On a chilly fall day, I did my best to keep up with Dianne Wilkerson as she made her way around Boston. First, the two of us, wearing chunky boots, traipsed through an abandoned lot in Roxbury, stepping around an open manhole, large mud puddles, and human excrement alongside developers interested in bidding on the parcel. She explained her plans to convert this wasteland into a community for seniors from Dorchester, Mattapan, and Roxbury. A few hours later, and after an outfit change, she sat at a U-shaped table, behind a paper nameplate, speaking about healthcare inequities. She was among a small group of healthcare advocates and community leaders who had been invited to meet the incoming president of Brigham and Women’s Hospital.

Afterward, as hospital executives and guests made their way to the table of coffee and cookies on the other side of the room, a woman walked up to Wilkerson.

“Dianne Wilkerson,” she said. “Now, I know I recognize your name….”

If the stranger was hoping for a hint, she wasn’t getting one. The two women stood facing each other. An awkward silence ensued.

“Well, it is nice to meet you,” Wilkerson replied cheerily before turning away.

During the few weeks I spent with Wilkerson, I saw versions of this scene unfold as we came across people who recognized her, some who didn’t, and some who thought they just might. Each time, I couldn’t help wondering: What do people think about when they think about Dianne Wilkerson?

Do they envision the accomplished and beloved lawyer and civil rights activist turned eight-term state senator who broke tremendous racial barriers in Massachusetts? Do they remember the woman who commanded respect—and even fear—across the city? Do they recall how she dazzled colleagues with her intelligence, the depth of her analysis, and her unparalleled ability to get shit done? Do they look back on how she never stopped working for her community, during long hours, seven days a week?

Or, do they remember the photo?

You know the one. We all know the one. In it, Wilkerson, a shade younger than now, sports a light-colored sweater set and is seen stuffing $1,000 in cash into her bra. That photo, seared into the memories of Bostonians of a certain generation—and people of any age with curiosity and access to a search engine—has become visual shorthand for a shocking fall from grace, made only more spectacular by the height from which it originated. Wilkerson would go on to resign from the state Senate and plead guilty to taking $23,500 in bribes for using her influence to help someone get a liquor license and in other matters before the legislature. She would spend 30 months in federal prison for her crime.

How people react to Wilkerson, and which version of her they remember, is being put to the test these days more than ever since she was released from prison in 2013. At first, she stayed busy in a fairly low-profile kind of way. She appeared infrequently in the press and kept her head down while working behind the scenes as a consultant on a variety of projects.

That all changed recently. Over the past year or so, Wilkerson is suddenly everywhere you look: helping Black Bostonians get tested and vaccinated for COVID; organizing an (ultimately unsuccessful) effort to rally Black residents behind a single Black candidate for mayor; campaigning to make Boston School Committee members elected—not appointed—officials. She has the ear of the mayor, city councilors, and hospital presidents. She hosts a weekly interview show on Facebook Live, has been appearing in media more often, and decided to open up her schedule to me.

Now, after state Senator Sonia Chang-Díaz announced she is vying for governor, the Senate seat Wilkerson once occupied is coming open again and Wilkerson says she is seriously considering a run. At press time, she said she hadn’t yet made her decision. Still, even the hint of her candidacy has spurred speculative articles, whispers, and entreaties from some urging her to go for it and, among others, concerns that she just might. If Wilkerson does run for political office again, it would mean publicly talking to a whole new generation of Bostonians.

“Do you ever worry that people you meet will go home and Google you?”
I ask her.

“Oh,” she says shrugging, “I assume they will, but there is nothing I can do about it.”

Photo by Philip Keith / Blouse by Nouvea Fashion

On the day that Mayor Michelle Wu was sworn into office, I found Wilkerson waiting for me at a table in Caffè Nero facing a large window that looked out on City Hall Plaza. She slid the program from the ceremony across the table to me. “It was beautiful,” she said of acting Mayor Kim Janey’s and Wu’s speeches.

It was also, she later admits, bittersweet. Wilkerson had led a public and ultimately unsuccessful effort dubbed “Wakanda II” to get Boston’s Black community to rally behind a single candidate: Janey. In the final round of the election, Wakanda supported Wu. “Of course we wished that Kim had won,” Wilkerson says. “But even in the primary, I resolved myself to the idea that it is going to be a long while until we have a Black mayor.”

The irony, sitting there that day with Wilkerson, is that had things gone differently in Wilkerson’s life, Boston could well have already had an elected Black mayor. “There’s a conversation that comes up often when people ask whether we have the potential to elect a Black mayor,” says Michael Curry, the president and CEO of the Massachusetts League of Community Health Centers and the past president of the Boston NAACP. “Who has the gravitas, the respect, to set the table for the first Black mayor? I often say in those conversations that the only person I’ve known in this city that could have done that would have been Dianne. Dianne was a master at mobilizing communities in a way that not a lot of people could have done. She had enough respect across the city that she could have been the one to deliver a mayor sooner.”

When I asked Wilkerson if she agreed with Curry’s assessment, she didn’t flinch. “In 2013, please, yes I could have,” she tells me. At the time of the primary for the mayor’s race that year—and the lead-up to it—however, she was incarcerated and wasn’t even allowed to vote. Bittersweet indeed.

If you go back in time, however, to before her fall, the power she wielded was the stuff of legend. Wilkerson was a trailblazer in the commonwealth. She was the first Black female to be a law clerk in the Massachusetts Appeals Court; the first Black female deputy counsel to the Massachusetts Supreme Judicial Court; the first Black female assistant legal counsel to a Massachusetts governor, under Michael Dukakis; the first Black female partner at a major Boston law firm. But it wasn’t until she was an attorney for the NAACP, and successfully sued the Boston Housing Authority and the U.S. Department of Housing and Urban Development over discrimination in public housing, that she became a household name. She rode that acclaim straight through another barrier and became the first Black woman to be elected to the Massachusetts state Senate. The day she was sworn in and left the law firm, she took a $60,000 pay cut.

Wilkerson brought that same determination to the job of senator. While some legislators spent their time at ribbon cuttings and galas, she worked long hours at the Senate before heading back to her district for a community meeting or to race to the scene of a shooting.

Then there’s her skill set. Curry told me Wilkerson could walk into a meeting with financial professionals, or healthcare professionals, or people from any sector for that matter, and earn their respect and impress them with the depth of her understanding of the issues—their issues. “I have worked in health policy for close to 25 years engaging elected officials at every level and as a civil rights activist even longer, and I can tell you something without any question,” Curry says. “Dianne Wilkerson was one of the most effective elected officials that I have ever met in my lifetime.”

In debates, she ran circles around her opponents. “People were afraid of her,” said a prominent Black Boston businessperson who asked to not be named for fear of criticism. “She was able to understand the issues very quickly and shut up anyone who pushed back on her. Everyone was afraid to have an argument with her in public.” Former state Representative Jeffrey Sánchez recalls being amazed by her intellect, reasoning, and stamina as she conducted a several-hours-long filibuster. “Do you know how hard it is to talk for that long?” he said. “She was grabbing study after study, litigating Black injustices from pre-slavery to that year. Staffers around the building were like, ‘We need to go see this.’ The gallery was filled with young people looking for inspiration.”

Wilkerson was also a woman ahead of her time. She tackled issues such as healthcare inequities, criminal justice reform, and environmental justice long before they became household terms. Still, what she is perhaps best known for as a state senator, as many people told me, was knowing how to drive resources into the most underfunded districts of Boston and to the populations most in need.

When it came to managing her own money, though, she was, by all accounts—including her own—a total disaster. “It’s not my thing, it just isn’t,” she told me. During the early 1990s, Wilkerson failed to file her federal income taxes and was criminally charged with tax evasion for failing to pay $51,000 in taxes. She was sentenced to six months of house arrest at the end of 1997. She came under fire for failing to disclose to the State Ethics Commission consulting fees she’d earned. There were questions about how she spent campaign donations. She owed thousands of dollars in unpaid condo association fees.

Wilkerson insisted people were trying to take her down for facilitating change and for legislating while Black. And she had a point. At the time, she was allegedly the only public official in Massachusetts history to be criminally prosecuted for the not-so-uncommon charge of income tax evasion. As for the consulting income she didn’t report to the ethics commission? Well, the commission had given her explicit permission to provide those services in the first place. Meanwhile, she says, she was withholding her condo payments because of poor service.

After Wilkerson’s first arrest for tax evasion, her constituents, including religious leaders, rallied around her and continued to elect her. In 2008, when she was immortalized in the infamous photo and later charged with taking $23,500 in bribes from undercover FBI agents and an informant, they were shocked and heartbroken. She appealed to the Black clergy, asking them to stand by her once again. This time, they asked her to resign.

Wilkerson’s fall unleashed a complex mix of emotions within her community (a complexity that still persists today). On the one hand, a top leader had landed in disgrace and disappointed many. On the other hand, perhaps the only thing worse was not having her in office any longer. “We lost so much of the voice we had on Beacon Hill,” says state Representative Russell Holmes. “It was such a powerful voice.”

On a Friday night, Wilkerson and I made our way up the stairs of an old Victorian in Roxbury, right off of Blue Hill Avenue. When the door swung open, spilling a warm light onto the dark porch, the house’s proprietor grabbed Wilkerson and held her in a friendly bear hug. We were here to tour a new halfway house for women who have just gotten out of prison. The woman who greeted us had been in and out of prison a few times herself before going to college and founding the place.

After a couple of other guests arrived, we headed upstairs to see the rest of the house. As our small gathering stood on the second-floor landing, admiring the renovated bathroom with the rainfall showerhead, Wilkerson walked up to a picture of a group of women that was hanging on a nearby wall. She moved in close, raised her finger, and pointed to a few of the women, smiling while she said their names as though she were looking at an old family photograph. She was not. It was a photo of inmates at Danbury federal prison in Connecticut, where Wilkerson had been incarcerated. “I did a lot of political work around criminal justice reform, and you think you know what you are talking about, but you don’t,” she says of her time as a senator. “It wasn’t enough for God. He wanted me to see it from the inside.”

A few minutes after looking at the photo, she told the others about some guests on her weekly Facebook Live show, namely City Councilor Julia Mejia and Congresswoman Ayanna Pressley. Very few can pull off a transition like that one—from prison memories to hosting a U.S. representative. Then again, nothing about Wilkerson’s reentry into society has been typical.

In 2013, when Wilkerson was released, her sons drove to Danbury to take her back home. She’d asked them to bring only two things: a change of clothes and a voter registration form. As soon as they crossed the Massachusetts border, she mailed it. Even before the ride was over, she received an offer over the phone for a small consultancy to help someone with a real estate deal. Within a week, she landed a nonprofit job. Friends and well-wishers in her community texted her night and day to check in on her, slipped envelopes of cash under her door, and tucked them into her mailbox to help her out until she was on her feet again. Five months after she left prison, she found herself seated at a table at a ceremony during which government officials were honoring 18 women of color, including Wilkerson, who were changing the world. If that wasn’t enough, then-Mayor Marty Walsh singled her out and referred to her as his “dear friend.”

Not everyone was happy to see Wilkerson, though. Some of the people calling and texting relayed how disappointed they were with her. She says those residents didn’t upset her, and that at least they were better than the people who merely stayed silent. “You know the people when you see them on the street, right? They see you and they turn and go in the other direction. I saw that happen,” Wilkerson tells me. “Or right at the time where you make eye contact, they turn their heads.” When I asked how it had made her feel, she replied, “Their loss” without hesitation.

At the time of her return, some observers believed Wilkerson’s reentry would be more successful if she didn’t feel compelled to be in the limelight and simply worked behind the scenes. With the exception of an unsuccessful run for first vice president of the NAACP, Wilkerson did precisely that: She helped launch a project to aid people with criminal records find work clearing snow and landscaping. She opened a consulting business. She began to draft the plan for the development of the abandoned parcel of city land. She worked on development projects with Black- and women-owned businesses.

Along the way, something happened: Boston’s Black community took note. Her work was uncharacteristically quiet. None of it appeared to be undertaken for political or personal benefit. Then they watched her leap into action when the pandemic started, cofounding the Black Boston COVID-19 Coalition, an organization that raised much of its own funds to do the work the state wasn’t getting done in her community, she says. It soon grew into a large social movement that deserves credit for getting legions of the city’s most vulnerable residents tested and vaccinated. Leaders from other cities and states reached out to Wilkerson to learn how her coalition did it. The president of Brigham and Women’s Hospital has begun collaborating with the coalition.

Holmes said that as people saw the impact of her work, they began to wonder whether benching such a talented leader made any sense. “Dianne would bring it. I mean she would bring it, she would be relentless, a fighter, every single day,” says Holmes of a potential state Senator Wilkerson 2.0.

Wilkerson insists it wasn’t until recently that she began to consider running for her former state Senate seat. Her change of heart, she says, stemmed from her concern about the performance of some of the legislators who represent districts with large populations of Black and brown residents. It was their job, she says, to deliver a fair share of the unprecedented amount of pandemic-era federal resources that the state received. “Black and brown residents were supposed to be the target of these resources, and we got zilch, the crap end of the stick,” says Wilkerson, who regularly pores over hundreds of pages of legislation and budgets with an eagle eye looking for what communities of color are getting. “It is ridiculous. It is the job of our state legislators to get that money to us, and if you can’t do it, then what are you doing there?” Wilkerson insists she doesn’t think she is the only one who can do the job well, but so far, the people who’ve declared or are rumored to be running for the open seat, she says, have proven they cannot.

Just her considering a run has been enough for Wilkerson’s past to become present again. Virginia Morrison, the executive director of the Grove Hall Neighborhood Development Corporation and a Wilkerson ally, says she doesn’t understand why people don’t just move on and focus on all the good that Wilkerson has done and not her arrest and jail time. “I don’t even think it is worth talking about at this juncture,” Morrison tells me. Still, others say that if she wants to run for office and to ask voters for a second chance, she will have to address her past.

As a senator, Dianne Wilkerson dazzled people with her intelligence, her work ethic, and her ability to drive resources to her community. / Photo by Philip Keith / Dress by Diggin Her Roots

If Wilkerson does run, she has a few things in her favor. The first is that a recent redistricting effort added more Black voters to her district. Then there is the fact that the Black community, as Holmes tells me, “believes in second chances.” It is also a community that knows and appreciates, in ways others may not be able to, the unique pressures under which Wilkerson operated as a state senator. “I do not condone what she did,” the prominent Black businessperson told me. “But most successful politicians are part of a successful company or have a partner with money. She was a single mom and was not attached to any business. Her salary wasn’t covering it. Every Black politician works seven days a week and they don’t have a day off. A white legislator can work 9 to 4 and not work on weekends and get away with it. There are so many problems and issues in communities of color.”

Many of those issues, day in and day out, can cause trauma. Not many legislators representing white communities were crafting policy by day and by night helping constituents arrange funerals for their children who’d been gunned down on the streets. And then there was the social context in which Wilkerson was working throughout the 1990s. It was a time, WBZ-TV News political analyst Jon Keller says, when our “political system was one of the most, racist, sexist, old-boy political systems in the United States, and here was a Black woman stirring things up and making a name for herself. You cannot underestimate the pressure she was under, and clearly she handled it imperfectly, to say the least.”

Wilkerson may also benefit from being part of a community that knows the justice system can be skewed and biased. While Wilkerson committed a crime, she was also arguably wronged by the system. Black leaders told me that people instinctively knew she could hardly have been the only one at the State House taking bribes, but the feds went after her. When federal agents came to arrest Wilkerson at her home, officers entered with guns drawn, she says, even though she lived alone with her niece’s daughter. And can you think of anyone else convicted of taking a bribe who had their photo put out there as far and wide as Wilkerson’s?

Not everyone buys it, though. One observer told me that Wilkerson has a “whole Robin Hood story, that she was brought down by some invisible white power elite. She will always be the underdog. She is brilliant in that sense,” the observer says, adding that “she purports this ignorance about who she really is. And it plays.”

Whether race played a role in Wilkerson’s downfall or not, that same observer thinks the current climate around race is benefitting her now that she is making a comeback. Is Wilkerson being given a free pass to forgiveness in a way that someone like Salvatore DiMasi never got, for the simple reason that she is a Black woman at a time when anyone speaking out against her runs the risk of being branded as racist, the observer asked, adding, “Dianne gets a kiss and song and everyone forgives her.”

Clearly, though, not everyone has forgiven her. Some people, in fact, are quite troubled at the idea that she is considering running again. They wonder if putting someone in the State House with her criminal past will reflect badly on the Black community as a whole. They wonder how the single best person for the job could possibly be someone who spent time in prison for crimes related to abusing the very office she may seek to hold again. They wonder if Wilkerson’s time has come and gone, and if she should just stand down and make way for a younger generation of leaders.

One complaint I heard over and over—mostly from people who didn’t want their names revealed for fear of angering Wilkerson—is that Wilkerson has not shown enough remorse, or that “she has no shame in her game,” as Sánchez put it. “I am still waiting to hear a sense of contrition,” says a Roxbury community leader. “That would be the beginning of real healing for me.”

For her part, Wilkerson insists she has apologized. When I asked her the very first time we met if she understood why some people may not be ready to forgive her, she said she did. “Based on what people read and what they were told, I absolutely get why there are some people who would be upset, some people who would be disappointed, and feel like I let them down.”

Wait a minute. Was Wilkerson saying that people didn’t really know what happened? That there was more than met the eye? When I asked her to elaborate, she told me we would have that conversation, but not just yet.

Wilkerson is noticeably self-assured, crystal-clear that her life mission is service, and convincingly at peace with herself.

Wilkerson is sitting across the table from me, against the high back of a sumptuous gray-velvet booth. A warm, soft light filters through beaded chandeliers hanging from the restaurant’s low ceilings. Wilkerson has eaten here more times than she can remember—and one time that few will ever forget. We are at No. 9 Park, the scene of the so-called crime, and the place where the seed for the implosion of her life was planted.

As Wilkerson gingerly gathers a forkful of her salmon, she tells me that until tonight, she hadn’t set foot in this restaurant since that fateful day more than a decade ago when she was photographed here stowing cash in her bra. As we talk, a woman’s voice, drenched in honey, pipes in through the dining room speakers, singing a lounge-y rendition of the Rolling Stones’ “Miss You.” Oooh, baby why you wait so long?

I ask her if being back here brings up upsetting feelings.

“Quite the contrary,” she says. She tells me with an air of nostalgia that what she thinks of when she’s here is not her arrest or the exile from public life that followed, but of all the many meetings she has had at the famous restaurant across the street from the Common. “Far too many moments in this particular venue and on Beacon Hill were moments when good things happened through the work that I was able to do,” she says, adding, “I am not a second-guesser.”

I had noticed that about Wilkerson. She doesn’t spend time looking in the rear-view mirror, wishing things had gone differently. Not even the 30 months she spent in prison elicit a note of regret. She was so rundown, so overworked, thoroughly exhausted, and depressed over the case of a young boy gunned down in front of his home in her district, that she told me she was sure something terrible would have befallen her had she kept on in that fashion. “In some really weird kind of way, it forced me to sit down,” she said. “I would never have sat down if it wasn’t for that happening.”

Wilkerson is noticeably self-assured, crystal-clear that her life mission is service, and convincingly at peace with herself. Still, there had to be things that she would have done differently, right? Surely, if I brought her here, to No. 9 Park, she could think of something, couldn’t she?

I looked over my shoulder at the other diners sipping wine and making small talk, at the colors from the Christmas lights on the Common glowing through the window, and gestured to the room. “Was there nothing that went on in this room that you regret?” I ask. “Is there nothing you would have done differently?”

Wilkerson shakes her head. “I’m trying to go through it and I can’t think of anything I shouldn’t have done,” she says, “because I know so much more about what happened.” Then her voice grows a shade sterner when she tells me that when she took that money that day, she “was working.”

Wilkerson says it takes too long to explain, and everyone thinks they already know the story anyway, but if they really want to learn and have a few hours to spare, she will tell them. It goes something like this:

Wilkerson had been hired as a consultant to help a night club owner named Ron Wilburn—who unbeknownst to her was an FBI informant—obtain a liquor license for a new spot he said he wanted to build in Roxbury. “You can’t bribe me if I am working for you,” Wilkerson tells me. She didn’t sit on the liquor licensing board, she says, and she wasn’t using her position there to rubber-stamp something in exchange for money. Wilkerson tells me legislators were allowed to serve as consultants on business that was not before the legislature. She didn’t hide the money. Quite the contrary, she says, she reported all of her consulting income on her tax returns.

Wilburn’s partner, Manny Soto, had been illegally dealing drugs and soon the feds were involved. Soto was arrested, and Wilkerson figures Wilburn knew that he’d better get Soto out of jail before Soto started to sing. Wilburn struck a deal with the feds: For about $30,000, he’d work as an informant and go after Wilkerson. Wilkerson says she “got traded” and that those in power got what they always wanted—to take her down.

Still, if Wilkerson was in the right all along, why on earth, I asked her, did she plead guilty? She told me she believed she would never be judged by a significant number of Black jurors—who would understand the role that racism played in her arrest—and she would be convicted and go to jail for much longer than if she pleaded guilty. She knew how the system worked, how prosecutors pile on charges to force a plea deal. She couldn’t afford to miss so much time away from her community and her work on its behalf. And, no, she does not regret pleading guilty, either.

There it was. No wonder Wilkerson’s apologies have seemed insufficient to some, her contrition lacking, her demeanor not remorseful enough: “If what I did was wrong,” she tells me, “it was a stretch.”

So why did Wilkerson apologize, as she says she has done, if she doesn’t even believe what she is apologizing for? “Because they believe it, and that is significant,” she said. “I was not going to dismiss that.”

Even now, when people talk to Wilkerson about giving her another chance, she says she feels a small zing in her head and in her heart because she knows the deep-down truth. Still, for now, she is happy to answer questions, but says she doesn’t want to spend her energy clearing her name. She prefers to spend it working to improve her community and, maybe, just maybe, running for an encore in the state Senate. Whether she could pull it off is anyone’s guess, but Sánchez isn’t betting against her. “When Dianne decides to do something, Dianne’s going to put her everything behind it,” he says. “And watch out. She is a moving train.”

Wilkerson told me she’s written some 10 chapters of a book, and that when people one day read it, they will finally have the full story and her name will be cleared. But the book isn’t ready to be shown to anyone. “It’s not the end of the story yet,” she says.

After our meal, we walk into the cold evening air and up the hill a short distance to the State House. Standing in the shadow of the golden dome, she points out to me the window of her old office, which faces the street. Then I see the tail lights flash on a car that is parked right in front of that window. Wilkerson, I notice, is holding a set of keys in her hand. Seconds later she bids me a quick farewell and climbs into that car and pulls away. I stand there stunned. Somehow, she had managed to drive here for dinner and slide into a spot right in front of the window beneath her old office. As if it had been waiting for her all along.