The Rehabilitation Of Dianne Wilkerson

On May 17, keynote speaker Dianne Wilkerson addressed the first graduating class of the Black Economic Justice Institute’s Marcus Hall Civic Engagement Academy and pointed to the students to as an example of why Black lives matter.

“The major movers, shakers and organizers of the activity that really blew up after we saw that video of the public execution of George Floyd was born on the backs of young people. That’s who led this," Wilkerson said.

Nineteen graduates nodded in agreement with the former senator, who lost that title 13 years ago when her political career was derailed by scandal and she wound up in jail.

Over the past year, as Boston has battled a pandemic and reverberated with calls for racial justice, Wilkerson has emerged again as one of the city's prominent Black leaders.

Wilkerson has co-led the Black Boston COVID-19 Coalition in demanding equity in testing and vaccine distribution; she is coordinating an effort to rally Black support behind a single Black candidate for Boston mayor; she led voter registration drives in Massachusetts ahead of last November’s presidential election; and she organized a major phone banking operation in December to help national Democrats elect two U.S. Senators from the state of Georgia.

Wilkerson says past scandals could never diminish her activism. “We all have our place, our mission, our purpose and racial justice and social equity has been and continues to be mine," she told GBH News. "And it comes with a whole lot of consequences because inevitably my life's mission being racial equity and social justice means everything I do has to be about and is about race.”

The Arkansas Connection
Wilkerson was born in Arkansas during the Jim Crow era but was raised in Springfield, Mass. Her family history influenced her activism. Her uncles, Albert and Willie Wilkerson, are enshrined in the Arkansas Civil Rights Museum as the first Black men to be tried by Black jurors in the state.

“One Sunday afternoon in the mid-40s, driving down the road, it was, in fact against the law for Black people to drive on the road when white people were driving. You were supposed to drive off to the road and let them pass. They decided that they did not want to drive into a ditch,” said Wilkerson. “They shot at my uncles and one of my uncles shot back.”

A sheriff's deputy and the son of a deputy were killed during the gunfight and her uncles barely escaped an attempted lynching. With the help of Black friends and a local attorney, the Wilkerson brothers fled to Little Rock, where the two Black men were later convicted by a jury of their peers. After serving their sentences, Albert moved to California and Willie to Massachusetts, where his family followed. Dianne Wilkerson says her activism connects directly to her uncles’ refusal to abide by the rules of Jim Crow.

Wilkerson graduated from Boston College Law School in 1981. Toward the end of the decade she brought a discrimination lawsuit against the Boston Housing Authority, that made her a household name, but also made her the target of death threats.

Meredith Nierman GBH News

Wilkerson said threats came with the territory. "I pissed a lot of people off because that's the mission I chose."

In 1993, Wilkerson dislodged long-time Black state senator Bill Owens from his job, becoming the first African American female to serve in the Massachusetts Senate. She gained a reputation for taking on the powerful police unions and representing the interests of Black, Latino and LGBTQ communities. But she also ran into trouble for evading taxes and misusing campaign donations.

Charges Of Corruption
Four years after being elected, WIlkerson was sentenced to house arrest after pleading guilty to failing to pay $51,000 in federal income taxes. WIlkerson described the prosecution as "selective." Her argument was given credence by a 2015 Boston Magazine story authored by a Wilkerson critic who wrote that it 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."

But then came October 28, 2008 — the day Wilkerson describes as the lowest point in her life — with her arrest by the FBI. She had been filmed by agents stuffing ten $100 bills into her bra inside a restaraunt while meeting with a business contact who turned out to be a confidential informant. The money was supposed to guarentee legislation sponsored by Wilkerson that would have allowed the businessman to build a nightclub in Roxbury. Altogether, prosecutors alleged, Wilkerson received $23,500 in bribes.

In 2010, Wilkerson pleaded guilty to eight counts of attempted extortion. But today she insists that she was set up by the feds.

“There's absolutely no question that that's what happened. The feds never denied it.”

But does she regret her own actions?

“I would say yes,” said Wilkerson. “But I don't know what I could have done, like I did not expect [the informant] to bring cash and I couldn't walk down the street with it in my fist. It was out of caution as opposed to subterfuge. Like, I didn't even have an envelope.”

The stunning rise and fall of the state’s only Black senator had a profound impact on politics, said former Democratic Lt. Governor Evelyn Murphy. “I just remember seeing it in the newspapers," she told GBH News. "And she's so bright intellectually. She's one of the smartest women I've seen in the legislature at the time. So, I was overcome by the loss of such talent and such a leader.”

Murphy added that Wilkerson has paid her dues and that her leadership is needed now more than ever.

On the day she arrived at the Federal Correctional Institution in Danbury, Conn., Wilkerson says she gasped at the prospect of serving three and a half years. She was housed with non-violent offenders in a camp, but it was still prison.
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“No bars, no rooms, no doors, no locks, but make no mistake about it, your freedom is impinged. That's the piece that you can't get around.”

Wilkerson dished out salads in the cafeteria, washed clothes in the laundry room and taught history to older female inmates.

Dianne Wilkerson Comes Back
She was released in September of 2013, and the rehabilitation of her image began almost immediately with Boston Mayor Tom Menino the next year presenting her an award as one of 18 "women of color changing our world."

Eight years out of prison, many people across color lines seem to have accepted Wilkerson back into the fold — which Boston PR professional Colette Phillips, a longtime friend and ally, says is deserved.

“Dianne deserves to have her image rehabilitated. She has demonstrated since she has come back that she is committed to equity, social justice, all the things she was always committed to," Phillips said. "No one did a better job of that [fighting for social justice] than Diane Wilkerson when she was an elected official, and she continues to do so.”

Lisa H. Thurau, a former attorney with the Juvenile Justice Center at Suffolk Law School said Wilkerson was “a model of fearlessness” and really “pushed the envelope” in protecting minority teenagers who were disproportionately stopped and frisked by police on the streets. Thurau, who now heads up the nonprofit, Strategies for Youth, said she has never forgotten the role Wilkerson played in “advocating for the city’s most marginalized residents” and welcomes her return to the public arena.

Some of Wilkerson’s fiercest critics in the past chose not to comment for this story. Calls to Jim Lyons, head of the Massachusetts Republican Party, went unanswered. Another former critic in one of Boston’s Black communities, Kevin Peterson, has had a change of heart on how he views Wilkerson. In 2015, Peterson — head of the New Democracy Coalition — penned an op-ed for the Boston Herald stating that Wilkerson was “angling for a way back into community life," citing the infamous photo of her stuffing money into her clothing.

Peterson now says he applauds the work Wilkerson has done over the years to make sure Black lives matter and put that image behind her.

“Those optics will always be with her," he told GBH News. "They'll always be in the minds of people who follow politics in the Black community. That's unfortunate because we all should afford each other second chances and second opportunities.”

Wilkerson says she will never again risk the trust of her community and those who depend on her to fight on their behalf.

“I'm so very, very, very committed and careful not to do anything else, ever to rattle that respect or trust again," she said. "It's not that I get up saying, 'Well, I wonder what I can do to regain it,' because I feel like there's nothing else I have to offer but what I'm doing right now. And I'm satisfied with that.”