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Dianne Wilkerson steps into new life after prison

Former state senator finds supporters and opportunity

Dianne Wilkerson (second from left) with supporters Willie Mae Allen (left), Mary Tuitt, and Arian Allen.KAYANA SZYMCZAK FOR THE GLOBE

The event honored 18 “women of color changing our world,” but one recipient was singled out for special praise.

Mayor Martin J. Walsh went off script at last Thursday’s event, recognizing his “dear friend” at Table 2. State Representative Gloria Fox described her as a sister in politics and said they had been an “unbeatable team.” And former state representative Willie Mae Allen, just before handing this guest her plaque, said, “We’re depending on you.”

Accepting was former state senator Dianne Wilkerson, once the highest-ranking black woman in state government but recently inmate No. 21757 038, convicted of accepting $23,500 in bribes.


It was the first time many had seen Wilkerson since her release from a federal prison in Danbury, Conn., in September, and it was a homecoming few ex-offenders receive when reentering society. Not only did the Prince Hall Grand Chapter Order of the Eastern Star Jurisdiction of Massachusetts Inc. honor her at the Grove Hall event, but MassEquality will also recognize her among a slew of other champions of gay marriage at an event later this week.

Wilkerson’s reemergence in Boston’s circles of influence seems unexpected for someone whose 16-year political career was pockmarked by controversy and ended in such public disgrace. Her travails included six months of home confinement for tax evasion in the 1990s, followed by 30 days in a halfway house for violating the terms of the sentence. She also paid significant fines for campaign violations on two separate occasions, before her indictment on bribery charges in 2008.

Addressing her conviction for the first time, Wilkerson told the Globe she has been both overwhelmed and humbled by how she has been received since her release.

She said that the arrest came after a particularly trying time in her life but that she takes responsibility for her actions. Wilkerson added that she is offering her story now not as an excuse but an explanation of her state of mind at the time.


“Everything that happened to me, I brought on myself because it was about choices I made,” she said. “Whatever state of mind I was in.”

But last week at Grove Hall, the sins of the past seemed to be forgiven. Those gathered honored her as an advocate and champion who fought for fair housing, safer communities, access to jobs, equitable health care, and same sex marriage.

“If she didn’t care about this community the way she did, we probably would not be this forgiving,” said Cheryl Clyburn Crawford, executive director of MassVOTE and host at the tribute. “Missteps happen.”

Fellow honoree Kelly Chunn said: “She served her time. It’s time to turn the page.”

Wilkerson knows both of her records – the criminal and the legislative – are etched in stone and that she owns them both, saying the irony of how they now intersect is not lost on her. For years, she worked on behalf of men and women with criminal records who needed meaningful support and access to jobs, housing, and education.

With her grandson, CJ Mills, Dianne Wilkerson left an event where she was honored.KAYANA SZYMCZAK FOR THE GLOBE

“Little did I know I would be talking about myself,” the 58-year-old said sitting at her kitchen table for a three-hour interview. “I am now among the legions of what they call ex-offenders, but I am one with a plan.”

Hundreds of people with felony convictions on their criminal records return to the community each month and remain shut out of job, housing, and educational opportunities, she said, resulting in economic stagnation and degradation in the communities they return to.


“We can’t just shut the door and walk away like they don’t exist,” said Wilkerson — an exception, who has landed a job since her release. “I’m going to be a very loud voice.”

Wilkerson entered public life soon after she graduated from Boston College Law School in 1981, while raising two sons on her own. She went on to become a civil rights attorney for the NAACP and in the Dukakis administration. In 1992, she became the first black woman elected to serve in the Massachusetts Senate.

She officially exited in mid-November 2008, the day after her indictment and three weeks after her initial arrest.

Eighteen months later, after initially pleading not guilty, Wilkerson pleaded guilty to eight counts of attempted extortion for taking $23,500 in bribes, including ten $100 bills she stuffed into her bra as the scene was recorded by the FBI.

The eight cash payments, made in 2007 and 2008, came from a witness who was cooperating with the FBI and from undercover agents. The money was to secure a liquor license for a nightclub and legislation to pave the way for a commercial development in Roxbury, which she represented.

During her 30-month prison stay, Wilkerson said, she prayed her criminal conviction would not eclipse her work on behalf of the community.

“I hoped that the mutual relationship could continue,” she said. “I prayed that it would, and my prayers were answered.”


Still, she knows that for every person who forgives her transgressions, “there is someone who sees me and goes the other way. And I live with that.”

There are some things Wilkerson said she remains uncomfortable discussing publicly, declining to explain why she took the money or her reaction to the act being caught on tape and broadcast nationally. But she did say that 2007 was a year of crisis, the year when she began to suffocate under the weight of personal loss and the struggles of the community she represented.

Her father died April 9, 2007. She had gone to visit him the day before, which was Easter Sunday, and says they watched “The Last Temptation of Christ.” He sat in his recliner, wearing a Red Sox hat.

The phone call came at 8:30 the next morning, telling her that he passed away. She arrived at her father’s home in Springfield several hours later. “My dad was still there sitting in the chair where I left him.”

It would be hours before a funeral home came to remove the body, and she said only one employee showed up. Wilkerson said she helped lower her father from his chair to the stretcher, zipped the black bag over his face, and watched as he was driven away.

Several months later, another tragedy struck, this one affecting the community: 13-year-old Steven Odom was slain feet from his Dorchester home after a game of basketball.


For Wilkerson, the death compounded a grief that she said had gone largely unaddressed. “It was almost like walking around on autopilot,” she said.

But she said she felt at the time that she couldn’t be an effective advocate if people also saw her as a victim. “I just kept saying, ‘I’m tired. I’m so tired.’ But I don’t think people really understood,” she said.

After her arrest, she said: “I immediately lost everything. I was in the same position, almost overnight, as many of the people who came to my office for help. I didn’t know how. I didn’t know where.”

All she could do was cry out to God, she said, and he answered.

“People just started coming,” she said. “This is a community, people without deep pockets, who made sure my rent was paid from 2008 until 2011 when I left. This is a community without deep pockets that made sure I had health care. . . . This was a community that would show up at my doorstep with groceries, and say ‘I’ll be back next week.’ ”

Her supporters say that she cared for many of them in their time of need and that the community responded in kind.

“I never thought I would be in a position where I would be on the other side, where I would be the recipient of or need the things that I had done for people for years,” Wilkerson said. “I didn’t do it so they could do it for me.”

Some saw her initial plea of not guilty, her reluctance to resign from office, and her prolonged silence as indifference or possibly arrogance.

“I always marvel at the assessment of my demeanor,” she said. “I had nothing to say because I didn’t know what was going on. . . . I didn’t know what to say.”

And now?

Her focus, she said, is and has been,“How can I make this up? What do I do afterward?”

Prison, she said, forced her to stop and reflect.

“I spent an inordinate amount of time that I was away, that I was imprisoned – and I have to say that I was imprisoned because I don’t want anyone tiptoeing around it – grateful for the time to think,” she said.

In prison, she taught nutrition, exercise, and parenting classes. She worked in the kitchen, serving salad to more than 210 women twice a day, six days a week. “Everyone called me the salad lady.”

She read and wrote, which she said was therapeutic. She completed a book about her life and started another about the women she met in prison.

Wilkerson, who was at a minimum-security prison, said many of her fellow inmates were there for white-collar crimes or were ensnared by mandatory minimum sentencing laws enacted a generation ago amid the crack epidemic. The sentencing disparities between the women and their male codefendants were astounding, she said.

“The overwhelming majority of them were single, heads of households that had minor children. Some didn’t know where their children were. Some were in foster care and disappeared. Some were in bad situations,” she said. “They made it absolutely impossible for me to feel sorry for me.”

Wilkerson was released from prison on Sept. 27. She is no longer a lawyer or an elected official. She is a woman with a felony conviction.

But a week after her release, Wilkerson received a phone call from a former constituent offering her a job. She now is the director of outreach and education at the Academic and Behavioral Clinic, a black-owned mental health clinic. She lives in Roxbury, renting a furnished townhouse.

“I know I am the exception,” she said. “But my being OK, or my family being OK, is not enough for me.”

All ex-offenders need this level of support, she said.

And she said she has begun work to bring improvements to Dorchester and Roxbury, sketching out a plan and having conversations with elected officials and community leaders to make this goal a reality.

“I’m going at this as someone whose status has changed,” she said. “And I’m excited about the opportunity that God has given me to start this new adventure.”

Akilah Johnson can be reached at Follow her on Twitter @akjohnson1922.