I try to read the city’s major newspapers daily. But a June headline in the Boston Herald stood out. It was the Joe Battenfeld story on Dianne Wilkerson. The headline said, “Felony conviction isn’t holding her back.” As if something that happened is 2010 should.
The disconnect is this: why would Wilkerson’s conviction prevent her from speaking her mind?
I took some time to look, but I could not find a single Boston Herald writer who began a story by identifying the president as a convicted felon. Yet when it comes to Dianne Wilkerson, her conviction becomes the headline frame.
The Herald and the mayor’s office may want to discredit her, and they may not understand why so many people not only listen to her but follow her. The explanation is not that complicated. The Black community has not forgotten who Dianne Wilkerson was before her conviction. She made history as one of the first Black women to make partner at a major Boston law firm. She became the first Black woman elected to the Massachusetts Senate. She passed major legislation that helped the Black community. That history did not disappear because of her conviction.
Dianne has tried to organize the Black vote for every major campaign. She along with Richard Taylor held a series of meetings with Black leaders, which led to a town hall, on increasing the accountability of our public officials. She’s working with Mac Hudson and others on a Black agenda for Boston. She recently gave a TED Talk at a Roxbury site. Although not in office she still deals with constituent issues. She has an amazing Rolodex built from her years of service. Dianne has earned the right to be heard. That’s why many in the community listen to and support her.
When Dianne Wilkerson ran for her old state Senate seat in 2022, she finished third but still received 4,388 votes — more than the number of votes cast for the winning District 7 city councilor in both 2023 and 2025. In 2023, her 4,388 votes were also almost as many as District 4 Councilor Brian Worrell’s 4,665 votes. That is not the result of someone no one listens to. Chuck Turner also had a CORI, but that did not stop the overflowing support he received from the community at his funeral. The Black community has a long memory. It remembers service as well as failure, contribution as well as conviction.
Wilkerson is also an avid micro-blogger on Facebook and a podcaster through Woke Women Wednesdays and her other platforms.
She has her finger on the pulse of the community. Although she is out of office in the formal sense, in the eyes of many people she still represents the community by giving voice to their issues.
The Herald writer and the mayor’s office also seem to forget how many people in the Black community have some type of CORI. That is why the Wilkerson case highlights the hypocrisy that many Black returning citizens face. Like Dianne, many have served their sentence to society. But the media is slow to forget — unless you are rich, powerful, white and politically connected.
And lest we forget, President Trump was convicted in New York state court on 34 felony counts of falsifying business records in the first degree. He faced 91 criminal counts across four indictments and cases: the New York hush-money/business records case, the federal classified-documents case, the federal election-interference case and the Georgia election-interference case. A civil jury also found him liable for sexual abuse and defamation against E. Jean Carroll. Judge Lewis Kaplan later wrote that the jury’s finding amounted to rape in the common modern understanding of the word, even though New York’s then-legal definition was narrower.
Yet I have not seen the Boston Herald begin its stories about Trump by calling him a convicted felon. I have not seen every story about his presidency begin with a reminder of his convictions, indictments, or civil liability. For Trump, the office comes first and the record comes later, if at all. For Dianne Wilkerson, the record comes first.
That is the double standard. It is also why what Bryan Stevenson said becomes painfully true: in this country, it is better to be rich and guilty than poor and innocent.
And this is where the story becomes larger than Dianne Wilkerson.
If a criminal record does not automatically disqualify a man from holding the nuclear codes, commanding the military and representing the United States before the world, then we need to stop pretending it should automatically disqualify everyone else from earning a paycheck, renting an apartment, rebuilding a reputation or participating in public life.
For ordinary people, especially poor people and people of color, a criminal record can become a life sentence. It follows them into job interviews, housing applications, professional licensing, college admissions, public benefits and civic life. A person may serve their time, complete probation, rebuild their life and still be forced to explain the worst thing they ever did every time they try to move forward.
Why should a CORI or prior criminal conviction prevent someone from working at Dunkin’ but not prevent someone from being president of the United States?
If a felony conviction does not automatically disqualify a person from holding the highest office in the country, then it should not automatically disqualify millions of others from ordinary life.
If Trump can be president, returning citizens should be able to get a job.
They should be able to rent an apartment.
They should be able to go back to school.
They should be able to vote.
They should be able to serve, lead, work, worship, parent, volunteer and rebuild a name not permanently reduced to a record.
Either America believes in second chances, or it does not. But we cannot keep offering redemption to the powerful while denying opportunity to everyone else.
Ed Gaskin is the Greater Grove Hall Main Streets executive director and a graduate of MIT’s Sloan School of Management.
