Jim Rooney grew up a poor white Southie kid in the ’60’s, and ’70’s, in a Boston that was bitterly divided — economically, ethnically, racially. It was Charlestown versus West Roxbury; African-American versus Haitian versus Asian versus white, he recalled.

“We had hurtful names for every group we could think of, and we were taught stereotypes about each other that were wrong and dangerous,” Rooney told a packed house at the Cutler Majestic Theatre Saturday morning as he opened the first in a series of citywide conversations on race, convened by Mayor Martin J. Walsh.

The extraordinary session was marked by frank and emotional remarks, intense at times but also civil. Such self-examination is essential, Rooney said, for the racism of his childhood is not confined to history. If left unacknowledged, he said, it is a poison that will sicken the city.


“As a city, we are hanging on to a whole lot of messed-up crap,” said Rooney, president and chief executive officer of the Greater Boston Chamber of Commerce. “It’s time to get it out, and have the uncomfortable conversations.”

Kendra Gerald, a biracial 16-year-old Roxbury girl, spoke of the pain she felt when confronted by those old hatreds — when her classmates told her black people steal, or that their parents would disown them if they dated a black person.

“Is this what the general white population thinks about me and other people of color?” she asked.

Saturday’s talk launched a series of citywide events that will span the coming year. Walsh began planning the series while he was still campaigning for mayor in 2013, after a woman in Jamaica Plain pressed him on whether he thought Boston was a racist city. Attendees left saying they were pleasantly surprised by the honesty with which the subject of white privilege was handled, with white speakers openly admitting their failures in order to learn from them.


Ruth Georges, a 31, who is Haitian, lauded what she called a show of “strong leadership” by the city.

People were “speaking to communities that are being oppressed by societal structures, and speaking to those who don’t understand that they are part of those structures,” said Georges.

Saturday’s event was in the works long before President-elect Donald Trump even announced his candidacy, but Walsh said the timing — less than two weeks after a fractious election that has inspired protests — was fitting.

“This is a time when our nation is in great transition,” Walsh said. “We have no idea where the [leadership] is going to take us. But we are not going to go backward. We are going to go forward.”

Speakers hailed from many fields: academics, city officials, an author, and two young people of color who spoke about the weight the country’s history of racism brings to bear in their daily lives.

Dr. Monica O'Neal, a licensed clinical psychologist, spoke at the session.
Dr. Monica O'Neal, a licensed clinical psychologist, spoke at the session.Jonathan Wiggs /GlobeStaff

“From an early age, I learned to be afraid to be black,” said 20-year-old Dante Omorogbe. His grandparents told him stories about the deep South, where whites terrorized black people for fun. In Boston, Omorogbe gets stopped by police when he’s walking down the street, he said, whether he’s wearing a hoodie, or a button-down shirt and khakis on his way to an interview.

“From the murder of Emmett Till, to the murder of Trayvon Martin — two boys who looked like me, and did nothing wrong . . . racism isn’t just a word,” Omorogbe said.


Debby Irving, who wrote the book “Waking Up White,” spoke of the mistakes she made in trying to understand racism and her slow realization that she had internalized stereotypes about white superiority. She flashed images on the screen behind her: the smiling white faces of the cast of ‘Friends,’ the white faces of our first 43 presidents. Whites are kind, whites are leaders, whites are Americans — she had been blind to these stereotypes, she said.

She spoke of learning about “redlining,” the systematic process of keeping black people from moving into “white” neighborhoods that today still shapes our racially and economically segregated cities — and how that realization shook her faith in the myth of America as a great meritocracy, where everyone gets what they deserve.

“White skin carries history,” she said.

Walsh shared a conversation he had with one of his staffers about learning to drive. The staffer, a person of color, was teaching his son that if he was pulled over by police, he should put his wallet on the dashboard, and say “Yes sir” and “No sir.”

When Walsh was growing up, he said, his first move upon being pulled over was trying to think of friends he had in the police department whose names he could drop. If that failed, he said, he’d try to think of family members the officer might know.

“The point of it is, those experiences are very, very different,” Walsh said.


During a question-and-answer period in which attendees spoke to Walsh, Dr. Monica O’Neal, a Harvard-trained licensed clinical psychologist and Harvard Medical School lecturer, questioned officials’ emphasis on the need to talk about race without hostility. Officials had called for conversation without anger or defensiveness.

“That seems a bit unfair,” she said. Race and racism rightly raise strong feelings, she said, and banning the expression of those feelings “feels a bit like limiting the truth of what needs to be heard.”

O’Neal pressed him to say flatly that racism is a problem in the city, which Walsh did, saying, “Boston has an issue with racism.”

Other attendees voiced fear of police, or spoke of their desire for more “pipelines to equity.” One woman lamented the fact that some people in the city simply would not attend talks like these on race, and so would not be reached.

The crowd at the Cutler Majestic Theatre in Boston on Saturday.
The crowd at the Cutler Majestic Theatre in Boston on Saturday.Jonathan Wiggs/GlobeStaff/Globe Staff

Some of the attendees and many of the speakers touched on the election of Trump, and urged people to fight to protect the rights of all Americans by doing things such as speaking openly about race in gatherings such as this one.

“It seems incomprehensible that this country would follow seven years of the first African-American president with someone who uses racism, xenophobia, and sexism to become president,” said Ceasar McDowell, professor of the Practice of Community Development at Massachusetts Institute of Technology. “When I hear people protesting, speaking up to protect those who are scared, I know there’s an America that wants to be.”


The United States, he said, contains the most complex group of people who have ever lived together. And while conversations about race often take place within groups of people who feel the same way, it is a rare thing for people with differing views to gather and speak openly and honestly.

“We can use our conversation around race,” he said, “as the anchor for a new democracy.”

Morgan Shattuck at the race dialogue session on Saturday.
Morgan Shattuck at the race dialogue session on Saturday.Jonathan Wiggs /GlobeStaff/Globe Staff

Globe correspondent Martha Schick and Meghan E. Irons of the Globe staff contributed to this report. Evan Allen can be reached at evan.allen@globe.
. Follow her on Twitter @evanmallen.