Clifford “Kippy” Richardson speaks at a meeting in 1980. On Feb. 1, the City Council kicked off Black History Month by honoring Richardson, who died in 1994, by naming a meeting room in City Hall after him. Portland Press Herald file photo

Clifford “Kippy” Richardson was always on the move.

As a young boy, he held several jobs as a newspaper carrier, a barbershop cleaner and a shoe-shiner. He was a standout track-and-field athlete at Portland High School in the 1940s. And as an adult, he ran a successful cleaning business with his brother, while being heavily involved in civic groups, whether it was local Little League, track-and-field club, Special Olympics or the Kiwanis club.

In 1971, Richardson became the first Black person elected to a municipal office in Portland, serving two terms on the school committee before being elected to the City Council and then re-elected to the school board.

On Feb. 1, the City Council kicked off Black History Month by honoring Richardson, who died in 1994 at the age of 65, by naming a meeting room in City Hall after him.

His granddaughter, Christina Richardson, said the council action, spearheaded by Councilor Pious Ali, was a “great honor” and years in the making. She said early discussions focused on renaming streets in Libbytown after her grandfather and other notable Black families in Portland. But that effort faltered, after the city’s controversial and unsuccessful effort to rename Franklin Street in honor of the Rev. Martin Luther King Jr.

Christina Richardson, who lives in Portland, said the council’s announcement would have been a source of pride for her grandfather, who was known for his warm smile and connections in the community.

“I couldn’t ask for anything better out of the process, because having a room named in his honor that is used for community is something that my grandfather would have loved and adored,” Richardson said. “My grandfather put in the work for the community. Knowing that the community will be working in this room is so beautiful of a legacy for him.”

The council did not include any resolution or background information during its nomination process. But old newspaper clippings paint a picture of an ambitious, hard-working individual who was not afraid to speak his mind and was undeterred by political setbacks.

City Council candidate Clifford “Kippy” Richardson, 1989.  Portland Press Herald file photo


His personal story is a compelling one. As a boy, he delivered newspapers, before earning 25 cents a week cleaning the floors and mirrors at Ryder’s Barbershop in the West End. He also launched his own shoe-shine business in his free time, at one point earning $18 on a Saturday, which he said was more than his father made. All of this was before he was even in high school.

At Portland High School, Richardson was a standout track-and-field athlete. In 1945, he won the Oliver James Trophy in the South Boston 3-mile marathon, besting a field of 23 runners, including three college athletes. He burned through the course in 15 minutes and 4 seconds despite the rainy conditions. A newspaper described him “an unknown before the race, (who) broke the tape a full 150 yards ahead.”

After high school, Richardson served in the Army from 1950-52 and was a former Golden Gloves boxer. 

He founded Kippy’s Cleaning Service, a commercial cleaning business, with his brother. Their first big account was Grants Department Store, which needed to be cleaned five days a week because a newly installed escalator created so much dust. He helped run the business out of the garage in his Rowe Avenue home for 45 years and at one point employed 23 people. And it was not unusual for him to work 80 hours a week, according to his obituary. Perhaps his most prestigious account was cleaning renowned actress Bette Davis’ home in Cape Elizabeth.

Richardson was named the Maine Minority Small Business Person of the Year in 1984 by the U.S. Small Business Administration.

Clifford “Kippy” Richardson wearing his hat with Olympic pins in 1979.  Portland Press Herald file photo

He was also known for his collection of Olympics pins, which he assembled by trading pins with international athletes over the course of  four Olympic games – in Mexico City, Munich, Rome and Montreal. His pins were all placed on a hat that was said to weigh 3-4 pounds.

Richardson easily won his first political campaign in 1971, earning nearly half of the votes in a nine-way race for the District 3 seat on the school board. News stories said that he was motivated to run because of the inequity among city schools and to bridge the gap between the board and the City Council, which controls school spending. He was a strong proponent of creating the Portland Vocational Technical Center on Allen Avenue, which is now the Portland Arts and Technology High School.

Richardson described himself as a political moderate and a fiscal conservative, who spent years trying to reduce school spending by reducing administrators, while largely protecting teaching positions and sports.

He was unafraid to speak his mind and was occasionally taken to task for it. Shortly after being elected in 1971, he was forced to clarify a comment that some believed suggested that the Clifford School neighborhood was a slum, which he said was not his intent. And he was censured by the school board in 1976, after he surprised his colleagues by unveiling a surprise list of budget reductions at a council hearing.

Richardson was elected to the District 3 council seat later that year. He made headlines when he challenged the city attorney’s ruling that he could not finish the last year of his school board term, while also being a city councilor. He eventually conceded and resigned, later saying that he was exposing a loophole in the city charter that should be closed. During his term he would continue to advocate for school budget reductions, while supporting budget increases for the police and fire departments.

Richardson lost re-election in District 3 in 1980, after an at-large councilor gave up that seat to challenge Richardson. The two were described as political adversaries and Richardson vowed to “whip” his opponent. He would lose two subsequent at-large council races in 1980 and 1982, before being elected to the school board by a 2-to-1 margin in 1986. His political career ended when he sought to return to the District 3 council seat, but was defeated by Tom Allen, a skilled politician who would go on to become a U.S. representative.

Richardson’s older brother, Harold, with whom he owned the family business, was the city’s first Black person elected to public office, when he joined the Portland Water District as a Portland representative in 1963. The regional district is overseen by board members elected by their communities and operates separately from Portland’s municipal government.

At the time, Harold Richardson was only the second Black person in the state elected to a public office. The first was Eugene Butler, who was elected to the Frankfort Select Board in 1949, according to a 2008 report by the University of Southern Maine titled “Diversity at the Ballot Box: Electoral Politics and Maine’s Minority Communities, Post-WWII to the Present.”

Clifford “Kippy” Richardson in 1976.  Portland Press Herald file photo

Councilor Ali said during the council meeting that Richardson was “an extraordinary public servant,” not only because he was the first Black person elected to municipal office, but also because he made the unusual decision to return to the school board after serving on the council.

“It takes someone with courage and a certain kind of caliber of individual to go back to school board after they have been to city council,” said Ali, an immigrant from Ghana who is credited with being the first African-born Muslim elected to public office in Maine. 

Councilor Nicholas Mavodones said he got to know Richardson as he was finishing his time on the school board and Mavodones was beginning his time on the board. He noted Richardson’s busy schedule, which included running his own business and being active in community organizations, while also serving in elected office.

“He was a remarkable man – a kind man. He really cared so much about the city of Portland and the people who lived here,” Mavodones said. “I appreciate you bringing this forward and giving Kippy the recognition he deserves.”

When asked about her grandfather’s greatest accomplishment, Christina Richardson pointed to something that didn’t make headlines. She said her grandfather had been bothered by the fact that seniors at Deering High School were given roses to carry during graduation, but Portland High School seniors were not. He helped change that, she said.

“He was really looking to unify community and make it equitable for all persons,” she said.

Clifford “Kippy” Richardson speaks at a meeting in 1978. Portland Press Herald file photo

Richardson said her grandfather had a tough upbringing and sought to protect his family, so he never really talked about his private or council business, or discuss the challenges or obstacles he faced as the first Black person elected to a municipal office.

“As a Black person with a Black family in Portland, Maine – rising above was always the goal,” she said. “As his granddaughter, I didn’t really hear about the politics or the cleaning business. It was always about staying educated and continuing to move and continuing to make sure your voice is heard and continuing to care for community.”

“My grandfather was just a really caring person – a loving, caring and tough person,” she added with a chuckle. “At the end of the day, he just wanted what was best for the community and I think that as long as we maintain focus on what will ensure an equitable and fair and just community, that would be the ultimate legacy for my grandfather.”

Does that mean the 37-year-old  supervisor at the Portland Public Library is considering following in her grandfather’s footsteps?

“That is a question persons have been asking me for a very long time,” she said. “At this point I’m feeling the waters, but I know my grandfather’s spirit and his fire definitely lives inside of me, so we’ll see where it goes.”

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