Meet Reuben Harpole, Milwaukee’s Other Mayor

The charismatic, irrepressible Reuben Harpole is one half of a community organizing power couple so influential he’s known as the second mayor of Milwaukee.

Being a community organizer can be a tedious job: conducting community needs surveys, passing out flyers, knocking on doors trying to drum up support or money for causes. Rarely does one rub elbows with celebrities.

But Reuben K. Harpole Jr. is not a typical community organizer.

During some six decades of working on behalf of Milwaukee’s Black community, he and his wife, Mildred, mingled with the likes of Duke Ellington, Lena Horne, Jesse Jackson and even James Brown. Not to mention governors, senators, congresspeople and mayors.

“Back in the 1960s and ’70s, visiting politicians, ministers, artists and musicians couldn’t sleep in the Downtown hotels because of discrimination, so they stayed in people’s homes in our Walnut Street neighborhood,” recalls Harpole, now 87.

If that sounds exciting, consider the perspective of the couple’s children, John and Annette. “When you’re young, it’s kind of a bummer,” says John, now a financial consultant in Los Angeles. “We were tired and want to go to sleep at 8. But our parents said, ‘No, no, you have to meet these folks.’ And we did meet remarkable people and hear remarkable speeches.”

Harpole (left) with Dr. Martin Luther King Jr., early 1960s; Courtesy of Wisconsin Black Historical Society and Museum


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John will never forget the Godfather of Soul. His father was promoting a Brown show, opened by the Chi-Lites, so John was able to board Brown’s private plane at Mitchell Field. John recalls the Learjet being adorned with the pan-African red, black and green color scheme – and a leopard-pattern interior. “I was very impressed,” he recalls. “You have to go forward 50 years to approach that level of cool.”

Annette, who now works in financial services and lives in Racine, remembers lots of babysitters and being latchkey kids. “I didn’t really appreciate my parents’ achievements until I was an adult,” she says. “They did what made them happy and what they thought would make the community a better place.”

The Harpoles have definitely accomplished the latter.

Good Works

Just a few of the many notable initiatives developed by Reuben and Mildred Harpole. 


Freedom Schools

For four days in 1964 and 1965, some 11,000 Milwaukee schoolchildren stayed out of school to protest educational inequality. During the boycott, Mildred helped run Freedom Schools, where parents and clergy became temporary teachers to educate young people about the effects of racism.


Ko-Thi Dance Company

Begun as the Children’s Performing Arts Group in 1969, Ko-Thi preserves, teaches, documents, interprets and performs dance and music rooted in the cultures of the African diaspora.


Community Brainstorming Conference

In the early 2000s, Reuben and Mildred served on the executive committee of this monthly forum in a church basement that worked to educate the Milwaukee community about a range of pressing issues and needs. “All these high-profile indi- viduals –  governors, mayors, aldermen, county supervisors – came to share their platforms,” says Lynda Jackson Conyers, retired publisher of the Milwaukee Times. “That wasn’t available when I was growing up here. You would only see these politicians on TV. During the forum, we had the chance to ask them, ‘What are you going to do for the Black community?’”


Over six decades, the couple played founding and sustaining roles in more than 25 community centers and programs focusing on education, the arts, health care and more. He was so involved in the betterment of the city’s Black community that he is often called “the second mayor of Milwaukee” or “Milwaukee’s Black mayor” – before the city had a Black person holding the office. Mildred, who died in October 2019 at age 84, was always right there with him. She sometimes referred to him as the frontman in their joint effort to create change. The Harpoles have received numerous awards. Reuben has a street named for him (a portion of Second Street near North Avenue), and the Harpole Building stands on North Martin Luther King Jr. Drive, the home of Bader Philanthropies, a charitable powerhouse he worked with for years.

“Reuben, alongside Mildred, has dedicated his life to empowering Milwaukee residents and uplifting our communities,” says U.S. Rep. Gwen Moore, a longtime family friend. “The love and care they poured into Milwaukee will always be remembered.”

James Cameron (left), Marty Stein, Vel Phillips, and Harpole at a Community Brainstorming Conference at America’s Black Holocaust Museum in 1999; Photo by Richard Klatte Prestor

EVEN IN HIS EIGHTH DECADE, Harpole still stands erect, has a firm handshake and often flashes an impish smile. And he readily acknowledges that it was Mildred who pushed his happy-go-lucky younger self into activism.

Reuben and Mildred Harpole at the Kappa Formal at American Serb Hall, 1954; Photo courtesy of Annette Harpole

He grew up on Milwaukee’s North Side, raised by his mother and maternal grandparents after his parents divorced. The two met when Reuben, not long gone from North Division High School, was studying at Milwaukee Area Technical College and Mildred (née Cowan), a Cleveland native, was an undergraduate at Marquette University. “Her diction was so fantastic, it scared me. I was afraid I couldn’t compete with it,” Reuben recalls. “But a voice came to me: ‘You should marry her.’” 

Harpole was drafted into the Army and sent to Korea, where he taught himself the saxophone and joined the band to avoid the battlefield. Mildred graduated from Marquette in 1956, and the two kept in touch while she completed her law degree at Case Western Reserve University Law School.  

After Harpole was discharged, they married in Cleveland in 1959 and then settled down in Milwaukee.

The turning point for the young couple came after the 1967 Milwaukee “race riots” triggered by Black residents’ frustration with housing discrimination and police brutality. The looting, arson and sniping led to four deaths and a state-of-emergency curfew, and subsequent equal housing marches became violent when white residents clashed with Black demonstrators. Mildred told Reuben, who was then selling advertising for the now-defunct Milwaukee Star newspaper, “You’ve got to do something,” to which he replied, “What can I do?”

A Harambee neighborhood cleanup organized by the UW-Extension’s Center for Urban Community Development, mid-1970s; Photo courtesy of The Archives Department, University of Wisconsin-Milwaukee

What he did was consult with his North Side neighbor, former Mayor Frank Zeidler, who put Reuben in touch with a young political science professor at UW-Milwaukee named Belden Paulson. For the next 31 years, Harpole and Paulson developed a variety of programs to address racism and poverty through the Center for Urban Community Development they co-founded under the UW-Extension umbrella. Harpole was a volunteer at first, then held a paid position as senior outreach specialist.

One of the most successful programs the two initiated was to identify and train block leaders, eventually covering some 200 blocks in the central city. These grassroots organizers learned how to talk to their neighbors, identify urgent needs in the community and develop specific requests for government officials.

“Streets started getting plowed, garbage collected, alleys cleaned up,” Harpole recalls. Adds Paulson, “As we walked through the community, Reuben knew everybody. As a white person, I became known pretty well because I was with Reuben.”

A Harambee neighborhood cleanup organized by the UW-Extension’s Center for Urban Community Development, mid-1970s; Photo courtesy of The Archives Department, University of Wisconsin-Milwaukee

Another highly successful program was Summer Prep, a summer boarding school for central city Black males on the campus of Campion High School, a Jesuit boarding prep school in Prairie du Chien. Along with academics, the program fostered self-confidence and ambition.

One successful graduate is David Artis, dean of undergraduate research advancement at the University of California, San Diego. “We had interesting courses like pre-algebra, and then we would do community-building activities, like spelunking,” Artis says. “On Palmer Street, where I came from, we didn’t do a lot of spelunking.”

In 1980, Harpole launched the Rites of Passage course in the Milwaukee Public Schools with his friend and colleague Anthony Mensah. Based on the Akan culture of Mensah’s homeland of Ghana, the course provides a sense of purpose and meaning via guidance through life’s stages, from childhood to adulthood. Mensah used it extensively as an MPS teacher for almost 30 years, and later at UW-Milwaukee. It eventually spread to other cities such as Chicago, Cleveland and Houston.

Reuben Harpole speaking to students at Riverside University High School, where he received an alumni association award, 2016; Photo by Kyle Bursaw, courtesy of University of Wisconsin-Milwaukee

“If it weren’t for Reuben and the program, I wouldn’t be the person I am today,” says ROP elder Heddy Keith, a retired MPS teacher who’s president and CEO of the Center for Leadership of Afrikan Women’s Wellness. Keith says Rites of Passage motivated her to finish her bachelor’s, then get a master’s and today help Black women heal from trauma. “Through
ROP, I learned that my God-given purpose is to be a communal leader, to bring people together to help them reach their goals.”

After Harpole “retired” from UW-Extension in 1997, he kept on working in the Black community, eventually making formal an ongoing relationship he’d established with the Helen Bader Foundation (now Bader Philanthropies). President and CEO Daniel Bader recalls that right after the foundation was launched in 1992, he got a phone call from a guy he didn’t know.

Harpole at his East Side apartment; Photo by Aliza Baran

“It was Reuben, who said, ‘What are you going to do to help the Black community?’” Bader invited him to come in and talk. Reuben would then show up three or four times a month, usually unannounced. “Then people were calling me from all over the city, saying, ‘Reuben gave me your number, told me to call you,’” Bader recalls. “This went on for a couple of years until I finally said, ‘You’re driving me crazy. I might as well hire you.’”

In 1998, Harpole became a program officer at the foundation, where, for the next 10 years, he oversaw the distribution of some 650 grants totaling more than $5.8 million. Among other initiatives, he established its first neighborhood engagement program, the Sankofa Neighborhood Renewal Initiative, that funded business, educational and cultural organizations’ growth in the central city.

One of the more significant Sankofa programs was Homework First, launched in 2000. It promoted academic achievement by encouraging students in third through fifth grades – in partnership with parents, teachers, community members and peers – to develop strong homework skills and habits. The program offered modest incentives, like backpacks and school supplies, to students who consistently handed in their assignments; coaches visited schools monthly to provide support and motivation for all students and to monitor their progress.

Harpole did all of this with three signature qualities that have been the keys to his legacy: an expansive network of contacts built over the decades, an elephant’s memory to keep it all sorted, and a preternaturally positive demeanor. 

He appears, indeed, to know everybody in town. Virgil Cameron, board member of America’s Black Holocaust Museum and son of founder James Cameron, spoke of a time in the mid-1980s when his father was trying to turn a dilapidated building on North Fourth Street into the museum. There was a knock on the door, and there stood Harpole, accompanied by Dan Bader and Marty Stein, another local philanthropist. Cameron recalls, “Dad so impressed them with how much he knew about history – not just African American history but world history, Jewish history – that Dan reached into his pocket, pulled out his checkbook, and gave Daddy a check for $50,000.

And the rest is history – all thanks to Reuben’s introduction.”

Reuben Harpole chats with Reggie Moore, director of violence prevention policy and engagement for the Medical College of Wisconsin, at Sam’s Place Jazz Cafe inside the Harpole Building; Photo by Aliza Baran

Even in retirement, Harpole can rarely go out without running into someone he knows, someone he helped, someone he mentored. Lynda Jackson Conyers, retired publisher of the Milwaukee Times newspaper and a lifelong friend of the Harpoles, had dinner with him last December at Crawdaddy’s in West Allis. On their way out, a young woman in a graduation cap and gown stopped the pair and shouted, “Mr. Harpole! You helped me with my career! I graduated tonight from Alverno! I’ll never, ever forget you!”

“He was thrilled,” Conyers says. “I tease him, ‘You know more people than I do, and I was in the newspaper business.’”

Harpole is also known for his memory. “Reuben has a Rolodex built into his brain,” Cameron says. “You ask him about an individual, and not only can Reuben tell you all about that person, he’ll give you the phone number. How many people can do that?”

And Harpole is always upbeat. “He believes there is good in everyone, potential in everyone,” Bader observes. “His mission is to find that potential and harness it.”

That positivity shines through in spite of the discrimination and hate the Harpoles faced as Black Milwaukeeans working on racial issues – and merely as Black Milwaukeeans. Reuben thinks back to the time, as he and Mildred were about to take communion at St. Elizabeth, another parishioner said to them, “What are you doing here? Why don’t you go to your own church?” John Harpole recalls being kicked out of a park in Shorewood, where the family lived, by the local police because he “didn’t look like a resident.” Annette’s mother told her that the family tried to buy a home in Caledonia but were denied because of their race. Today, Harpole shrugs off these incidents. “Yes, I’ve run into all kinds of situations like that,” he says. “I just ignore that stuff.”

“He believes there is good in everyone, potential in everyone. His mission is to find that potential and harness it.”


WHILE REUBEN WAS BLAZING TRAILS around the city, Mildred was more quietly making her own mark. Together, they were a potent blend of energy and strategy.

“Mildred was quiet, but don’t let that fool you,” says Clayborn Benson, founding director of the Wisconsin Black Historical Society and Museum. “She was brilliant, a heavy hitter. And she had Reuben’s ear.”

As a reading specialist in the Milwaukee Public Schools, she often protested segregation and lack of resources at predominantly Black schools. She later became principal of the Harambee Community School. 

In the early 1970s, Mildred was appointed director of the Milwaukee office of the U.S. Department of Housing and Urban Development, allowing her to pursue her lifelong advocacy of housing equality. “She worked in fair housing in a very hostile environment,” John recalls. “She dealt with a complex regulatory situation with grace, politeness and good manners that masked her fierce intensity. She was one serious lawyer.”

Also in the 1970s, Mildred chaired the Harambee Health Task Force, a community health center that has evolved into Milwaukee Health Services. “Having a health clinic in the community meant that poor people didn’t have to take a bus or cab to the county hospital on Watertown Plank Road,” says Conyers. “They could get quality services right in their neighborhood.” Mildred’s role required her to – despite a lack of any medical expertise – submit a detailed grant proposal to the Robert Wood Johnson Foundation and Fisk University. The application won a $5 million grant – in today’s dollars, the equivalent of $25 million.

Reuben and Mildred Harpole accepting an Educators of the Year award from Education Deans of Greater Milwaukee; Photo by Patricia Kline

The power couple’s strengths were complementary. John describes his father as an “irrepressible” single-point optimist: “It doesn’t matter if the glass is filled to overflowing or only has one drop in it, it is water. Dad will literally look at that drop of water and believe he can fill the glass.”

His mom, meanwhile, was more reserved and strategic. “She could see structures, systemic challenges,” John says. “She provided the infrastructure around which my dad’s energy could be harnessed.”

John remembers that his father would routinely bring someone home for dinner unannounced. One time he brought home a whole busload of people. “Mom just took it in stride,” he chuckles. “She was also incredibly well read and a lot of fun – she was very good at one-liners.”

Adds Annette: “They weren’t demonstrative, but their relationship was clearly one of respect and love. They balanced one another.”

Over the years, organizations as varied as the Archdiocese of Milwaukee, the city government and the Greater Milwaukee Urban League bestowed numerous honors and awards on the Harpoles.

“They’ve won more awards than any of us have ever seen, but they don’t do what they do for the awards,” says Benson. “When they get one, they just put it in the back seat of their car and move on to their next adventure. What matters to them is how they can change lives.”

Carolyn Kott Washburne profiled Julia Taylor in the December 2021 issue. 


This story is part of Milwaukee Magazine‘s March issue.

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