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  • May 11, 2025

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860 WNOV Exclusive: Co. Supervisor Rainey Fulfills Promise to Late Philanthropist Rosenberg

July 4, 2015

By Ariele Vaccaro

Milwaukee Co. Supervisor Khalif Rainey pictured here.

Milwaukee Co. Supervisor Khalif Rainey pictured here.

As a teenager attending Riverside High School, Khalif Rainey didn’t see a whole lot in himself.

He transferred from school to school and didn’t get exceptional grades.

He faced adversity at home in the form of drug addiction and gun-violence against his own mother.

Late Milwaukee philanthropist Jack Rosenberg seemed to see the future of his city in the young Rainey, however.

He met up with the teen at a local Baker’s Square restaurant to talk.

“He would just try to figure out what could he do,” for the city, said Rainey.

Rosenberg cared deeply for the African American community in Milwaukee.

According to Rainey, the Jewish philanthropist’s love of jazz music helped him to connect.

“He thought it was just beautiful, and the people that created it were just beautiful,” Rainey said.

When Rainey graduated from high school, Rosenberg granted him a $20,000 scholarship to attend college.

However, the gift came with one condition. Rainey would have to come back to serve his community after receiving his degree and use the knowledge he gained to better the lives of his fellow Milwaukee residents.

Rainey did go off to college. He graduated from Southern University and A&M College in Baton Rouge, La. with a bachelor’s degree in political science.

Then, he came back to fulfill the promise he made to Rosenberg.

Soon after returning, he saw that his former high school teacher Ashanti Hamilton had become a city alderman.

It was with Alderman Hamilton that Rainey was able to get his foot in the door of Milwaukee politics.

The young college graduate interned in Hamilton’s office.

Rainey then moved on to work as a legislative assistant under U.S. Representative Gwen Moore.

For a decade, he handled education, housing, consumer concerns, and a number of other matters that he oversees today.

The idea of running for office himself didn’t come up for a while.

When it did, he was working under current State Senator Nikiya Harris Dodd. In a grocery store, he broke it to Harris Dodd that he was considering a campaign for office at county supervisor.

“She kind of laughed, gave me a sly smile, and said ‘Let’s do it,’” recalled Rainey.

On April 2, 2013, Rainey won the Milwaukee District 2 County Supervisor seat. He’s been serving there since, always with Rosenberg’s hopes for him in mind.

“I try to live up to that prerequisite,” said Rainey. Rosenberg passed in 2005. Rainey still speaks to his wife, Lucy, regularly.

Much of Rainey’s focus during his tenure as a county supervisor has been on expanding voting rights.

In March, he urged Wisconsin legislature to allow 16-year-old students to vote in their school board elections with a resolution to amend the state constitution.

He’s made efforts to allow teens to pre-register to vote at the Department of Motor Vehicles, when they receive their driver’s license.

He’s pushed for a living wage for Milwaukeeans.

Over the course of his two years in office, he’s allocated about $1 million dollars toward McGovern Park.

“I’m really trying to make it the crown jewel of the north side,” said Rainey.

Recently, he’s erected a new “Chess in the Park” summer program for Milwaukee youth.

But while county parks grow bright, some in Milwaukee experience the city’s darker side.

Rainey, now 34, lives in District 2 with his wife Manandra and their 10- month-old daughter Ayah Belle.

“I never imagined loving anything or anyone so much,” said Rainey of his daughter.

It was in his home district, on 58th St. and Fairmount Ave. that 5-year-old Laylah Petersen was shot and killed last November.

”I can’t even fathom — I can’t even imagine the pain and agony that family went through,” said Rainey.

He wishes for Ayah to live in a thriving Milwaukee where she doesn’t have to fear gun violence, where she has opportunities for success, and where she can enjoy the city she lives through recreation that brings out the best in the community.

As Rainey looks forward, he sees the Bucks arena as a way to make Milwaukee that city.

He argues that Milwaukee has lost a number of valuable assets over decades, like manufacturers and breweries that once dotted the metropolis, and that the Bucks arena can help replenish them.

As the arena continues to gain support from city and state officials, it could soon be that Rainey sees the Milwaukee he envisions.

Co. Supervisor Khalif Rainey spoke to Eric Von during The Eric Von Show which airs Monday through Friday from 7:00 a.m. to 9:00 a.m. on WNOV 860 AM The Voice.

Listen to WNOV on TUNE IN on your mobile device or online at WNOV 860.com.

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Popular Interests In This Article: Ariele Vaccaro, Jack Rosenberg, Khalif Rainey, Philanthropy

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