One evening in 1982, 12-year-old Rasheda Ali settled into her seat beneath one of the massive, dazzling chandeliers inside Chicago's Drury Lane Theatre. Rasheda, her twin sister, and her other two siblings were in for a special treat. It was opening night of the four-week run of Neil Simon's Come Blow Your Horn, and the kids had front-row seats. An excited Rasheda squealed when she saw her mom strut onstage as Connie Dayton, the love interest of the play's main character, Buddy Baker, who was played by Demond Wilson (Lamont from TV's Sanford & Son). "It was such a magical experience," Rasheda, now 40, says of the performance. "To see my mom onstage was the most amazing thing. It was just so cool to see her succeed."

After her parents divorced, Rasheda, her sisters, and her brother went to live with Khalilah's parents in a seven-bedroom mansion in a small Chicago suburb. Khalilah had purchased it after selling the home she owned with Ali in 1978. By then, the champ had relocated to Los Angeles and married Porsche. Khalilah left the kids behind and took off for L.A. to pursue an acting career. She says Ali's divorce payments covered her living expenses and allowed her to travel around the country for speaking engagements and leisure. Khalilah also had a side gig selling photographs and paintings of famous people she met, which she claims netted her $300,000 from 1978 to 1982, the time she spent trying to make it in Hollywood.

She didn't get far. Khalilah had a small role in The China Syndrome. She met and befriended the film's marquee actors, Jane Fonda and Michael Douglas, on the set of the Oscar-nominated film. She says she also made appearances on The Jacksons, a variety show featuring Michael Jackson and his siblings.

Khalilah reads to Gianni Martinez from her children's coloring book, Old Fashioned Values and Good Manners, Coloring to Learn.
Photo by Bill Wisser /
Khalilah reads to Gianni Martinez from her children's coloring book, Old Fashioned Values and Good Manners, Coloring to Learn.
Khalilah gets her hand wrapped by Jolie Glassman of South Florida Boxing Gym in Miami Beach, where she trains to stay in shape.
Photo by Bill Wisser /
Khalilah gets her hand wrapped by Jolie Glassman of South Florida Boxing Gym in Miami Beach, where she trains to stay in shape.

"Personally, I felt an emptiness," Rasheda says. "I wanted desperately to live with my parents, so it was frustrating for me. But whatever resentment, I didn't show it. She was going through some hardships too."

By the mid-'80s, Khalilah returned to Chicago, where she remarried and was divorced three times. Khalilah was also finding herself frequently in court. According to records in Chicago, she was a plaintiff or defendant in ten lawsuits between 1986 and 2007. Insurance companies, banks, and the Illinois Department of Revenue won judgments against her for more than $56,000, and she sold her mansion. She declined to speak in detail about her litigation. "I just leave that stuff alone," she says. "I just don't discuss it."

A warm breeze cuts through the parking lot of a white, two-story apartment building with faded aqua trim at 85th Street and Harding Avenue in Miami Beach. Khalilah sits on a tan leather recliner in the one-bedroom unit of her neighbor, Jose, a middle-aged Hispanic man with receding black hair. Every morning, Khalilah visits Jose for a cup of coffee before catching the bus for work. "Jose has become a dear friend," she says. "He loves to entertain me and my other neighbor, Geneva."

Dressed in her work uniform, she caresses the head of the cane that Mobutu Sese Seko gave her 27 years ago. Khalilah claims she has made millions of dollars since divorcing Ali. But she declines to get into specifics about her finances. After selling her mansion in 2001, Khalilah says, she bounced between California and Illinois trying to figure out what to do with herself. "I want to get back into acting," she says. "I'd like to do commercials."

Khalilah moved to Miami in late 2008, settling into an apartment off NW Seventh Avenue and 58th Street. She found a job at the University of Miami Hospital and lasted two and half years before she was laid off. Last November, after relocating to North Beach, she was hired at Mount Sinai. Khalilah trains two days a week at the South Florida Boxing gym and goes to South Beach nightclubs to pass the time.

She insists she is not destitute. "I have a hidden trust," Khalilah says. "I spend my money wisely. Whatever I can't cover with my paycheck, I can dip into my trust."

She says she is renting her drab apartment while she shops for property in Miami Beach. She's being picky too. "I went to see a two-bedroom condo with no view the other day, and the woman wanted $275,000 for it," Khalilah says. "I asked her if she was out of her damned mind."

Khalilah puts down the cane and grabs her laptop. She opens a folder containing dozens of photographs and clicks through the images. There is one of Ali, with boxing promoter Don King, in his younger days in Africa. There are several pictures of her and Ali when she began dating him, including a shot in which a beaming Khalilah sits on the champ's lap.

She shows off photos of herself and her four children inside their opulent Chicago mansion as well as pics of her with celebrities she has met over the years, from those who have died, such as Sammy Davis Jr. and Teena Marie, to those who are still here, like P. Diddy and Jon Secada. Khalilah clicks on a folder of pictures from her daughter (Rasheda's twin) Jamillah's wedding in Naples last year. One of the photos shows Khalilah, wearing a spring dress and large matching hat, cheek-to-cheek with Ali. They are both smiling. "No matter what, we will always be friends," she says. "He was my first boyfriend. I was a virgin when we got married. He showed me what it was to be a strong woman."

Khalilah shuts down her computer and places it in a black book bag that she slings over her shoulder. She shuffles out of the room, humming a familiar refrain. "Ali-boom-bye-yae," she purrs. "Ali-boom-bye-yae."

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