Why It’s Hard to Feel Sympathy for the Man Being Called Oprah’s ‘Secret Son’ (But You Should)
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A man dubbed “Oprah’s secret son” is getting an epic cold shoulder from the media mogul.

My first instinct upon hearing the story of Calvin Mitchell—a Chicago man Oprah had helped as teenager—was join the club, buddy – we all want to be Oprah’s child, or at least a family member. I, too, have shared a moment with the Big O that I will cherish forever. After our brief encounter I wished she could have said, “Hey Yolanda, how about I take you under my wing and teach all the ropes of the media?” Or something, anything, that would seal our fate as woman and fairy godmother. That’s the Oprah effect: in two minutes she can make you feel like you’re the smartest, most amazing person in the world.

But I digress. [Feel free to insert your Oprah wish here.]

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Last month, before her appearance on The Late Show with Stephen Colbert, the National Enquirer orchestrated an Oprah “ambush” where Mitchell would try to get a word with her. In a series of photos, he can be seen talking to the media mogul. She acknowledges him and says a few words. But you can tell she’s not having any of it.  

This week, in an interview with Entertainment Tonight, Oprah says she met Mitchell over 20 years ago when she was filming the TV movie There Are No Children Here.

“We were shooting in the projects in Chicago and I was sitting on set during a break, and this cute little sparkly-eyed boy came underneath the yellow tape to hand me a soda,” she said. “I was so charmed by him that I started talking to him about his family, his school life, and found out that he was in a situation where his mother didn’t have a job and they were stuck in the projects.”

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Oprah then enrolled Mitchell in a private school and helped his mother find a job. The family moved out of the projects, but Mitchell just couldn’t get himself out of bed to get to school on time. He was eventually expelled from school.

“I had a long conversation with him about how disappointed I was but I was going to give him another chance,” Oprah said. “I found a school in Mississippi that was a private boarding school because I thought if I could remove him from the environment that he’d been accustomed to growing up in, that maybe that would be helpful to him.”

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It didn’t work. Mitchell decided he didn’t want to stay at the boarding school because he wanted to be with his family in Chicago.

“I said, ‘Calvin, this is the moment. This is a seminal moment for you. I know you are 16 and can’t see the road ahead, but if you leave this school and refuse to get an education,” she said. “I have tried to offer you an education twice—there isn’t another school I can put you in. If you leave this school, I am done. There is nothing else I can do.’ … And that was my last conversation with Calvin in the early ’90s.”

The next time they met was outside The Late Show earlier this month where Oprah says she asked a member of her team to get Mitchell’s number. That is, until she found out he had sold his story to The National Enquirer. Insert a bruh, how could you?

“When I realized the whole thing was a setup, I was no longer interested in speaking to him,” said Oprah, adding that she wasn’t hurt by his actions, but “disappointed.”

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In an interview with The Daily Mail, Mitchell says he is remorseful about letting Oprah down. “I want to talk to her because we never got a chance to say goodbye,” he said.

It’s easy to cast Mitchell as ungrateful and downright foolish. But let’s consider for a moment his upbringing and surroundings. In his interview, Mitchell recalls his family being supportive of his desire to leave the Mississippi boarding school to get back home to Chicago.

“I didn’t have anybody in my life to saying ‘stay there, get your education,’” he said. “My mother… ‘come home baby, we miss you.’ My brother… ‘we up here partying, man.’

With that kind of reaction from his family, there was little chance for Mitchell’s success. I’m not making excuses for his behavior, just reminding us that we’ve heard this story before: Young child is plucked from a low-income neighborhood and placed in an elite school but can’t cope with a world that is culturally unfamiliar. 

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In the 2013 documentary, American Promise, filmmakers Joe Brewster and Michèle Stephenson follow their son and his best friend’s journey—from kindergarten through high school graduation—at the elite Dalton School. In the beginning the parents are excited and hopeful about the opportunities an elite education will afford, but as they get older it becomes apparent the boys are not coping as well as they could. One of the boys leaves private school to attend a public school.

“We understood that this was a school that the ‘1 percent’ sent their children to,” Stephenson told The Atlantic, “but not having grown up in that environment, neither of us understood the extent to which the social and emotional sides of our child’s development would be at stake.” 

I can think of many classmates at my upstate New York boarding school who fit Mitchell’s profile: smart, from the city and coming upstate to boarding school for a fresh start because of programs like Prep for Prep or A Better Chance, or they were great at sports (basketball was a favorite). But life outside the familiar could be hard. Our school was something like one percent Black, and of that most of us were Black girls. I can count the number of Black male classmates who stayed longer than two years on one hand. Many returned to city public schools to continue their education.

Mine was a happy ending academically, but questionable in terms of cultural pride and self-esteem.
We don’t know all the specifics here, but we can say Calvin Mitchell has had to learn from his mistake, and from the looks of it, life has been hard. He deserves a reprimanding (he blew it!), and some compassion.

But Oprah owes him nothing. She never did.

Yolanda Sangweni is the entertainment editor at ESSENCE.com. Follow her on Twitter.