Being Oprah’s Cousin

January 13, 2024
11 mins read

Kenneth Winfrey Reports

Friday, June 8, 2007.
By Kenneth Winfrey
When people hear my last name, there is an obvious question that comes to mind, and I get asked all the time. From the customer service representatives on the phone to the mailman. From the lady at the grocery store looking at my debit card to the people at the doctor’s office.
From my nosiest (but sweet) neighbour to the curious attendees at any of the countless meetings I attend–few folks are above just coming right out and asking, “…Winfrey? Any relation to Oprah?” I actually don’t mind it because the answer is easy enough–“Yes–” but the details of how that works for me isn’t simple at all.
Having Oprah Winfrey, the richest woman in entertainment, the most powerful woman in media, the world’s first black female billionaire, and the woman who can turn an entire industry on a dime with a few words, for a cousin is quite an experience.
Besides the obvious questions about whether or not we are related, there are a few other questions that I am often asked. I’d like to share those questions and my answers to them with you today.
Please understand that I’m not here to defend Oprah, as I have had my disagreements with her on certain topics (J. L. King and the DL for one example). She has a legal team and PR people for that. This is simply about my relationship with her and my opinions about some of the things she’s done. I don’t have higher expectations of her simply because she has more money than I do. After all, in all her glory, she is still “just” another human being with her own gifts, and challenges, and my cousin.
The Frequently Asked Questions (FAQs)
FAQ #1: “Will Oprah make a donation to (or make appearances for) [this or that cause] if you send her our way?”
Answer: Probably not. She has her Angel Network and she gives to causes outside the network when she chooses. However, considering her prominence, wealth, and the level of giving at which she operates, those decisions aren’t simple for her. Where and what she gives comes with so many implications and, as has been proven time and time again, her support makes waves. She has to be thoughtful about where she puts her money becuase if one of the organizations she supports takes a bad turn, it could be a nightmare for her.
I’m sure there are more orgnizations out there she could be helping out with money, but I really feel that what she has to teach is more important than her money. She often tells people that if you have a cause and you are committed to it, then you must have faith that it will inevitably evolve into what it must become in order to fulfill its destiny.
She really wants more people to realize that money alone isn’t the solution to every problem. Commitment, hard work and giving selflessly of your spiritual gifts are priceless endowments that we can all give to the cause closest to our hearts. Oprah will also tell you that charity also begins at home (i.e., in your own heart by investing in yourself). It’s her money, and I’m not about to even try to tell her what to do with it.
FAQ #2: “Being Oprah’s relative must be helpful to get you places.”
Answer: Sure, it does. Clearly, there is some residual benefit to being a “Mr. Winfrey,” but it doesn’t work like magic because not everyone is an Oprah fan. In fact, here in New Mexico where she once owned a home, there are those who felt that she was impatient, and well, downright mean.
On this issue I will say something in her defense. When you’re used to having the world around you move as quickly as it does in a place like Chicago (or as it was for me in Philly), New Mexico can be terribly frustrating. Those that understand know that high expectations and the refusal to settle for less are important if you want to become the best at what you do, and sometimes people will resent you for it.
I don’t think that she’s being “mean” as much as I think that she’s just raising the bar. Upon the rejection of mediocrity, I’ve been called a few choice names myself. I moved here to enjoy the slower pace. So, I don’t have any complaints, but I can see how many people, especially someone like her, would.
I wouldn’t call it “clout,” but just saying the name obviously provokes a reaction. It is undeniably fodder for conversation and I have to admit, I’ve gotten more than a few clients for it who then later brag to their friends, “We have Oprah’s cousin working for us!”
Just having the last name gives people a tremendous sense of confidence in my work, and I try hard not to let anybody down. Having the expectations associated with someone like her can actually be overwhelming sometimes. However, being a “Mr. Winfrey” only goes so far because after the initial meeting, and the expected conversation about how we are related, I have to carry my own weight and earn my right to stay in the room just like everyone else.
FAQ #3: “Is Oprah your personal mentor?”
Answer: Yes, for some areas of my work, but I don’t get (or necessarily want) regular mentoring sessions with her to get advice. Whatever advice she gives can be found on her show every day anyway.
For example, one of her key messages is that we each have our own destiny and that you are the only real “mentor” you can have. At the end of the day, you have to live with the decisions you’ve made, and you cannot expect someone else to serve as guru, sage, or advisor every time you need to make a decision.
Getting advice and then putting it into practice won’t always produce predictable results anyway. Every professional must own his or her own work. Furthermore, every human being has a gift that can make them prosperous in their own right. We just have to find it. Having Oprah for a relative, or a friend, won’t really make that any bit easier. Actually, having another individual, regardless of who they are, too involved in such a process of self-discovery would not only take some of the fun out of it, it would also make it much less valuable in many other ways.
Don’t get me wrong. Mentors can be important. I can follow her in some of the things that she does because we do have a few things in common. Like her, I am talkative, a writer, have endured sexual abuse as a child, am very generous, and love Alice Walker’s “The Color Purple,” and I strongly agree with her overall message of self-responsibility and empowerment. But we don’t really do the same kind of work.
The most solid common element is that she, like I, sees herself ultimately as a teacher. Her show and her career, on the other hand, have become nothing short of American history in the making, and there are definitely elements of her work that simply cannot be replicated. There will never be another Oprah, that’s for sure.
FAQ #4: “Does she give you money?”
Answer: No, and I won’t ask for it either. Working hard for your own way is something that I would say is part of the Winfrey family ethic, if there is one. My grandparents worked hard.
My great-grand parents worked even harder. My great-great grandparents–which she and I share–worked harder still. We were all encouraged to do the same and to go to school and to find our way, like people are in many families. We were encouraged to learn to fish for ourselves. We were not taught to wait for a savior–for neither peace nor prosperity. I was taught that I’d have to find these things for myself.
How would I ever reach my potential if I picked up the phone and called her every time I had a problem? Worse yet, what if she lost all of her money and ended up broke–then what? It could happen… I believe that it is not only a sin to count other people’s money, but it is even worse to fantasize about how I would spend it.
The fantasy I shall have is in obtaining my own place in this world because that’s the only fantasy that I can actually make come true. It’s better for her to say that she has a cousin who is a graphics designer and an aspiring writer than it is for her to say that she has a cousin who is a mooch.
Yet, during times when I faced the challenges that my life has had to offer, more than a few people didn’t hesitate to quip, “Why don’t you just ask your rich cousin Oprah for some help?” It is often a total distraction and sometimes. People have also taken out their problems with her on me on more than one occasion. I guess I didn’t really get it at first.
I’ve gotten strange looks doing what many other Americans do everyday, like taking out a loan. After hearing remark after remark at a bank about how I should ask Oprah for money, I thought, “Exactly where does ‘I am Oprah’s [distant] cousin.’ go on this loan application?”
I know that I will have as much money as I have the capacity to earn and manage effectively for me.
More importantly, I don’t feel entitled to her wealth. I don’t like it when people behave as if they are entitled to me or my money either. We should be able to celebrate the success of those we love without coveting their accomplishments.
It may seem crazy that I don’t ask her for money or help, but part of what it means to be a Winfrey (or an adult regardless of your last name) means that you understand what you can do for yourself and be able to count your own blessings. This is what I believe the 10th Commandment is all about.
One blessing that we often overlook is the unique privilege it is to have been born an American. You don’t have to be a flag totin’ fool and ignore what it sometimes means to be black in America)…but it doesn’t take much to realize that those she helps outside of America need her help WAY more than most of us do.
We know that in America the possible “worst case” scenario is often better than the highest hopes for a “best case” scenario in many other places in the world, like Africa. In America we have free schools and a plethora of ways to finance further education so that everyone can get an education, and perhaps even one day become greater than Oprah. In America we also have laws that dictate what kind of treatment we should expect from each other.
They aren’t always followed, but at least America has a moral conscience or compass under the law. America is certainly not perfect, but I’m not as worried about gross human rights atrocities, a caste system or an impoverished government holding me back. If a poor little black girl from Mississippi born in 1954 can become a billionaire, then what of a middle-class black gay boy from St. Louis born in 1972–relative of Oprah or not?
The Value of My Greatest Inheritance
Obviously, education, entrepreneurship, determination–and communication–are among our most treasured family values, and they are priceless. That’s why I really don’t really need her money.
Sure, who doesn’t want a few extra million bucks to throw around?
I could definitely put it to good use, but when I see her opening schools in Africa, building homes for Katrina victims, or see the look on the faces of people who love her and are inspired by her and have had their lives changed by her show, I don’t feel that I’m the one in need of her wealth in that way. The value system that got her where she is the same one I was raised and live by anyway.
If you saw the PBS special about my family, you’ll know that our great-great grandfather Constantine Winfrey was a slave. When he became free he was listed as illiterate in the census that followed. Seven years later when the census was taken he became literate and acquired acres of land in the state of Mississippi.
It would be amazing if he did all this on his own in just 7 years, but I am actually inclined to think that his owners also helped him learn to read and write but couldn’t permit him to claim his literacy right out of slavery. If they had been found having helped him become literate, they would have been found breaking the law.
What is amazing to me, as the PBS special also mentions is that he, like Oprah, also eventually built a school on the land he owned. He built it because black children were kept from attending schools elsewhere by the Klu Klux Klan.
Having said all that, the common heritage that we share has provided me with the sense of pride and identity to create my own career and to begin building my own reputation, and Oprah can’t do my work for me. I have to get up everyday and let my light shine just like everyone else in this world. In fact, I’ll earn the right to be a guest on the Oprah Winfrey Show one day just like everyone else who gets there–for being who I am and doing what I do well.
A Family Like Any Other
While we are generally hard-working people, we also have our fair share of problems just like any other family. Both Oprah and I experienced sexual abuse at the hands of people who were not a part of our paternal family.
However, my dad, James Winfrey, Jr. died of alcoholism at 55 years of age. I was barely 16. He drove trans-continental bus lines like Greyhound for a living. After a trip out here to the Rocky Moutains when I was around 10, he predicted that I would on day find peace here and make it my home. He later was a driver for Bi-State, the local mass transit corporation in St. Louis.
My mother is still alive and she is a recovering alcoholic. She had the hardest time with my sexuality, but my father was generally a tolerant man. In fact, the Winfreys were the ones who accepted my being gay. The Winfreys are not judgmental people at all. My mother and I also have a wonderful relationship today, by the way.
As you might imagine, there are also members of the family who feel that Oprah should be more generous with them. I think that’s wrong. I think it is the most horrific violation of the 10th Commandment when covetousness exists within a family. It is nothing more than jealousy, and in my opinion–even if Oprah wanted to–I don’t think that it would be wise to put every member of your family up anyway. It’s not healthy to live off other’s people’s wealth and, as I mentioned before, it would be stifling.
Ultimately, what makes my relationship with her valuable to me is not blood, money, power or respect; it is what she has shown me, like so many other people: what is possible with intention. Even though the expectations are high, the inspiration is far more pervasive. After all, we are all standing on the backs of ancestors that brought her into this world just like every other black person in America.
Every black person in America today is great because we are the descendants of arguably the most tenacious and enduring people of our time. Being Oprah’s relative doesn’t mean that I get to cash-in on her, it just means that none of us really have excuses for why we can’t go just as far.
With thanks to Keith Boykin.
Kenneth Winfrey is a graphics and web designer, as well as a writer (and a lifetime student of religion), living in Albuquerque, NM, USA.
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