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Oprah Winfrey reflects on brother's 'extremely cruel' death at 29 in impassioned message — the heartbreaking story

The legendary media mogul honored her late brother Jeffrey Lee in honor of Pride Month

Beatriz Colon
Beatriz Colon - New York
New York WriterNew York
June 5, 2024
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Oprah Winfrey is reflecting on her late younger brother Jeffrey Lee's untimely — and unjust — death when he was 29, 35 years ago, in honor of Pride Month.

The billionaire media mogul, 70, had a famously difficult upbringing; she was born into poverty in rural Mississippi in 1954 to a teenage single mother, Vernita Lee, and father Vernon Winfrey, who never married Vernita, a coal miner and later barber and city councilman.

Jeffrey, born in 1960, was her half-brother by way of their mother, and in honor of Pride Month, the former talk show host opened up about his death in 1989 from AIDS-related causes.

In a clip shared on the Oprah Daily Instagram, Oprah first said: "It was 35 years ago that my younger brother Jeffrey Lee died from AIDS. He was 29 years old."

She continued: "The year was 1989, and the world was an extremely cruel place," noting: "Not just for people suffering from AIDS, but also for LGBTQ people in general."

The AIDS epidemic – which in the U.S. was infamously mishandled by former President Ronald Reagan – is considered to have begun in June of 1981. The World Health Organization reports that to this year, it has claimed the lives of approximately 40.4 million people across the world since then.

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Oprah further reflected: "I often think if he'd lived, he'd be so amazed at how much the world has changed. That there actually is gay marriage and a Pride Month."

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The concept of Pride Month began with the Stonewall riots in New York City's Christopher Street, specifically at the still-existing gay bar the Stonewall Inn, in June of 1969; activist Marsha P. Johnson has been largely credited as being one of the first to incite the movement. 

Oprah Winfrey speaks onstage at the 35th Annual GLAAD Media Awards held at the Beverly Hilton Hotel on March 14, 2024 in Beverly Hills, California© Getty
Oprah at the recent GLAAD Media Awards in Los Angeles

Former President Bill Clinton formally recognized it as Pride Month in 1999, ironically, three years after he signed the Defense of Marriage Act into law, which declared that no state could be required to recognize a same-sex marriage performed in another state. Same-sex marriage was legalized nationwide in June of 2015, with the landmark Supreme Court decision Obergefell v. Hodges.

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A sign at 'The Stonewall Inn', a Gay bar, National Historic Landmark and site of the 1969 riots that launched the gay rights movement is seen on June 4, 2019 in New York City© Getty
A plaque outside the historic Stonewall Inn

Oprah continued her Pride Month message by wondering "how different" her brother's life "might have been, had he lived in these times, in a world that saw and appreciated him for who he was, rather than attempting to shame him for his sexuality."

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Stedman Graham and Oprah Winfrey attend an event at the White House in Washington, D.C., on June 27, 1989© Getty
Oprah with her partner Stedman Graham in June of 1989, months before her brother's passing in December

She maintained: "I believe that every single person has a right to love who they want to love, and be the person who they most want to be, and my hope for you is that you are living a life that feels authentic to you, and that you have the support around you to do so, no matter your sexuality."

"And whether or not you are celebrating Pride this month, or always, I wish for you the continued freedom to rise to your truest, highest expression of yourself as a human being."

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