For any spiritually minded, up-wardly mobile African-American living in Chicago in the mid-1980s, the Trinity United Church of Christ was—and still is—the place to be. That's what drew Oprah Winfrey, a recent Chicago transplant, to the church in 1984. She was eager to bond with the movers and shakers in her new hometown's black community. But she also admired Trinity United's ambitious outreach work with the poor, and she took pride in upholding her Southern grandmother's legacy of involvement with traditional African-American houses of worship. Winfrey was a member of Trinity United from 1984 to 1986, and she continued to attend off and on into the early to the mid-1990s. But then she stopped. A major reason—but by no means the only reason—was the Rev. Jeremiah Wright.

According to two sources, Winfrey was never comfortable with the tone of Wright's more incendiary sermons, which she knew had the power to damage her standing as America's favorite daytime talk-show host. "Oprah is a businesswoman, first and foremost," said one longtime friend, who requested anonymity when discussing Winfrey's personal sentiments. "She's always been aware that her audience is very mainstream, and doing anything to offend them just wouldn't be smart. She's been around black churches all her life, so Reverend Wright's anger-filled message didn't surprise her. But it just wasn't what she was looking for in a church." Oprah's decision to distance herself came as a surprise to Wright, who told Christianity Today in 2002 that when he would "run into her socially … she would say, 'Here's my pastor!' " (Winfrey declined to comment. A Harpo Productions spokesperson would not confirm her reasons for leaving the church.)