SKIP BAYLESS WAS RAISED in Oklahoma City, primarily by Katie Bell Henderson, an African-American woman employed by his grandmother. “My parents were both pretty much disasters—alcoholics both,” he said. Although Oklahoma City was still segregated, he spent summers with Ms. Henderson’s granddaughter Audrey, who would periodically visit from Chicago. Mr. Bayless, whose brother is celebrity chef Rick Bayless, said that growing up around African-Americans was crucial in shaping him. “Everything I learned about life, I learned from Katie Bell—rights and wrongs, principles,” he said, adding, “I had a great connection [with African-Americans]. When we played the black teams, they always liked me. They called me Skippy. They would kid with me after the games.” Nonetheless, he hastens to add, “I don’t try to be black. I don’t want to be the white black guy. I don’t do that.”
Mr. Bayless has told his First Take debate partners—the majority of whom are African-American—about Katie Bell and her influence on him, though he admitted, “I don’t know if this offends them or if they take it the wrong way.”
Mr. Bayless was a talented athlete growing up. He played basketball and baseball and was a rival of a future World Series MVP, the late Darrell Porter. A high school English teacher pushed him into journalism, and Mr. Bayless took to it, casting himself as a provocateur from the outset. In one of his first columns for the school paper, he trashed the baseball team’s manager (never mind the fact that Mr. Bayless was the team’s starting catcher).
After graduating from Vanderbilt University, Mr. Bayless worked for the Miami Herald and then the Los Angeles Times, where he broke the news of Joe Namath’s retirement. A committed teetotaler—“I got fed hard liquor when I was 3, 4, 5 at some of my parents’ parties, which they thought was funny”—Mr. Bayless made an exception after the flamboyant quarterback invited him to a bar in Long Beach to get the scoop of a lifetime. Two glasses of red wine later, Mr. Bayless wound up flat on his back, and the story had to wait a day. (These days, he said, Diet Mountain Dew is his only vice.)
He became the star columnist for the Dallas Morning News at 25, and was quickly poached by Dallas Times Herald. Mr. Bayless made his name covering the Cowboys. He was tough on legendary coach Tom Landry, and was early to report the dysfunctional relationship between Mr. Landry’s replacement, Jimmy Johnson, and team owner Jerry Jones. Eventually, he wrote three books on the franchise, the last of which, Hell-Bent: The Crazy Truth About the ‘Win or Else’ Dallas Cowboys, touched on the feud between Mr. Johnson’s successor, Barry Switzer, and star quarterback Troy Aikman. The book is somewhat notorious for Mr. Bayless’s investigation into Mr. Aikman’s sexuality.
“Switzer began to hear that Troy was bisexual—it was everywhere in Dallas,” he told The Observer. “Barry started asking media people if we were aware of this. He challenged me and others, ‘Why don’t you tell the truth about Troy?’” Mr. Bayless was accused of trying to out Mr. Aikman (who denied the rumors) and slammed by his peers. “His gay take on Aikman was the most unfair thing in my 45 years in journalism,” former Morning News sports editor Dave Smith told author Jeff Pearlman.
“He said that because he didn’t get the story,” Mr. Bayless said. “I obliterated the Dallas Morning News reporters from start to finish on that story. If you read the book, you will conclude that Switzer is a maniac and Troy is the hero. I’m very proud of that book.” Nobody who actually read it, he insisted, “would conclude Troy was bisexual or gay.”
Some of the details were pretty sleazy—especially an anecdote about Mr. Aikman turning down “one potential Miss Texas after another” at a country and western bar. Then again, a head coach and his supporters trying to smear their quarterback is a legitimate story, however tawdry it might be to report.