That wasn’t all. He did late-night radio work on WFAN and the early-morning sports gig on Channel 2. He wrote a series of children’s books with Ronde, a defensive back with the Tampa Bay Buccaneers. He helped launch the Yes! Network’s football programming and guested on everything from Cash Cab, Celebrity Family Feud and Wait, Wait, Don’t Tell Me to Iron Chef America.
The breakthrough came in 2005, when he signed on as a guest host on Fox & Friends. It was no coincidence that Mr. Barber’s football career had also resumed in earnest. After the knee injury healed, he’d developed into one of the top offensive players in the game. When he hung up his spikes at the end of 2006, he had an array of high-profile offers, ultimately spurning big money from Fox to jump to NBC.
“If we had to do it over again, Tiki probably should have stayed at Fox,” Mark Lepselter, Mr. Barber’s manager, told The Observer. “They knew him, and they knew his work ethic there. He had some goodwill vested.” At NBC, not so much. It probably didn’t help that Mr. Barber had conducted his job search in the most high-profile way possible, punctuating his transition from All-Pro running back to network correspondent with a New Yorker profile proclaiming the rise of “Tiki, Inc.” and accompanied by a topless portrait.
By 2007, Mr. Barber’s marriage to his college sweetheart Ginny was already on the rocks. They separated once, then reconciled, and were in the process of splitting up for good when The New York Post dropped a bombshell. Mr. Barber, who was 34 at the time, was leaving his pregnant wife for a 23-year-old NBC intern named Traci Lynn Johnson. Two months later, NBC canceled Mr. Barber’s contract. Tiki says that his relationship with the network wasn’t working anyway, and that he was ready to move on. The tabloids reported that NBC invoked its morality clause.
Whatever the cause, Mr. Barber was out—hanging out at home with Ms. Johnson, whom he would later marry, watching television for hours on end. “I literally was waking up, having breakfast, finding an old show on Netflix, Cheers or Roseanne or Dr. Quinn, Medicine Woman,” he told us. “And I was getting bored; I felt myself mentally losing it.”
It was an odd repose for a figure who’d spent the better part of his 20s courting the public eye. Early in his career, Mr. Barber came under the wing of Giants co-owner Bob Tisch, and when Mr. Tisch passed away, Tiki was asked to speak at the funeral. “I said, ‘Bob had a lot of great accomplishments, but I think his greatest accomplishment might be that he made a young black kid from the South feel like he was Jewish’”—an anecdote The Observer took to mean that Mr. Barber felt connected to Manhattan society.
He sent his kids to school at the 92nd Street Y, and peppers his conversation with casual references to various hedge funds.
“Back in the day, I used to say we had the keys to the city,” Tiki’s manager Mr. Lepselter told us. “There was virtually nobody who was more than two phone calls away.”
In the aftermath of his dismissal, old friends pulled away. It didn’t help that he’d taken a public shot at Giants quarterback Eli Manning in an early TV appearance, or that Mr. Manning had gone on to lead the Giants to the Super Bowl that year.
Perhaps it also hurt that Mr. Barber had thrown away a sports career for what he deemed a higher calling—not just yukking it up on the pregame show, but doing real journalism. He has hardly done an interview about his media career that doesn’t include references to his meetings with Condoleezza Rice and Shimon Peres.
“I’m complex, and that turns people off sometimes,” he told us over omelets later in the day at the Trump SoHo. “I’m not simple—I’m not in a box. I’m not just an athlete or football player or journalist.”
At the suggestion of a college friend, he went to meet Mark Gerson, co-founder and chairman of the expert network company Gerson Lehrman Group. The two men soon became a striking pair—a muscle-bound athlete and a reed-thin businessman, united perhaps by their hyperproductive natures (in addition to his entrepreneurial work, Mr. Gerson is the author of two books and the chairman of an emergency ambulance service in Israel).
Together, they quickly identified a problem: athletes often retire with valuable brands but have no way to cash in.