He's expected to counter the U.S. Anti-Doping Agency's portrayal of him as the mastermind of what it called the most sophisticated, professional doping program in the history of sports by saying that doping was endemic to cycling during the era in which he won his record seven Tour de France titles.
He also is expected to deny that he forced his teammates to dope along with him, pointing out that some U.S. Postal Service riders used performance-enhancing drugs before they joined the team.
And according to a personal familiar with the conversation, he'll confront USADA's portrayal of him as a vindictive thug, a characterization underscored by video clips Winfrey shows him of hostile statements he made about those who questioned his claim of competing clean.
It's unclear how the two-and-a-half hour conversation, which was taped in an Austin, Texas hotel Monday, will be broken into two segments. It's also unclear what will compel viewers to return for Friday's installment (9 p.m. ET) after they've had a chance to judge for themselves Armstrong 's level of sincerity and contrition Thursday night.
Armstrong started the process of atonement last weekend, calling former teammates and key figures in cycling to apologize. Before Monday's taping, he visited the headquarters of Livestrong to address roughly 100 there.
Meantime, his lawyers continue working behind the scenes to mitigate Armstrong's legal exposure and chart a path for a possible return to competition, which would require the World Anti-Doping Agency to lift its lifetime ban.
To succeed in either endeavor will require Armstrong to do far more than confess his doping and express regret on television. He'll have to repay a portion of the roughly $35 million in federal funds that bankrolled the U.S. Postal Service Cycling team, for starters, and provide both federal and anti-doping officials with detailed information about how he and his peers got their performance-enhancing drugs and skirted detection for years.
Depending how he comes across on television, Armstrong may find a measure of forgiveness among the American public. But according to sports-marketing experts, he'll find it virtually impossible to reclaim any role as a corporate pitchman for years to come — if ever.
"The marketplace is inundated with marketable athletes," says David Schwab, managing director of Octagon First Call, which helps corporations, agencies and non-profits assess the value of celebrities in marketing campaigns. "Presently it would be reckless to recommend him to a brand, with all the other possible options and the inherent risk and possible backlash of working with him,"
Armstrong is hardly the first sporting superstar to suffer a cataclysmic fall from grace.
But there is a vast difference between his transgressions and those of Tiger Woods, for example, whose serial philandering cost him lucrative sponsorships and resulted in a self-imposed exile from golf, during which he underwent therapy. But Woods has since returned to competition, the cheers of the gallery and a new Nike ad in which he's paired with Rory McIlroy.
"We've seen athletes who area seeking marketing deals after indiscretions rebound," Schwab noted, "but they seem to rebound if they have cheated on their spouses more so than cheated on the game."
Chicago-based sports marketing consultant Marc Ganis said Armstrong's first goal on what will be a long road to redemption should be to simply not be viewed as a pariah.
"There's an old saying, 'The cover-up is worse than the crime,' and that's where his problem comes in," Ganis said. "Cheating in cycling was rampant. Anybody who has followed that sports understands that now. If he was simply one of those cheaters, it would be like anyone who gets stopped by a cop for speeding saying, 'Officer, I was just going the speed of traffic!' The impact would have been far, far less.
"Instead, he held himself out to be the one honest man in a sea of dishonesty. He held himself out to be this bastion of doing things right. And anybody who fared challenge him was trashed. He lied under oath. He lied to the media. He hurt quite a few people who dared challenge the mythology of Lance Armstrong. He built himself a perch so high, that when he came down, there was no safety net."
Jim Andrews, senior vice president of IEG, a sponsorship consultant firm, sees no future for Armstrong in the marketing arena.
"Even if he comes off as very contrite and apologetic, if Oprah gets him to break down in tears and say, 'I'm sorry, this was a huge mistake,' it doesn't wipe away the fact there is a years-long record of cheating," Andrews said. "If I'm controlling the marketing dollars for a corporation or a brand, there is no positive message I can attach myself to by a partnership with Lance."
Among those who'll be watching is Daniel Coyne, author of "Lance Armstrong's War" (2005) and co-author of Tyler Hamilton's 2012 confessional, "The Secret Race."
Coyne expects Armstrong will be straightforward but steer away from contrition and discussions of right-and-wrong.
"The way he approaches the world is highly strategic," Coyne says. "He sees a goal and figures out exactly what he has to do to reach the goal, no matter what it is. That ruthlessness and clear-headedness helped him on the bike. But in this situation, it ended up being his trap.
"When you say the word 'confession,' it's an act of communication and emotion. It's not something you can win. And Lance is about winning. His lack of an ability to connect with people is what helped him to succeed. Now, he needs that. And whether or not he has that ability to connect — that is a Greek story."
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