Oprah at a crossroads

Talkshow host mulls next steps for lucrative brand

Over the past 25 years, no one has been more adept at discerning what women want than Oprah Winfrey. Yet as the host faces her latest “what next?” career decision, the multimillion-dollar question is, “What does Oprah want?”

Put simply, Oprah’s choice is whether to continue her syndicated TV show or migrate to cable when her current contract expires in August 2011. Moving would be a major boon to her latest venture — a partnership with Discovery to launch something modestly known as the Oprah Winfrey Network — which already has undergone management changes and generally un-Oprah-like pre-launch tumult.

Inasmuch as Winfrey has nothing left to prove, no mountains left to climb in daytime TV, she could view OWN as her next major challenge. In the past, however, the host has always realized that everything ultimately flows out of the daytime series — the TV testing ground, by the way, for many of the “experts” she plans to feature in OWN shows, along with those dashing doctors of daytime, Phil and Oz.

Winfrey’s Harpo Prods. isn’t saying what she’ll do, having promised an announcement before the end of the year. But to understand how the host might envision her future requires some familiarity with the spirits of “Oprah” past and present.

The young Winfrey began as a local talkshow host in Chicago, then successfully expanded onto a national stage in 1986. After a time, she deviated from the tawdry topics that originally characterized her program (and most of the genre) and emerged as more than just a TV personality — adding a magazine, promoting books, producing movies and TV, and in the process becoming a billionaire.

Somewhere along the way, Winfrey forged a bond with her audience that went well beyond the customary “You watch me, I entertain you” relationship. Instead, she transformed herself into a kind of latter-day guru — counseling people to “live your best life,” while offering hints and tools regarding how to do so.

Winfrey has also aligned with some shady characters as part of that effort — occasionally endorsing a bogus memoir or sounding as if she were helping peddle self-help snake oil. Such miscues generally haven’t diminished her connection with viewers, though she did exhaust some capital among conservatives by endorsing then-candidate Barack Obama — the ultimate “my favorite things” seal of approval.

The “Oprah” evolution has assumed a missionary quality — as the host tries to lead her people (that is, the millions of women, mostly, who tune in daily) to their particular promised lands.

The issue Winfrey must grapple with now is how best to achieve that. A TV host can always retire, or migrate from one national platform to

another; by contrast, a movement leader needs to weigh options differently — wondering not what will earn her the most money (she’ll make out fine either way), but rather what will most effectively advance the larger “best life” agenda.

Can she do more good by giving up syndication to help put OWN on the map? Or is she better off keeping the mother ship in orbit, casting a warming light on her other endeavors?

For CBS, which inherited “The Oprah Winfrey Show” in absorbing King World, there’s nothing to do but sit back and let Winfrey sort this all out for herself — recognizing that while the void she leaves would be formidable, the blow wouldn’t smart quite as much as if she’d hung up the gloves several years ago.

Meanwhile, Winfrey will be back in the spotlight next week when she hosts Sarah Palin, marking the first stop on the former Alaska governor’s book tour. It’s a savvy maneuver on both fronts — offering Winfrey an opportunity to demonstrate how evenhanded and gracious she can be despite having campaigned for Obama, while allowing the once and possibly future politician to humanize herself in what should be a relatively softball interview.

Both Winfrey and Palin, in fact, are at something of a crossroads in terms of the path that lies ahead. And while it’s not clear that Palin can elevate her game to play at the next level, experienced Winfrey-watchers would almost surely caution those inclined about betting against the host.

Because, usually, whatever Oprah wants, Oprah gets.

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