Oprah Winfrey
Kevin Winter/Getty Images for NAACP Image Awards

If I were a betting man, I’d wager that Oprah Winfrey will run for political office at some point. And if I lost that bet, I’d mos def put a dollar straight on the possibility that she is—at the very least—figuring out how to be the progressive black female version of the Koch Brothers.

Recent movements suggest it’s not a matter of if but when.   

A bored, bigoted rich white guy with a bad comb-over and a leaned-in eBay CEO shouldn’t be the only nontraditional politicos who can catch that fire in the belly. Why not a sister with more than enough millions to dump into a race and the global brand recognition to capture the imaginations of eager voters?

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We can rightly assume that Winfrey’s latest media-empire transitions are simply part of her continuing evolution as a successful businesswoman who is keeping her brand alive. With her having gone from syndicated talk show host to cable network owner, there’s not much doubt that she’s looking to carve out a permanent branding space. Every opportunity leads back to Oprah-centric success and feeds into her estimated $3 billion-plus value.

And even though her brand has taken enormous hits since the 2011 cancellation of her trend-setting eponymous show (such as the steep 22 percent drop in O, The Oprah Magazine readership), it’s not as if they were fatal blows. She’s still sticking around. We’d be surprised to wake up tomorrow and read a headline that Oprah had gone belly-up.

But what’s intriguing about Winfrey’s trajectory is her shrewd entry into the political marketplace, even if it risks taking bites out of her business model. She could easily have played it safe in 2008 and not endorsed then-candidate Barack Obama in the Democratic presidential primary, avoiding the permanent ire of her loyal white female fan base who either backed Hillary Clinton or skewed right in favor of McCain-Palin in the general election. Instead, she unapologetically put all her chips on the table and has found herself in recovery mode ever since. 

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Still, Northwestern University’s Craig Garthwaite and the University of Maryland’s Timothy Moore concluded that in doing so, Winfrey delivered more than a million votes for Obama—which was crucial, considering that he beat Clinton by only 280,000. Those numbers suggest that Winfrey commands the kind of political draw that could prove useful in, say, a statewide U.S. Senate bid (Illinois, where she originally blew up, being a good place to start). A million votes averages out to about 20,000 voters in every state—or translates into even more votes in a state that’s friendly to the whole notion of a Sen. Winfrey. 

Her latest moves are by no measure reckless. They are calculated maneuvers that push the boundaries of her brand and experiment with embedded public-policy platforms: Profits from her Teavana-Starbucks partnership will support youth education; she’s also endorsed controversial charter school initiatives, dipping into fairly choppy and controversial waters; and she’s kept the South African girls’ leadership academy alive, despite road bumps and criticism. Notwithstanding that themes in personal enrichment and women’s empowerment frequently populate OWN narratives, Oprah is eager to make targeted policy points.

The question is whether she wants to make those points as a political candidate or as an influential partisan rainmaker. She didn’t stop with Obama, regularly cutting checks to state Democratic committees and the Democratic National Committee. She made a statement with a $10,000 check in 2012 to 21-year-old Stockton, Calif., City Council candidate and now Councilman Michael Tubbs, who is one of the nation’s youngest in that position. 

Last year’s special-election cycle found her putting money and fundraising time into then-Newark, N.J., Mayor Cory Booker’s U.S. Senate bid. Nearly $30,000 dropped into the coffers of Booker and the New Jersey Democratic State Committee. Oprah had found herself another winner. In 2014 she has injected herself into yet another campaign, this time on the House level for nonprofit exec Laverne Chatman, Virginia’s 8th Congressional District candidate. That may have locked up a win for Chatman in the crowded Democratic primary to replace retiring Rep. Jim Moran. It’s a particularly significant development in a northern-Virginia district that’s 17 percent black and represents the wave of demographic change in a former Confederate capital and battleground state, once reliably red but now electing Democrats statewide. 

Obviously Winfrey is no different from any other billionaire seeking clout through carefully plotted campaign contributions. And she’s clearly building a network of highly polished African-American elected officials who represent the new age of black politics. 

But there is a certain political flash and openness about her moves that pique interest from both admirers and detractors watching her consistently place winning campaign bets. Oprah looks good, and she’s still got many years ahead of her. Why waste them on talk shows in perpetuity? That she’s not quiet about her politics triggers suspicion that she’d be open to launching her own campaign rather than sit back quietly and move chess pieces. 

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No one has yet asked about her political aspirations, thus feeding the impression that she’s merely content with history seeing her as a pop-culture icon who puts selfies on her magazine’s cover. It depends on whether she chooses to jump in after so many years of doing the same damn thing. If you had that much money and that kind of background, wouldn’t you consider a future in politics?

We can be confident that she has no appetite for or interest in a presidential campaign. Besides, according to YouGov, she’s got some pretty high national negatives with those white women who won’t let her forget 2008. But Gallup still found that she was the second-most-admired woman in the world in 2013—right behind Hillary Clinton and a point ahead of Michelle Obama. She’s still ranked (pdf) with President Obama and Clinton as the top three “progressives,” thereby giving her enough pull within Democratic Party ranks to run for an open Senate seat.   

Northwestern’s Garthwaite, however, is not convinced that she’s going to run for anything. “Winfrey has certainly increased her involvement in politics since 2008,” he said in an email response to The Root. “That being said, I haven’t seen any indications that she would want to be involved in politics directly.”

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Yet one thing we know for sure is that she’s still on a quest for the next best stage to make her point—which, with each passing cycle, is looking more and more like the foundation for a campaign platform. Oprah’s incessant self-promotion and marketing machine should raise flags that she would be inclined to make some dramatic jump into the political horse race. My bet is that she does. She’s just trying to figure out the exact parameters of that play and how to go about it to ensure a win on the first try.    

Charles D. Ellison is a veteran political strategist and frequent contributor to The Root. He is also Washington correspondent for the Philadelphia Tribune and chief political correspondent for Uptown magazine. Follow him on Twitter.

Charles D. Ellison is a veteran political strategist and a contributing editor at The Root. He is also Washington correspondent for the Philadelphia Tribune, a frequent contributor to The Hill, the weekly Washington insider for WDAS-FM in Philadelphia and host of The Ellison Report, a weekly public-affairs magazine broadcast and podcast on WEAA 88.9 FM Baltimore. Follow him on Twitter.