As of September 3, 2026, Polymarket prices “Will Anna Kelly be the next White House Press Secretary?” at 28% YES with $51K traded. No tracked smart-money wallet holds a position on this market yet.
Prediction markets put the probability at 28%: Will Anna Kelly be the next White House Press Secretary. Currently, markets see this as unlikely (28% YES). Two-thirds of users believe Scott Jennings will ultimately get the nod.
Speculation over the successor to White House Press Secretary Karoline Leavitt, who is departing the role at the end of August 2026, has centered on a short list of Trump loyalists, with the question of who will be the anna kelly next white house press secretary pick drawing steady attention. Anna Kelly, the principal deputy press secretary, has handled media appearances for the White House while Leavitt was on maternity leave, though she has never led a formal briefing. Conservative commentator Scott Jennings, who appears on CNN, emerged as the betting favorite in mid-August after attorney Alina Habba publicly removed herself from contention. [WWMT, Aug 13]
The field remains crowded. As of Aug 25, roughly two-thirds of Kalshi users favored Scott Jennings, while about 23% backed Anna Kelly. RNC national spokesperson Elizabeth Pipko and Communications Adviser Margo Martin each sat near 7%, with Natalie Harp at 5%, Communications Director Steven Cheung around 4%, and Alina Habba at 2.5%. By Aug 31, Kalshi bettors had moved Kelly to the top of the list at 27%, reflecting how quickly sentiment around the anna kelly next white house press secretary question has shifted as other candidates faded. [Federal News Network, Aug 25]
The outcome matters because the press secretary is among the most visible administration roles, shaping daily messaging from the briefing room. Observers expect President Trump to favor a loyalist willing to "hit back hard," a profile that fits several contenders. Habba, now a senior adviser to the attorney general, said on Aug 31 she would accept the job if offered despite earlier ruling it out, adding late uncertainty. Political adviser Katie Miller has also been floated. With Leavitt's exit imminent, a formal announcement of the anna kelly next white house press secretary decision—or another name—is anticipated in the days ahead, and Kelly's lack of prior briefing experience remains a noted variable. [Washington Times, Aug 31]
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