Jen Psaki Has Doozy of a Trump Question for Dem Who Flipped Mar-a-lago District

MS NOW host and former Biden White House press secretary Jen Psaki asked Florida state Rep.-elect  Emily Gregory (D) a doozy of a question about President Donald Trump amid her victory in the district that houses Trump’s Mar-a-Lago resort.

Gregory emerged victorious on Tuesday in a Florida House of Representatives special election against Trump-endorsed Republican Jon Maples in a district Trump won by 11 points in 2024. The 87th district is also home to Mar-a-Lago.

On Wednesday’s edition of MS NOW’s The Briefing with Jen Psaki, Psaki cut right to the chase in her interview with Gregory, asking herm “What do you think about the fact that Donald Trump is now one of your constituents?”:

JEN PSAKI: Well, first of all, congratulations. I mean, I can’t — I don’t think I can repeat for viewers who are tuning into this enough. I mean, Trump won this district by 11 points in the last election. The Republican who formerly held the seat before he resigned, Mike Caruso, previously won it by 19 points. You’ve just flipped the seat tonight. How are you feeling?

STATE REP-ELECT EMILY GREGORY (D-FL): Jen, it’s a pretty wild night. I — right when I started this nine months ago, I obviously thought it was possible. I think most people thought I was insane looking at the numbers. But, I mean, I still — I’m still like pretty shocked. We did it. We just did it.

PSAKI: What do you think about — there’s so much to ask you about, but what do you think about the fact that Donald Trump is now one of your constituents?

GREGORY: I mean, I don’t think all of that much about it, right? He’s one of 115,000 registered voters in District 87. My opponent made, you know, him forefront in his campaign. And I focused more on the voters in District 87. You know, what everybody needs, what all of us will do better with, with lower property insurance, with expanded health care, and with strong public schools.

PSAKI: So you answered part of my next question. But let me ask you, I mean, you said when you started, when you told friends, when you announced you were running, people thought you were insane. I’m sure a lot of your friends and family said, why are you doing this? How are you going to win in this district? Have you seen how Republican this district is? But for people out there who are thinking about it or who are doubting it, what — how did you win? What would you tell them is your advice about how to kind of flip a district like this?

GREGORY: Jen, I love that question. And I say, go for it. I say, back yourself, you know? It only takes you getting off the sidelines to make a difference. And if you want the world to look different, then you have to go out and make it different. I think we’ve learned over the last several years that no one is coming to save us, we have to save ourselves. So I might have done some crazy calculus to decide that this was a flip opportunity, but it was. And we did it. So my math worked.

Watch above via MS NOW’s The Briefing with Jen Psaki.

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