Countdown to Midterms: 3 Weeks to Go
Anderson Cooper 360
October 14, 2026
With just three weeks left in the campaign, President Trump spent nearly 8 hours on a plane to a state that should have been safely red in the first place, while his handpicked new press secretary is being panned for her debut performance.
Speakers John Berman, Katie Zachariah, Donald Trump, Kristen Holmes, David Axelrod, Karine Jean-Pierre, Peter Meijer, SE Cupp, Ari Shapiro, Sanjay Gupta, Kaitlan Collins, Armando Raju, Roger Marshall, Adam Hamilton, John King, Abby Norton
TopicsNews
John Berman (0:04)
With just three weeks left in the campaign, every day counts. And for the president, this one might count as a doozy. Nearly eight hours on a plane to a state that should be safely read in the first place with a handpicked new press secretary who's being panned for her debut performance, a performance that included the political whacking of his former future daughter-in-law for asking a donor to foot her $100,000 AMEX bill.
John Berman here in Fort Anderson, and this is midterms 2026 countdown to election night. The president is in Alaska where you might be able to see Russia from your house, but it is telling that he's spending one of his remaining 21 days there at all. No other voters in bordering states to hear his message, unless Eastern Russia counts. Then again, it's not like the president had the best of all days to have his message heard. It began, as we said, with his new press secretary breaking the awkward news that Kimberly Guilfoyle, his scandal-prone Greek ambassador, was through.
SPEAKER_2 (1:05)
The president said yesterday to reporters that he is considering firing her. Do you know a timeline for that? And also potentially who could be on the short list to replace her if he does?
Katie Zachariah (1:16)
We have asked Ambassador Guilfoyle to resign. She has been a wonderful asset to the team and we wish her well.
Okay.
John Berman (1:26)
Okay.
So there was that. And not long after that, the press secretary herself became the story. Reviews of her performance started coming in and not just from critics and pundits, but more to the point, from inside the White House, one official called her debut, quote, brutal. Others described it as unusual, awkward, stilted, and at times uncomfortable. Some other comments, why did they put her out there so quickly? And quote, literally zero reason to put her out on her second day unprepared. Again, that's from inside the White House. She spoke for 14 minutes and called on just three reporters, so there was that, too.
The president, on the other hand, said he thought that she was, in his words, very good. He also acknowledged that Alaska was a long way to travel, but said it was worth it to help incumbent Senator Dan Sullivan. He is stumping for a candidate who won re-election in 2020 by nearly 13 points, and it has been this way throughout the race so far, stop after stop, in one red state after another, trying to boost candidates who once might have been shrewins. And as we reported last night, even some Republicans wish he would just stay away instead of insisting as he does at most stops, that voters pretend that he is on the ballot, 33, 34 percent job approval, four plus dollar a gallon gas and all. And the perception among voters, fair or not and true or not, is that he is less focused on that and more on other things.
Donald Trump (2:49)
Does anybody want to see a great work of art, a great thing of beauty? Absolutely. The helipad, right? The helipad has got unbelievable architecture reviews, but that's nothing compared to what's being built right there. You see those cranes? They're the most powerful cranes in the world. They're lifting up massive steel beams.
There's one on each side.
John Berman (3:16)
Seen as Kristen Holmes is traveling with the president, she joins us from Wasilla, Alaska. Kristen, what message does the president have for voters in Alaska tonight?
Kristen Holmes (3:27)
Well, President Trump is going to double down on the message you just laid out, which is pretend I am on the ballot. And it is stunning, Don, that he is here three weeks before this election. This is a state that hasn't backed a Democrat for Senate in nearly 20 years, yet he is spending all of this time on a plane just for what? Two hours to support the incumbent senator, Dan Sullivan, in this race. Now, we've seen a lot of Republican candidates kind of shy away from Donald Trump. That is not what we have seen from Senator Sullivan. He was up here moments ago talking about how great Donald Trump was. We know that he supported the war in Iran, saying that it's something that had to be done. He's voted against the War Powers Act. And he even at times has said the economy will bounce back after this war in Iran is over. He was standing next to President Trump in the Oval Office a few weeks ago when they announced that deal with South Korea, talking about the natural gas pipeline, which of course has had some dispute around it. But it just goes to show you that they really believe that President Trump is popular here, that he has that enthusiasm level. And if they can drive out the voters by bringing him here, then they can actually get some of those Republicans who might have sat on the couch instead out to the ballot box in November. One thing, John, that we cannot let lie is the fact that this time around, because of Alaska's unique voting structure, there are two Dan Sullivans on the ballot. One is the incumbent, the other is a retired school teacher. We talked to a lot of voters here who are worried about that confusion as well.
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