Jason Calacanis Was Warning Trump About the Midterms: The Signs Were There January 2025, post-Inauguration “I was a ‘Never Trumper,’ and now I am rooting for him wholeheartedly to do great work.” “He has to stay with the 2.0 agenda, as hard as it is, and stay away from the Steve Bannon agenda and the grifting. Those are the things that will take this all apart. So that's my appeal to them.” March 2025, after Kristi Noem’s visit to a prison in El Salvador “I believe that there is a sadistic nature to this administration. It is an Achilles' heel for them. And when you see them doing videos from these prisons and saying, ‘This is going to happen to you,’ this is why they will lose the midterms if they continue to do this type of stuff.” October 2025, after Trump’s net approval hit a new low “It's not pretty for Trump right now. Liberation Day when he did the tariffs, then the LA protests, remember the violent protests, and the ICE agents chasing people down in fields, not releasing the Epstein files in July. They don't like the chaos. The Democrats are going to shellack the Republicans in the midterms if this continues.” November 2025, after inflation hit 3% in the September ‘25 print “Trump sold people that prices would go down. We're back up to 3% inflation, folks. Not only is it not going down, it's going up. Trump has failed the middle class. That's the bottom line here.” March 2026, after the US and Israel strike Iran, kicking off the war “This is kind of the end of Trump's second term, and if you were to put together the series of mistakes that he's made, they're really at the heart of why people voted for him. You take starting a war like this, specifically with Iran, that's what we were told was the reason to vote for President Trump. He was not going to take us down this path. If this continues for another six months, it's basically going to result in the Democrats doing a clean sweep in the midterms.” June 2026, after the Iran War exceeded initial timelines “It’s just a huge, colossal error starting this Iran War, and hopefully we can get out of it. We can't be in a forever war, obviously.” October 2026, on Midterm predictions “All I have to say is, Trump promised not to start a war, he did. He promised to solve inflation, he didn't. The end. And I think the Democrats sweep.”