LEMON DROP | Making Medicare Simple with Chapter CEO Cobi Blumenfeld-Gantz

In today’s Oval Office meeting with Canadian Prime Minister Carney, Trump once again leaned into his favorite fantasy: annexing Canada. After Carney firmly asserted that Canada is not for sale, Trump smirked and replied, “Never say never.” Yes, this is real life. As America spirals through economic instability and global backlash, Trump is out here cosplaying land baron like it’s 1867. This kind of strongman land-grab nonsense isn’t just embarrassing, it’s isolating the U.S. further on the world stage. Let's break down the latest diplomatic facepalm and what it says about Trump’s obsession with power, borders, and ignoring reality. This episode is sponsored by Shopify. Sign up for your one-dollar-per-month trial and start selling today at SHOPIFY. COM/lemon This episode is sponsored by BetterHelp. Give online therapy a try at betterhelp.com/donlemon and get on your way to being your best self. This episode is brought to you by the Freedom From Religion Foundation. Whether you’ve always been secular or left religion behind, if you don’t want someone else dictating the trip for you, F-F-R-F has your back. Join us. Go to FFRF.US/Freedom or text the word, “DON” to five eleven five eleven and become a member today. Text fees may apply. Learn more about your ad choices. Visit megaphone.fm/adchoices

6 Touko 20251h 12min

Today we are joined by Samantha Barry, Editor-in-Chief of Glamour magazine, to unpack everything we saw at last night’s Met Gala. From bold looks to unexpected guests to the theme hits (and misses), we’re diving into the red carpet chaos and cultural conversation behind fashion’s biggest night. Who nailed it? And what does it all say about where fashion and celebrity is headed next? Learn more about your ad choices. Visit megaphone.fm/adchoices

6 Touko 202526min

Because nothing says “freedom” like bringing back Alcatraz, Trump has now floated the idea of reopening the infamous prison island. Yes, that Alcatraz, the one we turned into a museum because we thought we were done with locking people away on remote rocks. So… why now? And who does he plan to put there? (Spoiler: it’s probably not white-collar criminals or corrupt politicians.) Is this just another MAGA stunt? Or are we watching the early stages of state-sponsored prison camps take shape right before our eyes? Let's break down the absurdity, the authoritarian undertones, and the truly dystopian vibes coming from the Trump administration’s latest "idea." Because apparently the 2025 policy agenda is now just one bad Netflix thriller at a time. This episode is sponsored by Shopify. Sign up for your one-dollar-per-month trial and start selling today at SHOPIFY. COM/lemon This episode is sponsored by BetterHelp. Give online therapy a try at betterhelp.com/donlemon and get on your way to being your best self. This episode is brought to you by the Freedom From Religion Foundation. Whether you’ve always been secular or left religion behind, if you don’t want someone else dictating the trip for you, F-F-R-F has your back. Join us. Go to FFRF.US/Freedom or text the word, “DON” to five eleven five eleven and become a member today. Text fees may apply. Learn more about your ad choices. Visit megaphone.fm/adchoices

6 Touko 202548min

It’s another chaotic day in the news cycle, and we’re breaking it all down. First up: Trump’s interview with Kristen Welker, where he served up a fresh batch of lies, deflections, and victimhood, and then cried “unfair” the moment she pushed back with facts. (We’ve seen this movie before. It never gets better.) Then we head to Georgia, where Governor Brian Kemp just announced he’s not running for Senate, potentially clearing the way for a possible run by none other than Marjorie Taylor Greene. Because apparently we’re trying to hit that “worst-case scenario.” And finally, we’ll cover the latest in the Diddy case, where jury selection has officially begun in what’s shaping up to be one of the most high-profile and controversial trials of the year. Politics, ego, and celebrity scandal...welcome to a typical Monday in America. 🍋 This episode is sponsored by Shopify. Sign up for your one-dollar-per-month trial and start selling today at SHOPIFY. COM/lemon This episode is sponsored by BetterHelp. Give online therapy a try at betterhelp.com/donlemon and get on your way to being your best self. This episode is brought to you by the Freedom From Religion Foundation. Whether you’ve always been secular or left religion behind, if you don’t want someone else dictating the trip for you, F-F-R-F has your back. Join us. Go to FFRF.US/Freedom or text the word, “DON” to five eleven five eleven and become a member today. Text fees may apply. Learn more about your ad choices. Visit megaphone.fm/adchoices

5 Touko 20251h 3min

This weekend, Trump sat down with Kristen Welker, and—shocker—it went exactly how you'd expect. He made a parade of false and misleading claims, dodged every substantive question, and the moment he was actually pressed on facts? He whined that the interview was unfair. Because in Trump World, being held accountable = media bias. Same script, different day. Let’s get into it. This episode is sponsored by Shopify. Sign up for your one-dollar-per-month trial and start selling today at SHOPIFY. COM/lemon This episode is sponsored by BetterHelp. Give online therapy a try at betterhelp.com/donlemon and get on your way to being your best self. This episode is brought to you by the Freedom From Religion Foundation. Whether you’ve always been secular or left religion behind, if you don’t want someone else dictating the trip for you, F-F-R-F has your back. Join us. Go to FFRF.US/Freedom or text the word, “DON” to five eleven five eleven and become a member today. Text fees may apply. Learn more about your ad choices. Visit megaphone.fm/adchoices

5 Touko 202558min

Welcome to The Sour Lemon Special! Every week, we break down the most outrageous, corrupt, and downright awful behavior from the people in power—and this time, we’ve got a stacked lineup of contestants. Who will take home the title of this week’s Sour Lemon? You decide! Join Don and comedian Jay Jurden to break it all down! This episode is sponsored by Shopify. Sign up for your one-dollar-per-month trial and start selling today at SHOPIFY. COM/lemon Learn more about your ad choices. Visit megaphone.fm/adchoices

2 Touko 20251h 3min

This morning, we’re diving into Trump’s increasingly authoritarian agenda because the vibes aren’t just bad, they’re fascist-adjacent. First up: Harvard. Trump’s declared war on the Ivy League, now threatening to revoke the university’s tax-exempt status because they didn’t align with his political narrative. Free speech? Academic freedom? Apparently not when it makes Dear Leader uncomfortable. Then there’s the Alien Enemies Act, a centuries-old law Trump is now using to deport people en masse. A federal judge just ruled that his use of the law exceeds its legal scope. So the question is: Will they listen to the courts? Or are we just tossing the Constitution out the window for good? Don breaks down the legal overreach, the political revenge, and how much longer this democracy can function with this level of power abuse. Spoiler: It’s not looking great. This episode is sponsored by Shopify. Sign up for your one-dollar-per-month trial and start selling today at SHOPIFY. COM/lemon Learn more about your ad choices. Visit megaphone.fm/adchoices

2 Touko 202557min

Tonight on The Don Lemon Show, we’re breaking down the utter madness that is today’s news cycle because the Trump administration just pulled another political stunt straight out of the chaos playbook. First, Mike Waltz is out as National Security Advisor. Then, plot twist! He’s suddenly named U.N. Ambassador just hours later. And who’s filling in as National Security Advisor? None other than Marco Rubio, because apparently being Secretary of State just isn’t keeping him busy enough. Joining Don to make sense of the nonsense is Congressman Suhas Subramanyam, who’s been on the front lines pushing back against Trump’s policies and power grabs. It’s reshuffling, it’s reckless, and it’s all happening in real time. Buckle up, Lemon Nation. This episode is sponsored by Shopify. Sign up for your one-dollar-per-month trial and start selling today at SHOPIFY. COM/lemon Learn more about your ad choices. Visit megaphone.fm/adchoices

2 Touko 202544min