May 28, 2026
Thursday. The Ken Harbaugh Show. And this time he’s not in a studio — he’s at an undisclosed location in Ukraine, which tells you everything about how seriously this man takes the work.
We spent the hour on a simple question: who’s actually winning? Because if you only read the headlines, you’d think Russia is on the march, and Trump is closing peace deals. Both of those things are backwards. Russia is losing so badly it’s resorting to threats it can’t back up, and Trump’s “deals” are press releases with a countdown clock.
Let’s get into it.
🎙️ Who Is Ken Harbaugh?
Ken Harbaugh is a former U.S. Navy pilot and mission commander who flew combat reconnaissance missions off North Korea. Yale Law School grad. Producer of the documentary Against All Enemies. His bylines run through the New York Times, The Atlantic, The Bulwark, and NPR. He hosts The Ken Harbaugh Show, and when he says something about military reality, it’s because he’s lived it — not because a think tank emailed him talking points.
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Subscribe to him. Seriously. I’ll say it again at the bottom.
💣 BOMBSHELL #1: Lavrov Called Rubio to Threaten Kyiv — And Showed Russia’s Hand
Here’s what happened, confirmed by Russia’s own Foreign Ministry readout and tracked across Western and Ukrainian outlets.
On May 25, Sergey Lavrov phoned Marco Rubio to “officially inform” Washington that Russia is beginning “systematic, continuous strikes” on Kyiv — including what Moscow calls the “decision-making centers” of the Ukrainian government. Then he told Rubio the United States should evacuate its diplomats and citizens from the capital before it happens.
Read that again: the Russian Foreign Minister called the U.S. Secretary of State to say we’re about to bomb the seat of a sovereign government, you might want to get your people out.
Ukraine’s Foreign Ministry called it exactly what it is — blackmail. Foreign Minister Andrii Sybiha said Ukraine won’t succumb to it and pointed the obvious question back at the Kremlin: Putin “needs to save his country, if he still can.”
And here’s the tell. The head of the EU mission in Kyiv, Katarina Mathernova, refused to budge — “We are not going anywhere!” — and called the warning a masterpiece of hypocrisy. Her key line, the one Ken kept coming back to:
Such threats are not a sign of strength. They are a sign of desperation.
That’s the whole episode in one sentence. France and Poland rejected it too. Nobody fled. The threat landed with a wet thud.
Ken’s read, and he’s earned this read: you don’t announce strikes on a capital’s government buildings through a leaked phone call if you’re winning. You do it when your battlefield options are shrinking, and you need the psychological win because the military win isn’t coming. Putin signed legislation the same day, authorizing military deployments abroad to “protect Russian citizens” — paperwork, not progress. Russia has had the capability to hit central Kyiv for years, and historically hasn’t. The announcement is theatre. Desperate theatre.
⚔️ The Part the Doomscrollers Miss: Ukraine Has Russia on the Brink
This is where Ken — live from Ukraine — flipped the entire narrative.
The story you’re being sold is “Russia escalating, Ukraine struggling.” The story on the ground is the opposite. Ukraine’s long-range strikes have been chewing into the Russian economy and Russian infrastructure to the point where the Kremlin is rattled. When the side with the bigger army starts threatening to bomb city halls and begging foreigners to leave, that’s not the behavior of a confident power. That’s a cornered one.
Ken’s framing: the Ukrainian people aren’t just holding the line. They’ve put Russia in a position where its own war supporters are asking the most dangerous question an autocrat can face — for what? Same trap we talked about before with the Z-bloggers turning on the Kremlin. When the people who built the war start losing faith, you’re in the endgame.
The Ukrainians aren’t winning despite the noise. The noise is the evidence they’re winning.
🤡 BOMBSHELL #2: Trump Tried to Truth-Social His Way to a Peace Deal
Pivot to Iran, because it’s the same disease in a different theater.
I wrote a whole piece this week on Trump’s “deal” with Iran, so here’s the short version for the LIVE crowd: it’s not a peace deal. It’s a 60-day memorandum of understanding — an agreement to schedule talks — and as of this recording, Trump hadn’t even signed it. He asked for “a couple of days to think about it.” Iran is disputing portions of what U.S. officials claim was agreed to. And there were two skirmishes in the Strait of Hormuz within 48 hours, while everyone called it a breakthrough.
Ken’s point cuts deeper than mine: this is the Truth Social theory of diplomacy. You post that a deal is “largely negotiated,” you let the headlines write themselves, and you hope the announcement creates the reality. It’s governance by press release. The actual terms? Iran reopens the strait it closed, sells its oil, gets the blockade lifted, and keeps the right to enrich — and the hard nuclear questions get punted into a 60-day window that can be extended forever.
The guy who tore up the JCPOA, calling it the worst deal in history, just signed up for something with no enrichment cap, no stockpile number, and no inspections in the document. He’s surrendering and calling it a win — because on Truth Social, declaring victory and achieving it are the same thing.
Ken’s military read on why: when your Gulf allies have stopped returning your calls, and your leverage is evaporating, you take the meeting, and you spin it. A weak hand played loud is still a weak hand.
🎸 BOMBSHELL #3: The Freedom 250 Concert Lineup Imploded in Real Time
And now the part that made me genuinely laugh on camera.
The Trump-backed Freedom 250 celebration — the official-ish machinery for America’s 250th birthday, born out of a White House task force — rolled out the lineup for its “Great American State Fair” on the National Mall. And friends, the lineup is a time capsule nobody asked to open: Vanilla Ice, Milli Vanilli, Flo Rida, Bret Michaels, C+C Music Factory, The Commodores, Martina McBride, Young MC, and Morris Day & The Time.
It’s the soundtrack to a 1991 roller rink that’s being foreclosed on.
But here’s the actual story. Within hours of the announcement, the acts started bailing:
Morris Day & The Time posted that, “contrary to rumor,” they will not be performing — adding the all-time kiss-off, “It’s a no for me.” And note that word: rumor. It’s not even clear he was ever booked. The organizers may have just slapped his name on a poster.
Young MC — yes, “Bust a Move” — pulled out the same day, saying flatly: “The artists were never told about any political involvement with the event.” He noted the organizers call it nonpartisan while Spin calls it Trump-backed, and said he’d love to play D.C. at something “not so politically charged.”
C+C Music Factory’s frontman first signalled he’d quit, too, then reversed in an eight-minute, expletive-filled Instagram video, mostly to prove commenters couldn’t tell him what to do.
Read that again: performers found out they were booked at a Trump event by reading the announcement that booked them. That’s not a concert lineup. That’s a hostage list. The organizers were so desperate for marquee names they apparently advertised acts who hadn’t agreed to show up.
Ken’s macro point, and it’s the through-line of the whole hour: this is what a dying brand looks like. When you can’t get C-list nostalgia acts to play your country’s 250th birthday without them sprinting for the exits, the problem isn’t the talent budget. It’s the brand. Trump’s name has become so radioactive that Milli Vanilli is a reputational risk calculation.
Trump’s SIM card isn’t working anymore. People aren’t picking up. Not the Gulf states, not the Ukrainians, not Sergey Lavrov’s threats landing on anybody, and — apparently — not the guy who sang “Wild Thing.”
🎯 The Through-Line
Ken and I closed where we always do: document the collapse in real time.
Look at the three stories. Russia is so far from winning that it’s reduced to threatening a capital it can’t take and asking diplomats to please leave first. Trump is so far from dealmaking that he’s surrendering to Iran and posting victory. And the regime is so radioactive that washed-up 90s acts won’t share a stage with its birthday party.
These aren’t three stories. They’re the same story. Power that has to announce itself this loudly is power that’s already gone. Desperation doesn’t whisper — it calls Rubio, it posts on Truth Social, it books Morris Day without asking.
The Ukrainians know it. The Gulf states know it. Morris Day knows it.
Our job is to make sure you know it too.
These LIVES go twice a week. Show up. Bring your Republican uncle.
— Dean
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📰 Sources: Russian Foreign Ministry readout, Kyiv Independent, NBC News, Ukrainska Pravda, Japan Times, CNBC, Axios, Variety, The Hollywood Reporter, Billboard, Washington Times, WUSA9, WJLA
Thank you Lev Parnas, PJ Schuster, 🇨🇦 Natalie Woodn’t 🇨🇦, Pamela, Sheryl, and many others for tuning into my live video with The Ken Harbaugh Show! Join me for my next live video in the app.
