June 19, 2026
I went LIVE today with former Danish Defence Intelligence officer and ex-UN Security Council member Jacob Kaarsbo, because when the news cycle is moving this fast and this stupid, you don’t want a pundit — you want a guy who spent 15 years writing classified threat assessments for a NATO service. We hit three stories on three different fronts, and Jacob’s read on all of them was the same one I keep landing on: the strongman model is cracking in real time, and the people selling you “America’s winning” are ahead of the facts.
Story One: The $300 Billion “Surrender” That Died Before Breakfast
I asked Jacob to put his intel hat on and tell me whether I was being hyperbolic calling Trump’s Iran deal a surrender bribe with a pinky-swear attached. He was not kind about it.
Here’s the through-line we walked through: Trump signs a 14-point MOU with Iran on Wednesday, struts around calling it “unconditional surrender,” and the thing is room temperature by Friday. Point one of his own document — the immediate, permanent ceasefire on all fronts, with Lebanon and Hezbollah and Israel named explicitly — gets blown to pieces when Israel bombs southern Lebanon overnight, killing at least 18 people across eleven towns. Iran looks at the smoke, points at clause one, and says: void. Delegation’s not getting on the plane to Switzerland. Deal’s off.
Jacob’s framing from the intelligence side was sharp: you don’t need to prove Bibi intended to torpedo the deal. The behavior speaks for itself — Israel kept bombing the exact country the agreement told it to stop bombing, less than 24 hours after signatures dried, while Netanyahu’s cabinet trashed the deal in the press. Sabotage or just Bibi being Bibi, the result’s identical. Dead on arrival.
And then JD Vance went on a podcast and said the quiet part into a live mic — calling Israel’s reaction a “freakout,” scolding the Smotrich/Ben-Gvir wing, and dropping “you can’t just kill your way out of solving every problem.” When a Republican VP is airing the alliance’s dirty laundry on the New York Times feed instead of in a back room, that’s not a disagreement. That’s a divorce conversation in front of the kids.
Jacob’s bottom line: Iran signed, walked, gave up nothing, and got to look like the reasonable party citing the deal’s own text. The art of the deal was always the announcement.
Story Two: Ukraine Made It Rain Black Oil on Moscow
Then we got to the part that actually has Jacob’s old service paying attention — Ukraine’s biggest strike on Moscow since the full-scale invasion began. Hundreds of drones across more than a dozen Russian regions. The Moscow Oil Refinery in Kapotnya — ten miles from the Kremlin, run by a Gazprom subsidiary — on fire for the second time in a week. Commuters filming smoke they’re legally not allowed to film, asking each other “what is going on?”
I wanted Jacob to keep me honest here, because the online takes have the causation backwards. This is revenge. Russia torched the 975-year-old Kyiv-Pechersk Lavra — a UNESCO site, the most sacred Orthodox landmark in Ukraine — on June 14-15. Ukraine answered by lighting up the refinery that fuels the war machine. Ukraine didn’t bomb a cathedral. Russia did.
But the part Jacob lit up about wasn’t the fireballs — it was the supply-chain war underneath them. The “logistical lockdown.” Fuel depots, ammo dumps, rail bridges in occupied Crimea. Refinery strikes have doubled since the start of 2026, and the independent monitor DeepState clocked May as the first monthly net decline in Russian advances since 2023. You can’t run an army on a gas tank that’s on fire. From a guy who spent his career reading these patterns: the momentum flipped. For the first time in two years, the arrow isn’t pointing Moscow’s way.
We kept it honest on the rest, too — Ukraine has not swept Russia out of the east, Zelensky did not walk out of the G7 with a signed Patriot deal (he asked for a production license; Trump was “very positive,” nothing’s inked). And Carney’s line from Evian is the one worth sitting with: “Russia is not winning, and we have to push Putin to end this war.” Jacob’s read — when the powerful people funding a war stop asking “can Ukraine survive” and start asking “how fast can we make Russia stop,” that belief becomes its own weapon.
Story Three: Greenland Laughed Uncle Sam Out of the Room
And then the one that made both of us laugh, because Jacob’s Danish and this is personal for him: the continued, deeply embarrassing US effort to annex Greenland — this time dressed up as “oil exploration deals” pitched to locals.
The pitch, as I understand it: roll into Greenland, wave around American oil money, and buy your way to influence with people who supposedly can’t say no to a payday. There’s just one problem with that plan. Greenlanders have no need for US oil money. They’ve got their own resources, their own self-determination, a Denmark that has their back, and exactly zero interest in becoming a 51st-star fantasy in Trump’s Arctic cosplay. The delegations got laughed out of the room.
Jacob’s intel-side point cut deeper than the comedy, though: this is the same strongman playbook failing on a third continent. The assumption that everyone has a price, that pressure plus money equals compliance — it keeps running into people who simply aren’t for sale. Iran cited the text and walked. Russia’s losing the supply war it started. Greenland told a superpower to pound sand. Three stories, one through-line.
About Jacob — and Where to Subscribe
If you don’t know him yet: Jacob Kaarsbo spent 15 years inside the Danish Defence Intelligence Service (FE) — Denmark’s equivalent of the CIA’s analytic branch — with deep specialties in Russia, the Middle East, and Euro-Atlantic security. He’s a former UN Security Council delegation member and the author of Subverted (Danish: Undergravet), a working intelligence assessment of the threat Trump’s America poses to its own allies. When a man who wrote classified threat assessments for a NATO service tells you the strongman model is cracking, you put the phone down and listen.
Do yourself a favor and subscribe to his work — intelligence and international security, straight from someone who did it for real:
Huge thanks to Jacob for the time. Share this with someone who still thinks the bluster equals the result.
Thank you Cat: Poli-Psych, Cash Flow Collective, Caro Henry, Grace Lovelace, Noble Blend, and many others for tuning into my live video with Jacob Kaarsbo! Join me for my next live video in the app.
