INTREP360 INTELLIGENCE REPORT
06.23.2026: VLADIMIR PUTIN'S 'CRI-ME-A' RIVER PART II
June 23rd, 2026
Greetings!
Three years ago today, Yevgeny Prigozhin, a man we once argued was aiming to be Russian President Vladimir Putin’s king, began his Wagner Group mutiny against the Kremlin by marching northward from Belgorod to Moscow.
Prigozhin failed. Exactly two months later the private military company chief was assassinated when a private jet carrying him exploded and crashed on the outskirts of the Russian capital killing everyone on board.
Russia, in retrospect, might have been better off had Prigozhin succeeded. Certainly, he was no hero. In many ways, he was the classic definition of a psychopath and his reign of terror extended from Russia to Ukraine to the Sahel in Sub-Saharan Africa.
Early on, Prigozhin strategically understood something Putin still does not. The Russian military, on a conventional basis, is incapable of defeating Ukraine. Now, Putin is at risk of losing Crimea, the Ukrainian peninsula that he illegally seized and annexed in 2014.
The writing was on the wall that this day was coming as early as late 2022. We noted then at The Hill in Washington, D.C. that Putin’s swan song might be in Crimea.
Photo credit: Vantor. Oil tanks on fire near the Kerch Bridge in Russian-occupied Crimea on June 21st, 2026.
In doing so, we pointed out that Putin could ill afford to lose Crimea militarily or symbolically — especially since the peninsula then afforded Russia critical land-based access to its naval base at Sevastopol.
Yet now that facility is largely empty courtesy of Ukraine. It was once home to Moscow’s Black Sea Fleet and the Kremlin’s primary means of projecting power throughout the Black Sea and into the NATO-dominated Mediterranean.
Once upon a time, Crimea’s air defense assets and coast defense units located on the strategic peninsula guarded Russia’s southern flank from NATO. Fast forward to today and many of those assets are destroyed and Russian forces are struggling to defend their southern flank from Ukrainian attacks.
NATO, as a result, would have a cakewalk into Russia’s southern flank if Putin were ever foolish enough to attack the West as he did yet again today. Putin can talk the talk, but the reality is his military can no longer walk the walk.
Since Prigozhin’s mutiny, Russia’s losses have been staggering. As we noted at the time, Russia had already incurred more than 100,000 casualties, lost an estimated 50 percent of the Ukrainian territory it seized in the opening days of Putin’s ‘Special Military Operation,’ and was being forced to dig in in the Donbas and Crimea.
As of today, Russian dead and wounded in Ukraine are nearly 14 times greater. In addition to 1,394,530 casualties, Russia’s economy is imploding. Plus, its armies, despite small tactical gains in the Donbas, are effectively stalled, and the Armed Forces of Ukraine (AFU) are increasingly taking the war to Moscow and St. Petersburg.
The AFU is also getting closer and closer to turning Crimea into the decisive terrain of the war. Indeed, as Robert “Madyar” Brovdi, the Commander of the Unmanned System Forces of the AFU, said today, “Moscow will fall in Ukraine.”
Let’s get started finding out how.
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CRIMEA IS SINKING
Putin likely started this war believing that the Crimean peninsula was his strategic equivalent of British Prime Minister Winston Churchill’s Fortress Singapore during the early years of World War II.
In Churchill’s mind, Singapore Island was an unsinkable aircraft carrier. The strategic island is located at the southern end of the Malay Peninsula in Southeast Asia and Churchill believed it was impenetrable.
On February 8th, 1942, the Japanese Imperial Army proved him wrong by landing three divisions on the island. One week later, Lt. Gen. A.E. Percival, the commander of a 90,000 British Commonwealth army, was forced to surrender. It was the largest single British military loss in the United Kingdom’s history.
Putin, no doubt given his fondness of history, gets the parallel and sees — indeed, likely fears — the same thing happening to him in Crimea. Churchill was able to survive the loss of Singapore in large part because it was overshadowed by the U.S. entry into World War II.
Putin likely cannot survive the loss of Crimea. The Russian President started this war as a would-be Peter the Great. He is likely to end it as a disgraced modern-day Rasputin.
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CRIMEA IS BURNING
As we pen tonight’s edition of the INTREP360 Intelligence Report, there is breaking news that the AFU attacked “a large Russian weapons depot in Kirovske, Crimea.” Note the Russian name is Kirovskoye. The small town that houses a Russian military base is located in the southeastern part of the peninsula.
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TURNING CRIMEA INTO A SINKABLE ISLAND
Essentially, the AFU is methodically turning Crimea into an island. Getting here today began in the early days of the war when Ukraine began to systematically destroy Russia’s vaunted Black Sea Fleet.
It was a remarkable undertaking given that Ukraine effectively has no navy to speak of. The AFU’s success at sea is largely being accomplished by naval drones and unmanned aerial attacks on Moscow’s ships and submarines. Ditto the Russian navy’s air defense assets.
The Kremlin’s inability to protect its base in Sevastopol forced Russia to begin moving what was left of its Black Sea Fleet to Novorossiysk and other Russian bases. By February of this year, the fleet was all but gone from Crimea.
Simultaneous to the AFU’s pummeling of Putin’s Black Sea Fleet, Kyiv also began systematically destroying Russia’s air defense assets on the Crimean Peninsula. Now, as Ukraine’s latest deep- and medium-strike weapons are coming online en masse, Crimea is more exposed than ever to AFU aerial strikes.
Yet it is not just the growing vulnerability of Crimea itself that is endangering Putin’s hold on the peninsula. It is the AFU’s multi-layered assaults on the Kremlin’s supply lines — sea, land, and air — that are slowly setting up Crimea for the kill.
Putin’s vaunted land bridge — a bridge he once dreamed of expanding westward all the way through the Ukrainian Black Sea port of Odessa to Moldova — is under daily attack by Ukrainian drones. Traffic is now limited to military vehicles and convoys.
Slowly but surely, Ukraine is choking Moscow’s ability to sustain its military forces on Crimea. Ditto its civilians and Russian tourists who still, despite the war, continue to flock to the Black Sea’s picturesque beaches. As noted by reporting in the Washington Post today, Russians are reporting widespread fuel shortages across Crimea.
Only the $4 billion Kerch Bridge remains linking Crimea to the Russian mainland. That is, it remains for now. The AFU appears to be setting conditions to drop the Kerch Bridge in the coming weeks.
We think we know when it is likely to happen. But we are not out to help Russia figure that out at Ukraine’s expense, so for now we will keep it to ourselves. Purely as a marker, take note of ‘220.’ We will let you know if we got it right or wrong.
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TURNING THE LIGHTS OUT
The AFU is actively working to make Crimea untenable. As Fox News reported earlier today, Ukraine “hit a railway bridge, a power plant and other key sites as part of an effort to isolate the peninsula from Russian supply lines.”
Plus, the Kyiv Independent is reporting that more than half of Crimea is without electricity today due to fuel rationing and AFU strikes on critical energy infrastructure. Putin is notorious for weaponizing winter against Ukraine. Chalk one up for Zelensky by weaponizing summer against the Russians in Crimea.
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PUTIN IS IN DENIAL
Putin does not appear to get it that he is on the verge of losing. Yet again today, he acted as if there was nothing to see here, implying that victory was assured in the long run.
Denial is a thing.
However, Putin should take note of one thing. Purportedly, the talk of the G7 Summit in Geneva last week was how impressed President Donald Trump was with Ukraine’s unrelenting deep strikes in Russia.
Suddenly, although we never doubted it, Ukraine has a lot of cards to play. Expect Zelensky and his generals to play more of them in Crimea.
When they do, let Putin’s swan song finally begin: ‘Cri-me-a River.’
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ICYMI #1
Earlier today, in our regular weekday foreign affairs column at The Washington Star, we examined the White Elephant in the room when it comes to the Memorandum of Understanding between the U.S. and Iran: Hezbollah.
Either Hezbollah gets disarmed and disbanded or peace in the Mideast, including peace between the U.S. and Iran, is not likely to happen any time soon.
Photo credit: White House. JD Vance did not address the Lebanon issue in Switzerland Friday.
You can read it here. It is not paywalled at our request.
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ICYMI #2
Mark was on Alghad TV News in Cairo, Egypt earlier today. His fellow guest panelist, an Iranian regime supporter, appeared from Iran.
Predictably, he argued Iran was in the right, the U.S. in the wrong, and that Tehran essentially had all the cards. He also claimed that Iran would not allow unfettered International Atomic Energy Agency (IAEA) snap inspections.
Mark countered saying without them then the MOU would be dead on arrival on Capitol Hill and eventually at the White House.
You can watch it here. The segment is in Arabic. Mark’s half hour appearance begins after the 30-minute hash mark.
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Jon & Mark
Follow Jon on X at @JESweet2022 or on Bluesky at @JonSweet.bsky.social. Follow Mark on X at @MCTothSTL or on Bluesky at @MarkToth.bsky.social.