Putin Caught in an Expanding Spiderweb

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Russian transport plane destroyed as part of phase one of Ukraine’s Operation Spiderweb on June 1, 2025 (Kanal13/YouTube)

Ukraine’s Operation Spiderweb, which destroyed at least 10 percent of Russia’s strategic bombers with AI-programmed FPV drones that were smuggled and activated inside Russia, may not reverse mounting defeats suffered by its undermanned army in the ground war. But the highly developed covert warfare capabilities demonstrated by the Ukrainian intelligence service (SBU) may prove a wild card in negotiations with Putin, who faces setbacks in the Middle East and on other fronts.

“Ukraine is hitting and will hit Russia where it considers itself unreachable,” said SBU chief Vasyl Malyuk, stressing that its targets are military installations from which Russia attacks “peaceful Ukrainian cities.” Judging from Russia’s retaliatory onslaught in which about 500 Shahed drones, ballistic and cruise missiles pounded Ukraine every night over several days, the destruction of some of its Soviet-era Bear bombers doesn’t seem to have amounted to much. (RELATED: Russia’s Aerial Assault on Ukraine)

But hitting strategic bases thousands of kilometers inside Russia, some located in Siberia and the Arctic region “will force Russia to redeploy air defenses to protect strategic assets in rear areas and deep in Russia at the expense of front-line forces that may be left exposed,” according to Blackwater CEO and ex-Navy SEAL Eric Prince.

The immaculately planned and coordinated Spiderweb strikes are the latest demonstration of the SBU’s technical and engineering proficiency. Its Magura maritime drones have already made military history by neutralizing Russia’s Black Sea Fleet and securing Ukraine’s vital commercial sea lanes. Newly developed submarine drones hit the Kerch bridge connecting Russia with Crimea on June 2.

Ukrainian Espionage

Operation Spiderweb also indicates that Ukraine has a significant agent network in Russia and its Eurasian surroundings. Intelligence analysts believe that the mobile wood cabins with fake solar panel roofs into which the strike drones were loaded and transported by tractor trailers to their targets may have entered Russia from bordering central Asian states with ethnic Muslim populations historically hostile to Moscow.

False flag operations could have been used to recruit agents and contract services from local criminal organizations engaged in extensive smuggling and human trafficking. A year ago, an ISIS cell based in Dagestan staged a terrorist attack on a music festival on the outskirts of Moscow, and the group tried escaping to Ukraine.

While the June 1 drone assault was controlled from Ukraine according to SBU sources, safe locations in Russia were used for storage and maintenance of the 117 FPVs launched in the attacks. According to analysts, their batteries needed to be kept charged during the long trek to their targets and would have required locally minted Russian SIM cards. The final preparations were carried out in the western Siberian city of Chelyabinsk, right under the noses of Russia’s security service (FSB), which has offices nearby.

“Covert special operations units are managing Russian cells acting against a variety of targets inside Russia,” an SBU source told The American Spectator in Ukraine, a year ago. They routinely conduct surveillance and provide intelligence on munitions, drones, and aerospace plants, which have been sabotaged and struck by drones with growing frequency. A drone strike against the Kremlin in 2023 could only have been launched within the vicinity of Moscow, according to experts.

Assassinations have also targeted Russian officers accused of war crimes, including a high-ranking general in charge of biological and chemical warfare programs who was blown up by a car bomb in the center of Moscow last month. Locally staged sabotage bombings of railway lines transporting troops and supplies to Ukraine were coordinated with the drone assault on air bases.

According to the Ukrainian intelligence source, guerrilla cells are activated and given instructions by phone calls from SBU handlers in Ukraine. Funds are transferred using PayPal or other internet services. While members of the underground opposition to Putin may be too exposed and subject to Russian police surveillance to use in sensitive armed operations, SBU often recruits hit teams and support personnel for its covert warfare from among marginalized social groups such as migrant workers, criminal street gangs, and drug addicts.

The Russian FSB

Russia’s secret services have been similarly recruiting alienated youngsters or even old people to conduct arson and sabotage attacks in Europe, often through the use of online methods. An anarchist group that recently blacked out parts of southern France and is threatening to attack the defense industry is believed to be a creation of Russia’s military intelligence service, GRU.

It’s difficult to see how Ukraine’s secret service can operate to the extent that it does inside Russia without having penetrated the FSB, whose relations with Putin have been problematic throughout the war. Putin purged the FSB following his disastrous attempt to take Kyiv at the start of his Ukraine invasion in 2022. The rout of Russian tank columns outside Kyiv and the elimination of commando teams sent to assassinate President Zelenskyy have been blamed on double agents who fed deceptive intelligence to Moscow.

Some 200 FSB officers were arrested and sent to the notorious Lefortovo prison, including the head of the 5th directorate, Sergey Beseda, responsible for operations in Ukraine and Eastern Europe. It appears that FSB agents were feeding false information to Moscow about local support for a Russian invasion, and that covert funds to finance an uprising in support of Putin largely disappeared.

The FSB failed Putin again during the 2023 Wagner Group mutiny when it neglected to provide adequate warning about Wagner chief Prigozhin’s coup plans. FSB officials used the crisis to regain leverage on Putin, who relied on the spy service to round up Prigozhin’s suspected sympathizers in the army and arrange for his elimination.

Purged FSB officers have been brought back into service, including Beseda, who recently turned up with Russia’s negotiating team sent to Istanbul for peace talks with Ukraine. But discrepancies between Putin and his intelligence services are ongoing. Last week, the New York Times revealed an FSB report, whose veracity was checked through U.S. intelligence analysts, referring to China as an “enemy” using its growing business presence in Russia for “espionage.” It was leaked just as Putin hosted CCP leader Xi Jinping at Moscow’s annual Victory Day celebrations. China has been a vital source for electronic components needed for Russia’s war production, particularly in the manufacture of missiles and sophisticated strike drones. (RELATED: Splitting Xi From Putin: A Comfortable Delusion)

It may be years before we know if SBU moles have been lurking inside the FSB. But an internal atmosphere rife with corruption, power struggles, and mutual distrust that appears to plague Putin’s underperforming intelligence agency seems ripe for exploitation by hostile secret services.

Russia and the Middle East

Putin’s setbacks in other areas are also playing to Ukraine’s advantage. His loss of military bases in Syria, where Russian naval and air facilities are being shut down by the new Islamic government headed by insurgents who toppled his ally, Bashar al-Assad, and have established relations with the U.S., diminishes his leverage on Israel, which no longer fears Russian retaliation for challenging Putin.

Operatives of Ukraine’s military intelligence unit HUR reportedly assisted the insurgent push against Assad last year. HUR is engaged in paramilitary activities against Russia throughout Africa and other parts of the world.

Israel’s ambassador to Ukraine, Michael Brodsky, said in an interview last Sunday on Ukraine’s Pravda state television, that Israel has sent “several” MIM-104 Patriot batteries to Ukraine in what is a clear change of policy by Tel Aviv, which had remained largely on the sidelines of the Ukraine conflict until now.

Israel’s transfer of American air defense systems, along with continued U.S. deliveries of interceptor missiles, allowed Ukraine to withstand Russia’s massive missile bombardment in response to Spiderweb.

Ukraine intercepted Russian Shaheds, Iskander ballistic missiles, Kh-101s, and other cruise missiles at a rate of 80 percent during the first few nights of bombardment, reaching 100 percent by June 9, according to Ukrainian defense spokesmen.

Without its position in Syria, there is also little Russia can do to protect Iran from Israeli air strikes aimed at destroying its nuclear facilities that began this week. Russia has transferred some of its Su-35 fighter jets to Iran over recent months, but Putin is being forced to play the peace card, having offered to store Iranian enriched uranium, which Israel and the U.S. want moved out of Iran as part of any deal with the Ayatollahs.

With a weakened geo-strategic position while President Trump threatens sanctions to cripple his oil industry and the SBU points a dagger to his throat, Putin could decide it’s best to settle for a peace deal while he still wields the upper hand on the battlefield — even if a future Check Point Charlie between a free western Ukraine and his reconstituted Russian empire has to be further east from where he envisioned.

READ MORE from Martin Arostegui:

Russia’s Aerial Assault on Ukraine

US Intelligence Downplays Maduro Partnership With Tren De Aragua

The Future Is Dim for US–Canada Relations

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