Gilbert Doctorow: Is Ukraine’s Military Nearing Collapse?

TL;DR

Ukraine’s military is nearing a politically dangerous breaking point but has not completely collapsed, according to Professor Gilbert Doctorow. He describes disastrous losses and withdrawals across Donetsk, Zaporizhzhia, and Kherson, while arguing that Russia advances slowly to draw Ukrainian forces into destructive counterattacks. The discussion also covers the Doha attack and the June bombing of Iran. Read on for Doctorow’s wider interpretation of these events.

Transcript

Hi everyone, Judge Andrew Npalitano here for Judging Freedom. Today is Tuesday, September 9th, 2025. Professor Gilbert Doctoro joins us now. Professor Doctor, I know you're uh traveling figuratively and literally, and I appreciate very much the time you've given us and what you've gone through to make this connection so we can chat. I do want to sp... Read More

Key Insights

• The Ukrainian military is suffering disastrous losses across the Donbas, particularly in Donetsk, and in neighboring oblasts including Zaporizhzhia and Kherson on the right bank of the Dnieper, withdrawing under Russian pressure while still retaining an army.
• Russia has no plans to advance beyond the Dnieper River, but may seize Odessa and large parts of other oblasts, which is not the same as wiping out the Ukrainian army entirely.
• Russia's slow, methodical approach is interpreted as deliberately baiting Ukrainian counterattacks then slaughtering them, choosing to destroy manpower rather than pursue fleeing enemies as pure military doctrine would dictate.
• The Israeli Defense Forces attacked Hamas negotiators approaching a session in Doha, Qatar, killing 37 who were about to address Trump's proposals for a cessation of military activity in Gaza.
• The United States is complicit in the Doha attack because it controls Qatari airspace, meaning Israel would need US permission to enter with jets or missiles, permission that was obviously given.
• According to Doctorow's European parliamentary source, the US June bombing of Iran aimed chiefly to prevent an Israeli nuclear strike, with Tehran forewarned so it could remove personnel and critical nuclear material beforehand.
• The power structure in Kiev is showing signs of breakup, evidenced by former foreign minister Kuleba fleeing by stealth across the border just after Zelensky barred diplomats and former diplomats from leaving the country.
• The Kremlin is closely tracking political collapse in Western Europe, including the fall of the Macron-aligned Bayrou government after it lost a confidence vote, feeding both military and political developments to the public via state television.

Questions & Answers

Q: Is Ukraine’s military nearing collapse?

Doctorow says Ukraine is suffering disastrous losses across the Donbas, particularly in Donetsk, as well as in Zaporizhzhia and Kherson. Ukrainian forces are withdrawing under Russian pressure, but he distinguishes these setbacks from the army being completely wiped out.

Q: Why does Doctorow believe Russia is advancing slowly in Ukraine?

Doctorow gives credence to the interpretation that Russia advances, stops, and draws Ukrainian forces into counterattacks where they suffer severe losses. Under this interpretation, Russia prioritizes destroying Ukrainian manpower over rapidly pursuing retreating forces.

Q: Does Doctorow expect Russia to advance beyond the Dnieper River?

Doctorow says Russia has no plans to advance beyond the Dnieper River. He nevertheless says Russia may seize Odessa and large parts of other oblasts, which he distinguishes from eliminating the Ukrainian army entirely.

Q: What signs of political instability in Kiev does Doctorow identify?

Doctorow points to former foreign minister Kuleba crossing the border by stealth and reaching Lviv. He says this happened shortly after Zelensky barred diplomats and former diplomats from leaving Ukraine, interpreting it as a sign that Kiev’s power structure is breaking up.

Q: What happened to the Hamas negotiators in Doha, Qatar?

The interview reports that the Israeli Defense Forces attacked Hamas negotiators as they approached a negotiating session in Doha concerning Trump’s proposals to end military activity in Gaza. The reported attack killed 37 people.

Q: Why does Doctorow consider the United States complicit in the Doha attack?

Doctorow argues that the United States controls Qatari airspace and therefore would have known about Israeli jets or missiles entering it. He concludes that Israel needed and received US permission, while the United States also knew the negotiators had been brought to the site.

Q: What does Doctorow say was the chief purpose of the US bombing of Iran in June?

Citing a European parliamentary source, Doctorow says the chief purpose was to prevent an independent Israeli nuclear strike on Iranian sites. He says Washington communicated with Tehran beforehand, allowing Iran time to remove personnel and critical material before the US bombing.

Q: How did Qatar respond to the Israeli attack in Doha?

Qatar’s foreign minister condemned the attack on residential buildings housing members of Hamas’s political bureau as a violation of international laws and a threat to Qatar’s security and sovereignty. Doctorow notes that the statement did not condemn the United States, which he attributes to Qatar’s position as a small regional power.

Summary & Key Takeaways

• Judge Andrew Napolitano interviews Professor Gilbert Doctorow on September 9th, 2025, opening with breaking news that the IDF attacked Hamas negotiators in Doha, Qatar, killing 37 who were about to address Trump's Gaza ceasefire proposals. Doctorow argues the US is complicit because it controls Qatari airspace and would have known about the strike.

• Doctorow relays a European parliamentarian's interpretation that Trump's June bombing of Iran was designed chiefly to prevent an independent Israeli nuclear strike on Iranian sites. Under this reading, the US communicated with Tehran beforehand, giving Iran time to remove personnel and critical nuclear material before the American bombs fell.

• On Ukraine, Doctorow says the military is suffering disastrous, politically sensitive losses across the Donbas and neighboring oblasts, withdrawing under pressure though not yet collapsed. Russia advances methodically, stopping to bait and slaughter Ukrainian counterattacks, seeking to destroy manpower and avoid another war for a generation.