Fiona Hill says Putin 'doesn't think anything has gone wrong' in Ukraine and lives 'in a bubble'

• The conflict in Ukraine has been devastating for Russia, but Putin doesn't think it's going poorly, Fiona Hill says.
• The Russian leader has received poor intelligence and lives "in a bubble," according to the Russia expert.

The war in Ukraine has so far been disastrous for the Russian military on multiple levels, but Russian President Vladimir Putin "doesn't think anything has gone wrong," according to a top Russia expert.

"The sad fact of the matter from our perspective is that Putin doesn't think anything has gone wrong. I know that might sound absolutely bizarre, because we can say that if he declares victory now it's very much a Pyrrhic victory," Fiona Hill, who served as the top Russia advisor on the National Security Council under the Trump administration, said Tuesday at an event held by the Chicago Council on Global Affairs.

Though the war has been "devastating for Russia," Hill said that Putin's mentality is still shaped by his time as a KGB operative, and he always looks to adapt to the situation on the ground in order to achieve his goals. The Russian leader knows that when operations don't go as planned, then "you have to have contingencies," she said.

"As far as Putin is concerned he'll find a way to still meet" his goals in the war, which include the "dismemberment" of Ukraine, she added. Hill underscored that the Russian leader doesn't see Ukraine as a real country, viewing it instead as territory that historically belongs to Russia.

Putin effectively perceives himself as carrying on the legacy of the Russian tsars or emperors, Hill said, and subjugating Ukraine is a crucial part of this in his eyes.

"This is a war about history. Basically, Vladimir Putin has invaded Ukraine because Ukraine has not comported with his view of Russian history," Hill said. "He sees himself as a tsar, he sees himself as reclaiming and regaining Russia," she went on to say.

Russia has lost thousands of soldiers in Ukraine, as well as an astonishing number of generals, since Putin, without provocation, launched the war in late February. The Russian military failed to take Kyiv, and it has struggled to make progress in other areas of strategic significance over the course of the conflict. The war has led to unprecedented sanctions and unified the West in major ways, pushing the historically neutral countries Sweden and Finland into the arms of NATO — a military alliance Putin has railed against for years and partly blamed for the Ukraine invasion.

When asked why Putin miscalculated so badly, Hill pointed to a number of factors. The COVID-19 pandemic saw Putin end up in "more isolation than normal" over the past couple of years, Hill said, emphasizing that the whole world has been impacted by this.

Putin also didn't receive solid intelligence on Ukraine for a "variety of structural reasons," Hill said, including "the very high penalty of getting things wrong." People who have displeased the Russian leader have often ended up in prison or died in violent and suspicious ways.

Additionally, Putin thought West was going through a "period of incredible weakness," Hill said, which wasn't entirely wrong in the sense that the US and Europe have both struggled with major political divisions in recent years. But the war backfired in this regard and has seen the West rally together to support Ukraine and counter Russia.

Putin also "doesn't understand Ukraine" and believes it "belongs to Russia," Hill said, and he underestimated the sense of citizenship that's emerged in the former Soviet republic over the past 30 years. The Russian leader thought that this war would be a "replay" of successful Soviet incursions into Eastern European countries during the Cold War, as well as the annexation of Crimea in 2014, because "he's in a bubble," Hill said.