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If United States President Donald Trump wants to make progress in negotiations with Russian President Vladimir Putin, he needs to put Tomahawk missiles back on the table for Ukraine instead of just fiddling with sanctions, according to Mikhail Khodorkovsky, a major Russian opposition figure with deep knowledge of the Kremlin.

Khodorkovsky, once the richest of the Russian oligarchs, jailed for 10 years and now in exile in London, said in an interview with the Washington Post that Putin is unlikely to be strong-armed by new sanctions against big Russian oil companies.

Trump, who campaigned for president claiming he could end Russia’s war in Ukraine in just 24 hours, has embarked on a dramatically different approach to dealing with Putin than his predecessors in the White House who sought to isolate or sideline the Russian leader.

Trump invited Putin to a summit in Alaska, speaks with him regularly and often talks about the prospects of lucrative bilateral trade.

In recent days though, relations between the men seem to have soured.

Expressing frustration with Putin over Ukraine, the Trump Administration briefly contemplated supplying Ukraine with Tomahawk cruise missiles and then scrapped a planned summit in Budapest and imposed US sanctions on the oil companies, Rosneft and Lukoil.

The sanctions were Trump’s first punitive action against Russia since returning to the White House despite Putin for months resisting the American President’s demands for a ceasefire in Ukraine.

“I think when Trump started with a position of the good cop, that was a good approach but after being a good cop, he should have shown the other side,” Khodorkovsky said in the interview, at his office in central London where he leads and finances an opposition coalition.

“The Tomahawks were a strong threat whereas the sanctions against Rosneft and Lukoil are too weak.”

The key to dealing with Russia is understanding Putin and his paramount role in the country, Khodorkovsky said.

He explained that the Russian leader is the main driver of the war - in contrast to the elites around him or the generals - and has a paranoid outlook.

The only way of putting pressure on Putin is to threaten force, Khodorkovsky said.

“You are actually dealing with a thug,” he said.

“Mentally this person has got used to living in the world where there is no rule of law, no law,” he continued, referring to Putin’s background in Russia’s intelligence services.

“He has worked in all these organisations where force was the only language,” he added. “So you can’t just go and say to them, ‘I’m going to make you a really good offer.’”

Russian oligarch, prisoner, and now exiled regime critic Mikhail Khodorkovsky. Photo / Getty Images

Trump’s weeks-long flirtation with supplying Tomahawks to Ukraine appeared to deeply trouble the Kremlin.

It prompted numerous alarmed statements and public warnings from Russian officials, until Putin appeared to convince Trump in a phone conversation last week to drop the idea.

Khodorkovsky said threatening to send Tomahawks was so effective because that kind of weapon, with a range that could easily reach Moscow, potentially poses a direct threat to Putin himself.

Khodorkovsky noted that Israel had decimated the leadership of its enemies with such missiles.

“Basically, it was like saying, ‘I’m going to declare a hunt against you and your entourage, your inner circle,’ because I understand the attitude of the Kremlin to it.”

The sanctions, by contrast, “sounds like I’m just going to step on your shoe”.

As Khodorkovsky spoke to the Post, Putin said the new sanctions would not significantly damage Russia’s economy.

“The new US sanctions are an attempt to put pressure on Russia,” he said. “No self-respecting country ever does anything under pressure.”

Putin also said that any use of Western long-range weapons against Russia would be met with a “serious if not overwhelming” response.

The Russian leader appears to be concerned about Khodorkovsky and his efforts to co-ordinate an opposition movement. After more than 10 years in exile, following Khodorkovsky’s surprise pardon and release from prison, Russia’s domestic security service, the FSB, last week abruptly opened a criminal investigation into him and members of the Russian Anti-War Committee that he helped found, accusing them of seeking to foment a coup in Russia.

Khodorkovsky believes the trigger was a decision by the Parliamentary Assembly of the Council of Europe two weeks earlier to set up a platform of dialogue with the group, granting it important international legitimacy and suggesting that Russia’s notoriously fractious opposition could unite.

“Since the year 2000 until today, the policy of the presidential office has always been to stop the opposition from consolidating,” Khodorkovsky said.

“Now we have the platform created by the Parliamentary Assembly of the Council of Europe, demonstrating that in fact a considerable part of the Russian opposition has now learned how to unite.”

The FSB case described the dialogue platform as an attempt to form a “constituent assembly of the transition period and an alternative to the authorities of the Russian Federation”.

Khodorkovsky said he believes that for Putin, official recognition in Europe of a significant part of the Russian opposition at the same time that the US was talking about supplying Tomahawks could not be coincidental.

“The Kremlin thinks in terms of myths, perhaps conspiracies, and they don’t think there are any accidental things happening at all,” he said.

“They basically think that Tomahawks, the parliamentary assembly, something else happening are all kind of links in the chain.”

Khodorkovsky said he believes the case against him suggests the Kremlin is growing nervous.

“It’s weird, I think that there’s no explanation other than they are really worried that there’s going to be an imminent transition of power,” he said.

“The majority that Putin enjoys today would collapse the moment the power transition starts.”

Khodorkovsky was once intimately familiar with the highest levels of power in Russia.

He was a leading member of the Komsomol, the Communist youth organisation, and one of the first to be awarded permission to dabble in entrepreneurial activities allowed under the perestroika reforms that helped speed the Soviet collapse.

He rapidly amassed a fortune in the free-for-all privatisations of the 1990s, becoming Russia’s richest man by the early years of Putin’s presidency.

Khodorkovsky had close contacts with government officials but ultimately refused to the toe the Kremlin line.

His fall was even more dramatic than his rise and he became a symbol of Putin’s intent to curb oligarchic power.

Khodorkovsky was accused of fraud, stripped of his Yukos oil empire - which was taken over by state-owned Rosneft now being targeted by sanctions - and imprisoned.

In 2013, ahead of Russia’s showcase Sochi Winter Olympics, he was pardoned by Putin on the agreement that he leave the country and not engage in politics.

He has since become a key figure in the opposition, in some cases financing it with the remnants of his personal wealth but also seeking to unite its often warring factions.

The Anti-Corruption Foundation, of the late opposition leader Alexei Navalny, who died in a Russian prison, however, has refused to join.

Putin’s worries, Khodorkovsky said, are driven in part by the country’s deteriorating economic situation after nearly four years of war.

While the sanctions aren’t sufficient to cripple Russia’s economy, he said, Putin is running out of time.

He has been squeezing the middle class with taxes and inflation while spending massive amounts to recruit soldiers and power the factories making war materials, Khodorkovsky said.

“He can spend what he spends today but he can’t increase it,” he said.

“As soon as he starts increasing the war spending, he will run into problems in society. … The middle class has been squeezed dry.”

Ultimately, however, it all comes back to Putin himself, said Khodorkovsky.

He has been advising Western leaders that if they want to end the war, focus their strategies on Putin, who is “the axis, the pivotal points of this war because his inner circle, none of them really want the war”.

He said what made Trump’s talk of cruise missiles so effective is that Putin took it personally.

“What you have to do is create psychological problems for him,” he said, suggesting that the West create issues that require his personal attention. “Let him … spread himself thin.

“This is the problem of any totalitarian or authoritarian regime: It’s all tied to one person.

“If one person starts to get tired and begins to make mistakes, the whole system collapses,” he said.