Today, as the Apprentice-host-turned-president gears up to meet with his ex-KGB Russian counterpart in Helsinki for their first summit, the world is asking a similar question.
Syria, election meddling and Ukraine will all be on the table in the talks, but much of the focus will be on the personal chemistry between the two men.
Trump has long expressed his admiration for the strongman leader, while US intelligence services allege Putin ordered Russian intervention to tip the 2016 US presidential election and push the brash billionaire into the White House.
In terms of temperament and style, the presidents could scarcely be more different.
While Trump speaks off the cuff and often angrily contradicts his own advisors — or himself — Putin is never caught off-guard in public and rarely raises more than an eyebrow to express his emotions.
Putin keeps up to date via thick folders of intelligence reports and press summaries, but Trump’s advisors reportedly struggle to get him to read even the shortest of briefings.
And whereas the US president throws his opinions out via social media, his opposite number in the Kremlin does not even own a smartphone — relying instead on domestic media to make his feelings known.
Mano-a-mano
But their differences will not necessarily prevent the pair from bonding.
“Putin has proven himself to be incredibly savvy at reading personalities and characters,” said Alina Polyakova, a foreign policy fellow at the Brookings Institution in Washington.
“This is what he was trained to do, after all, as an intelligence officer and I think he’s particularly been good at reading character weaknesses,” she told AFP.
“He will praise Trump and try to bond with him in sort of a mano-a-mano way. Trump will be responsive to that tack,” she added.
If this is the case, Putin will also have some genuine similarities to tap into.
The pair share authoritarian tendencies. After a recent meeting with North Korean dictator Kim Jong Un, Trump said he envied the way “his people sit up at attention” when he speaks and wished “my people” did the same.
They both prefer making surprise, unilateral decisions to getting bogged down in the business of dealing with institutions or checks and balances.
And the two men are nationalists who promised to make their countries “great again” — Putin after the instability that followed the collapse of the USSR and Trump after what he saw as the decline of American industry.
They are also both wealthy, even if they have different ways of showing it.
Documentaries on Russian state TV emphasise Putin’s ascetic lifestyle, but those in his inner circle have accumulated vast riches and critics say the president himself is worth tens of billions of dollars.
Trump, who uses a golden lift to get up to his New York apartment, is synonymous with ostentatious displays of wealth, though US media report he is worth billions less than he claims.
‘Hit first’
Putin was born into a working-class family in Leningrad — now Saint Petersburg — in 1952, before joining the KGB intelligence service in his 20s.
Trump was the fourth of five children born to a wealthy New York real estate developer. He later used what he called a “very small loan” of $1 million from his father to get started in the same business.
Published in Daily Times, July 16th 2018.
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