“If Putin likes Donald Trump, I consider that an asset not a liability,” the incoming U.S. president said at a January 11 press conference, shortly before taking office. On Friday, he’ll get the chance to test that when he meets the Russian president for the first time at the G-20 summit in Germany. But other U.S. and European leaders who have sought to cultivate personal ties with the former KGB agent at the helm of Russia for the past 17 years have frequently found that that doesn’t always pay political dividends.
Here’s a quick guide to those who tried to do business with Putin, who failed—and some who succeeded.
George W. BushPresident of the United States 2001‑2009
Hopes After his first meeting with Putin in June 2001, Bush said he had got a “sense of his soul” and found him “straightforward and trustworthy” and a man “deeply committed to his country.”
Initial results Putin acquiesced to U.S. abrogation of 1972 Anti‑Ballistic Missile treaty and was the first foreign leader to call Bush after 9/11. Later, he allowed NATO to ship military equipment across Russian territory to Afghanistan.
How it turned out Bush’s view of Putin turned to bitter disillusionment after Putin invaded U.S. ally Georgia in August 2008.
Gerhard Schröder Chancellor of Germany 1998‑2005
Hopes Called Putin a “flawless democrat” in 2004.
Initial Results Cultivated ties with Putin, opposing the U.S.-led invasion of Iraq in 2003 and agreeing to build a new gas pipeline under the Baltic Sea from Russia to Germany.
How it turned out Schroeder took a job with Russian state gas exporter Gazprom soon after leaving office in 2005, sparking criticism. In April 2014, at the height of the Ukraine crisis, he was photographed in a bear hug with Putin as he arrived to celebrate his 70th birthday party in St. Petersburg.
Angela Merkel Chancellor of Germany 2005‑present
Hopes “I am convinced that we have the possibility of expanding our strategic partnership.”
— Jan. 16, 2006
Initial results Merkel hoped to do business with Putin while avoiding the close ties of her predecessor. She completed the Baltic pipeline, begun by Schroeder, carrying Russian gas directly to Germany. At its peak in 2013, trade between the two countries had nearly doubled since before she took office.
How it turned out The relationship soured sharply in 2014 as Merkel, feeling deceived by Putin over Ukraine, rallied Europe around sanctions against Russia. Germany’s intelligence chief has warned Russia may use cyber-attacks to influence the elections this year.
Emmanuel MacronPresident of France 2017‑present
Hopes “I want us to win the fight against terrorists in Syria and build together lasting political stability,” Macron said after their first meeting May 29. “We have laid the ground for that work together today. I believe we’ve had an extremely frank and direct exchange. We have told each other everything.”
Initial results Macron won praise at home when he confronted Putin at their joint appearance over what he called Russian “propaganda” efforts during the French election this year. Putin, uncharacteristically, didn’t fire back.
How it turned out So far, Macron's performance with Putin has helped the political newcomer show he's ready to play in the big leagues of world leaders. But who will get the best of the prickly Putin-Macron courtship remains to be seen.
Nicolas Sarkozy President of France 2007‑2012
Hopes Praised Putin as a pragmatist before they met in Moscow in 2007, saying this helped to find “a common language” on important international issues.
Initial results Sarkozy played the key role in brokering a cease-fire with Putin after Russia invaded Georgia, a diplomatic triumph for France. Big French companies like Renault landed major deals in Russia.
How it turned out Sarkozy, who failed in his bid to run again for the French presidency this spring, turned openly sympathetic to Putin in recent years, earning private audiences with Putin. His successor was left with the task of cancelling a major French arms deal struck by Sarkozy with Putin because of the Ukraine crisis.
Alexander Lukashenko President of Belarus 1994‑present
Hopes Joined with Russia in a union that makes the two countries closest allies, Lukashenko regularly praises Putin.
Initial results Lukashenko has managed to maintain a measure of independence, keeping billions in Russian energy and other subsidies that are vital to his Soviet-style economy. He played a major role as a mediator in talks that led to a peace deal in 2015 aimed at ending the war in eastern Ukraine.
How it turned out With Belarus sandwiched in between Russia and the West, Lukashenko has succeeded in finding a balancing act between the two. He has managed to win financing from both sides and maintained his 23‑year grip on power.
Viktor Yanukovych President of Ukraine 2010‑2014
Hopes Putin openly backed Yanukovych in his in 2004 presidential bid, which saw his initial election victory reversed by popular protests against widespread vote irregularities.
Initial results With help from Moscow, Yanukovych staged political comeback in 2010 and later won billions in Russian subsidies and other support for his government.
How it turned out An effort to balance between the West and Russia failed after Yanukovych abruptly pulled out of a deal with the EU in 2014, leading to his ouster by violent street protests. He’s now in exile in Russia.
Mikhail Khodorkovsky Exiled Russian businessman, philanthropist and former oligarch
Hopes Once Russia’s richest man and owner of Yukos Oil Co., Khodorkovsky pushed for greater political power by backing opposition and other parties.
Initial results Yukos became Russia’s largest oil company and Khodorkovsky was close to a deal to sell a large stake to Exxon in 2003.
How it turned out Khodorkovsky spent a decade in prison on tax-evasion and fraud charges he denounced as politically motivated. He was pardoned in 2013. From exile in London, Khodorkovsky is using what’s left of his fortune to finance civil-society projects and election monitoring aimed at securing Putin’s departure.
Mikhail Fridman Russian entrepreneur, business executive, and philanthropist
Hopes Sought and won Putin’s blessing for a $7 billion deal to create TNK-BP, an oil company jointly owned with BP plc, steering clear of politics to avoid Kremlin wrath.
Initial results TNK-BP became one of Russia’s biggest and most profitable oil companies and Fridman’s Alfa Group expanded its finance, telecom and retail businesses, making him one of the country’s richest men.
How it turned out Quite well for Fridman so far. He and his Russian partners were allowed to sell his stake in TNK-BP to the state oil company in 2013 for about $14 billion.
Barack ObamaPresident of the United States 2009‑2017
Hopes “My hope is, is that we can have a constructive relationship where, based on common respect and mutual interest, we can move forward.” — March 3, 2009
Initial results Under Obama’s “reset” policy, the U.S. and Russia in 2010 signed a landmark nuclear-arms-control treaty. Russia also agreed to allow the U.S. to expand shipments of military supplies to Afghanistan across its territory, a key U.S. priority.
How it turned out After Putin returned as president in 2012, ties worsened, culminating in Russia’s 2014 annexation of Crimea. Moscow in 2015 tore up the Afghanistan transit agreement and moved to prop up Syria’s Bashar al-Assad against U.S.-backed rebels. U.S. Intelligence agencies have found Putin approved hacking of the campaign of Hillary Clinton, whom Obama backed as his successor.