In 2009, a fresh-faced Obama had just become president of the United States, while Putin — having already served his constitutionally limited two consecutive terms as president — had settled into a new role as prime minister of Russia.
Although officially Putin was no longer the most important politician in Russia, Obama seemed keen to meet him. He traveled to Putin's residence outside Moscow to talk, with a planned discussion of an hour and a half running over by a half-hour. The pair were photographed enjoying tea and pastries in Putin's garden.
“I found him to be tough, smart, shrewd, very unsentimental, very pragmatic," Obama said after the meeting. "And on areas where we disagree, like Georgia, I don’t anticipate a meeting of the minds anytime soon.”
2012 – Another two-hour meeting in Mexico
Obama seemed to have a relatively easy relationship with Dmitry Medvedev, Putin's successor as Russian president — the pair even went for burgers together in Arlington.
However, by 2012, Putin was president again.
The two met in person for the first time as presidents on the sidelines of the Group of 20 economic summit in San Jose del Cabo, Mexico. They talked for two hours, with almost a third of their discussion centered on the conflict in Syria, which had begun the previous year. Administration officials described the conversation as fruitful, but things soon went downhill.
2013 – An awkward photo, a canceled meeting and a 20- to 30-minute private talk
In 2013, Putin and Obama met on the fringes of the Group of Eight summit in Northern Ireland — a subsequent photo-shoot produced one of the most notorious images of the pair, with both men evidently unable to hide their frustration with the other.
That frustration was real: Obama and other members of the G-8 wanted to call on Syrian President Bashar al-Assad to step down to end fighting in the country, but Putin's support for Assad derailed this plan. As Reuters described it, the meeting between the two was "testy."
Shortly after the meeting, Obama announced that an upcoming summit with Putin, to be held in Moscow ahead of a Group of 20 meeting in St. Petersburg, had been canceled. Many linked the decision to Russia's move to allow former U.S. National Security Agency contractor Edward Snowden to stay in the country.
In the end, the pair did meet in St. Petersburg. Reports said they spoke privately for about 20 to 30 minutes in the corner of the room while the rest of the guests watched. Syria was again said to take up the majority of the conversation.
2014 – A 15-minute conversation during the D-Day commemoration in France
After a comically awkward meeting on a big screen, Obama and Putin had a real face-to-face meeting on the sidelines of a D-Day lunch in Colleville-sur-Mer, France. The pair broke away from the crowd and spent about 15 minutes talking about Ukraine.
"It's a positive thing that they spoke, but more needs to be done," an official told CNN after the talk.
2014 – A brief talk in Beijing
At APEC summit events in Beijing last year, the two men again broke away to talk privately a number of times. "On three occasions throughout the day, for a total of approximately 15-20 minutes, President Obama had an opportunity to speak with President Putin," White House spokeswoman Bernadette Meehan told reporters. "Their conversations covered Iran, Syria and Ukraine."
According to Reuters's Matt Spetalnick, reporters overheard a snippet of conversation between the two as the summit opened in a convention center outside Beijing. "It's beautiful, isn't it?" Putin was heard to have said in English, referencing the grand room the two men were in.
"Yes," Obama responded.
2015 – A tense toast in New York
The two met again on Sept. 28 at a luncheon hosted by U.N. Secretary General Ban Ki-moon during the U.N. General Assembly gathering in New York. And it seemed, well, tense.
Perhaps with good reason. During his address, Obama called out Russia's backing of separatists in eastern Ukraine as well as its military intervention in Syria, where the war is grinding into a fifth year. Putin claimed that the West was responsible for the chaos in the Middle East and North Africa. As my colleague Ishaan Tharoor noted, "He asked 'those responsible' (presumably the U.S.): 'Do you know what you've done?'"
The luncheon was a precursor to a longer one-on-one talk later in the day before Putin left for Moscow.
2015 – A behind-closed-doors chat in Paris
Putin isn't even looking this time, but the handshake certainly appears firm.
The leaders met Nov. 30 on the sidelines of the big climate change conference in Paris. It was their second face-to-face meeting in two weeks, after a small group session during the G-20 summit in Turkey. Dmitry Peskov, the Kremlin spokesman, was quoted by RT as saying that Monday's discussion — which lasted about 30 minutes — was "eventful."
Among the topics mentioned, Peskov said, were movements toward a political resolution in Syria and the need to target the Islamic State, rather than militant groups that oppose Russian ally Assad; the conflict in eastern Ukraine; and Turkey's downing of a Russian military jet over the Syrian border last week.
Peskov said Obama "expressed regret" over the warplane incident, which has strained ties between Russia and Turkey, exposing the possibility of more conflict between foreign powers operating in Syria.