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Sen. Tim Kaine dropped Vladimir Putin’s name more than 20 times in last night’s vice-presidential debate, suggesting that Gov. Mike Pence and his running mate, Donald Trump, shared an unseemly admiration for the Russian president. “You guys love Russia… You both have said Vladimir Putin is a better leader than the president,” Kaine said, referring to recent statements by both Republicans that contrasted Putin’s supposed strength with President Barack Obama’s weakness. Pence pushed back, calling Putin “small and bullying,” and saying that a Trump administration would respond to Russian provocation “with strong, broad-shouldered American leadership.”

The larger context for Kaine’s not-so-subtle attacks is Trump’s very public, largely one-sided relationship with Putin, which has often blurred the line between holding up Putin as Obama’s foil and starry-eyed fanboydom. Here’s a timeline of the ups and downs of the Trump-Putin bromance, which blossomed over the past few years as American-Russian relations frayed.

October 2007: Five months after Russia is accused of unleashing a cyberwar on the small Baltic country of Estonia, Trump tells Larry King that Putin is doing a great job: “Look at Putin—what he’s doing with Russia—I mean, you know, what’s going on over there. I mean this guy has done—whether you like him or don’t like him—he’s doing a great job in rebuilding the image of Russia and also rebuilding Russia period.”

“I have no relationship with [Putin] other than he called me a genius.”

2008: Donald Trump Jr. tells a real estate conference, “Russians make up a pretty disproportionate cross-section of a lot of our assets.…We see a lot of money pouring in from Russia.”

December 2011: In his book Time to Get Tough, Trump praises Putin while deriding Obama’s inability to contain him: “Putin has big plans for Russia. He wants to edge out its neighbors so that Russia can dominate oil supplies to all of Europe. Putin has also announced his grand vision: the creation of a ‘Eurasian Union’ made up of former Soviet nations that can dominate the region. I respect Putin and the Russians but cannot believe our leader allows them to get away with so much…Hats off to the Russians…Obama’s plan to have Russia stand up to Iran was a horrible failure that turned America into a laughingstock.”

June 2012: As President Obama meets with Putin, Trump tweets, “Putin has no respect for our President — really bad body language.”

June 2013: Shortly after Russia passes anti-gay laws banning gay “propaganda,” Trump tweets: “Do you think Putin will be going to The Miss Universe Pageant in November in Moscow—if so, will he become my new best friend?”

Do you think Putin will be going to The Miss Universe Pageant in November in Moscow – if so, will he become my new best friend? — Donald J. Trump (@realDonaldTrump) June 19, 2013

March 2014: At the Conservative Political Action Conference, Trump boasts, “I was in Moscow a couple of months ago, I own the Miss Universe Pageant and they treated me so great. Putin even sent me a present, a beautiful present.” Just after Russia annexes Crimea from Ukraine, Trump tweets, “I believe Putin will continue to re-build the Russian Empire. He has zero respect for Obama or the U.S.!” Also: “Putin has become a big hero in Russia with an all time high popularity. Obama, on the other hand, has fallen to his lowest ever numbers. SAD”

April 2014: Doubling down on his earlier tweet, Trump casts Obama as a weakling compared to Putin: “America is at a great disadvantage. Putin is ex-KGB, Obama is a community organizer. Unfair.” NATO had just condemned Russia’s “illegal intervention” in Ukraine.

America is at a great disadvantage. Putin is ex-KGB, Obama is a community organizer. Unfair. — Donald J. Trump (@realDonaldTrump) April 17, 2014

May 2014: Speaking at the National Press Club, Trump says he’s kinda sorta spoken with Putin: “I was in Russia, I was in Moscow recently and I spoke, indirectly and directly, with President Putin, who could not have been nicer, and we had a tremendous success.”

July 2015: Now the Republican presidential front-runner, Trump says he’d “get along very well” with the Russian president during an interview with reporters in Scotland. “I just think so. People say, ‘What do you mean?’ I think I would get along well with him.” He adds: “He hates Obama, Obama hates him. We have unbelievably bad relationships. Hillary Clinton was secretary of state. She was the worst secretary of state in the history of our country. The world blew apart during her reign. Now she wants to be president.”

October 2015: On CBS’ Face the Nation, Trump talks about sharing air time with Putin on a 60 Minutes episode: “I think the biggest thing we have is that we were on 60 Minutes together and we had fantastic ratings. One of your best-rated shows in a long time. So that was good, right? So we were stablemates.” (Trump and Putin were on different continents, were interviewed separately, and according Time, the ratings weren’t all that great.) Less than two weeks earlier, Russia had launched its first airstrikes in Syria in support of the Assad regime.

Despite overwhelming evidence to the contrary, Trump insists that there isn’t enough proof to point to pro-Russian separatists for shooting down a Malaysian Airlines flight over eastern Ukraine in the summer of 2014. “They say it wasn’t them,” he says. “It may have been their weapon, but they didn’t use it, they didn’t fire it, they even said the other side fired it to blame them. I mean to be honest with you, you’ll probably never know for sure.”

November 2015: During a Republican debate, Trump gets back in the barn with Putin: “I got to know him very well because we were both on 60 Minutes, we were stablemates, and we did very well that night.”

December 17, 2015: In a rare moment of recognition, Putin praises Trump, saying that he is “a very lively man, talented without doubt,” adding that Trump is the “absolute leader in the presidential race.” Before the day ends, Trump returns the favor. “It is always a great honor to be so nicely complimented by a man so highly respected within his own country and beyond,” he says of Putin.

“I got to know [Putin] very well because we were both on 60 Minutes…and we did very well that night.”

December 18, 2015: On Morning Joe, Trump defends Putin from allegations that he’s murdered journalists and political opponents. “He’s running his country, and at least he’s a leader. Unlike what we have in this country.” He adds, “I think our country does plenty of killing, also, Joe.”

February 17, 2016: At a rally in South Carolina, Trump inserts a little distance between himself and Putin. “I have no relationship with him other than he called me a genius. He said Donald Trump is a genius and he is going to be the leader of the party and he’s going to be the leader of the world or something.” (The word “genius” was Trump’s, not Putin’s.)

April 28, 2016: After Bill O’Reilly asks whether he and Putin would get along well, Trump responds, “Maybe we will, maybe we won’t. If we can make a great deal for our country and get along with Russia, that would be a tremendous thing. I would love to try it.”

June 17, 2016: Once again, Putin compliments Trump, calling him a “bright” person. On the same day, Russia bombs American-backed rebels in Syria.

July 25, 2016: After Democratic National Committee emails are leaked by WikiLeaks, Trump takes to Twitter to suggest the Russians were behind the hack because Putin “likes” him.

The new joke in town is that Russia leaked the disastrous DNC e-mails, which should never have been written (stupid), because Putin likes me — Donald J. Trump (@realDonaldTrump) July 25, 2016

July 27, 2016: Still gleeful over the DNC hack, Trump calls on Moscow to hack Hillary Clinton’s email. “Russia, if you’re listening, I hope you’re able to find the 30,000 emails that are missing,” he says during a news conference. “I think you will probably be rewarded mightily by our press.” He then declares, “I never met Putin. I don’t know who Putin is. He said one nice thing about me. He said I’m a genius. I said, ‘Thank you very much’ to the newspaper, and that was the end of it. I never met Putin.” Trump says he’d be firm with Putin, but also refuses to tell him to stay out of the presidential election: “I’m not going to tell Putin what to do. Why should I tell Putin what to do?”

“I was in Moscow a couple of months ago…Putin even sent me a present, a beautiful present.”

August 1, 2016: In an interview with ABC’s George Stephanopoulos, Trump claims that Russia isn’t going to take military action in Ukraine—despite having already done so. “He’s not going into Ukraine, okay, just so you understand. He’s not going to go into Ukraine, all right? You can mark it down. You can put it down. You can take it anywhere you want.”

September 8, 2016: At a national security forum hosted by Matt Lauer, Trump says the Russian president “has been a leader far more than our president has been.”

September 14, 2016: Perhaps forgetting his August statement that Russia wouldn’t go into Ukraine, Trump tweets about Russia’s annexation of Crimea: “Russia took Crimea during the so-called Obama years. Who wouldn’t know this and why does Obama get a free pass?”

September 19, 2016: Russia allegedly bombs a United Nations aid convoy outside besieged Syrian city of Aleppo, dashing hopes of reestablishing a US-Russia brokered ceasefire.

October 4, 2016: During the vice presidential debate, Trump tweets a link to a campaign press release titled, “Clinton’s Close Ties To Putin Deserve Scrutiny.”