In the fall of 2007 I participated in a debate in New York on the question of whether Russia was again becoming an enemy of the United States. I argued it was.

"We worry about political trends within Russia," I said in my closing statement, "not just because we are friends of democracy, human rights, freedom, the rule of law, but also because the respect that governments have for their own people tend to correlate with their attitude and behavior vis-à-vis the outside world. We worry about Russian behavior toward countries like Ukraine, Estonia and Georgia because we fear that behavior is a harbinger for what's in store for Europe and the United States."

If you think I'm claiming vindication here, you would be right. But it wasn't as if it took great political acumen to come to such conclusions.

Vladimir Putin's first major act in power had been to lay waste to the city of Grozny in a manner reminiscent of Tamerlane. Next he went after his domestic opponents in show trials that recalled the methods of Andrey Vyshinsky. Soon he linked hands with Jacques Chirac of France and Gerhard Schröder of Germany to try to stop the Iraq war—which is to say, to keep Saddam Hussein in power. Then he supplied Iran with its first nuclear reactor.

In 2005 Mr. Putin called the collapse of the Soviet Union "the greatest geopolitical catastrophe" of the 20th century. In 2006 a mysterious pipeline explosion left Georgia without gas in the dead of winter, a tactic used against several of Russia's neighbors. Later that year came the murders of Anna Politkovskaya, a muckraking journalist, and Alexander Litvinenko, a Russian intelligence officer who had defected to Britain and was dispatched with a dose of polonium. A few months later Estonia, another free-world thorn in Russia's side, was subjected to a massive cyberattack.

This is only a partial list of the evidence available at the time of the debate. But it suggested a definite trend. The invasions of Georgia, Crimea and eastern Ukraine still lay in the future. So did the murder of Sergei Magnitsky, the prison sentences for Pussy Riot, the legal harassment of Alexei Navalny, the asylum granted to Ed Snowden, the cheating on the IMF Treaty.

And now the shooting down of Malaysia Airlines Flight 17 and the murder of its 298 passengers and crew, followed by the coverup. How do you "reset" that?

You don't. You can't. But you can at least try to figure out where you went wrong at the start.

Take Columbia University professor and Russia expert Robert Levgold, who took the opposite side in that 2007 debate. Russia, he argued, was not an enemy but "a challenge." The problem of Russian foreign policy wasn't so much its aggressive efforts to reconstitute the old Soviet sphere of influence, but rather its "ambiguity and shapelessness." U.S. policy should focus on "constructive and effective dialogue."

In a Foreign Affairs article in 2009, Mr. Levgold went a step further: "Too many Americans," he cautioned, "mistakenly believe that Russia's leaders are incorrigibly antidemocratic and bent on bludgeoning Russia's neighbors, blackmailing Europeans, and causing trouble for the United States." It was important, he added, to change the tone. "If the style and substance of Obama's foreign policy change as much as he and his team have suggested they will, the context for U.S. policy toward Russia will improve no matter what happens on the specific issues that set the two countries at odds."

By and large, the professor got exactly the policy he wanted. Yet the results were precisely the opposite of the ones he forecast.

U.S.-Russia relations were strained at the time of the debate. They are in shambles today. Mr. Obama's good will did not beget conciliation from Mr. Putin. It elicited contempt. A more cautious and less unilateral U.S. foreign policy did not turn Russia into a team player at the U.N. Security Council. It merely facilitated Russian obstructionism. Consistent attempts to de-escalate tensions over Ukraine, to offer Mr. Putin this or that off-ramp, did not induce better behavior. It signaled that the West lacked any will to stand in Russia's way.

There was no White House outrage when Russian separatists were shooting down Ukrainian aircraft in recent weeks. On the contrary, Mr. Obama was trying to ring-fence events in the region as "a quarrel in a far away country between people of whom we know nothing," as somebody once said.

Does it occur to anyone in the administration that U.S. efforts to play down events in eastern Ukraine contributed to the permissive environment in which Flight 17 was brought down?

Political shortsightedness being almost incurable, Mr. Legvold has taken to the pages of the current issue of Foreign Affairs to urge "damage control" in relations with Russia and to avoid "misperceptions." But the main misperception has been his—and the administration's—view of today's Russia. Too bad Vladimir Putin sees this White House exactly for what it is.