Vladimir Putin seized the Crimean Peninsula to test the West's resolve and got away with it, dismissing Obama's economic sanctions as meaningless. Emboldened by how easy it was, he sent forces deeper into Ukrainian territory last summer, bragging he could take over the country if he wanted.
The poorly equipped Ukrainian army was no match for the armed-to-the-teeth, Russian-backed rebels. The Ukrainian government needs anti-tank weapons and other arms from the U.S. But Obama resisted, saying he preferred a softer, kinder, diplomatic approach to dealing with Moscow.
This must have elicited a big laugh in the Kremlin, where Putin was calling the shots, while Obama dilly-dallied over how to respond to the worst military crisis in Europe since the Cold War.
As Russian-led forces seized more ground, there were growing calls for Obama to come to Ukraine's aid in its desperate hour of need. In August, Arizona Sen. John McCain went on "Face the Nation" to urge Obama to arm the Ukrainians, "for God's sake."
Flash forward to 2015, when Obama still refuses to give the Ukrainians the arms to defend themselves from Putin's naked aggression.
At a news conference here this week after meeting with German Chancellor Angela Merkel, Obama indicated that he hasn't budged on the issue one iota. Though he insists he's still studying the problem, he clings to the naive hope that somehow a peaceful deal can be worked out with the brutal former KGB agent.
But if it can't, then what?
"If, in fact, diplomacy fails, what I've asked my team to do is look at all the options -- what other means can we put in place to change Mr. Putin's calculus -- and the possibility of lethal defensive weapons is one of those options that's being examined," he said.
Just in case someone might mistakenly get the idea that he was actually nearing a decision, Obama added this:
"I want to emphasize that a decision has not yet been made." No kidding?
As we learned from the fat tell-all books written by his first two secretaries of Defense, Obama obviously has a hard time making up his mind on critical national security issues. Both Robert Gates and Leon Panetta admitted to being frustrated by Obama's procrastinating, and complained that swift, decisive, military leadership was not his strong suit.
He certainly wasn't in any hurry to respond to the lethal threat posed by the reinforced ISIS and al-Qaeda terrorist armies that seized large swaths of territory in Syria, Iraq, Afghanistan and elsewhere in the Middle East and across North Africa. He had won a second term by telling voters that he had crushed terrorism, that al-Qaeda's leadership had been "decimated," and that he had the terrorists "on the run."
Since then, however, he's learned that no such thing ever happened. Al-Qaeda terrorists had metastasized into a far more deadly army that had rolled across Iraq to the gates of Baghdad, seized parts of Syria and spread across North Africa.
As their blood-soaked reign of terror shocked the world, Obama resisted calls for a U.S. bombing campaign. When the mass executions and beheadings forced his hand, the bombings did begin, but without the strategic impact that had been hoped for.
Obama has been criticized for "leading from behind," and in the war on terrorism, that's been the case for a long time. In Iraq, it looks like a case of too little, too late. In Syria, the bombings have not tamed the Islamic State's well-financed armies, just sent them into hiding or into adjoining countries -- biding their time for the next offensives.
"You're not going to win this just with airstrikes," a U.S. official in Baghdad said this week.
Elsewhere, the U.S. was in retreat. Shiite rebels have seized control of the government of Yemen, and the State Department said it was shutting its embassy there because it's too dangerous. The West Wing doesn't want another Benghazi.
Meantime, long after ISIS rampaged across the region, Obama belatedly sent a formal request to Capitol Hill Wednesday, seeking authority for the use of military force against the Islamic State's armies.
But Obama's late legislative gambit has other objectives in mind. The war-making authority he presumably wants would continue the U.S. air strikes and military training of local forces in Iraq and Syria -- authority he already has under existing law.
A troublesome new provision, though, would prohibit "enduring offensive ground combat operations." But why send this signal to an enemy that is in this war for the long duration?
Rep. Adam B. Schiff, Democrat of California, who has offered his own authorization bill, may have inadvertently explained the real purpose behind Obama's proposal:
"This is not going to be a war-strategy document," he told military analyst Karen DeYoung, "it's going to be a checks-and-balances document that sets congressional limits on what we want our president to be doing."
It's likely that debate over new war-making authority, to replace George W. Bush's 2002 authorization, will last well into this year, but without Obama's time restrictions.
Meanwhile, it is clear by now that Obama's prosecution of the war, in the beginning, was all about rapid withdrawal -- especially in Iraq. That led to the Islamic State's brutal, unimpeded military conquests across the region and a far more serious terrorist threat in Europe and, possibly, here at home.
Clearly, the president's war strategies are not working. This week, it was reported that the White House was considering "slowing its planned withdrawal from Afghanistan for the second time."
As for Obama's reluctance to arm Ukraine, there's a line of high-level Democrats who are now urging him to do just that, including Ashton Carter, his choice to be the new secretary of Defense.