On Sunday, The New York Times revealed that Obama made a variety of bizarre assertions in private meetings with those he relies on to influence his reasoning on national security policy.

The article in The Times gave readers a window into Obama’s thought process relating to the politics and strategy associated with the likely years-long campaign aimed at defanging the ISIS threat. In The Times, Obama was quoted mocking his political opponents who regard him as “professorial” and expressing his frustrations with foreign allies and adversaries alike.

The president apparently impressed those with whom he has spent time discussing matters relating to national security, but it is unclear why that would be. Obama’s quotes leave the reader with the impression that he does not understand the enemy’s thinking and he doesn’t really care to try and understand it.

For instance, The Times noted that Obama believes that by merely aggravating the United States and provoking it into armed conflict, the Islamic State has already committed a fatal error.

But the president said he had already been headed toward a military response before the men’s deaths. He added that ISIS had made a major strategic error by killing them because the anger it generated resulted in the American public’s quickly backing military action.

If he had been “an adviser to ISIS,” Mr. Obama added, he would not have killed the hostages but released them and pinned notes on their chests saying, “Stay out of here; this is none of your business.” Such a move, he speculated, might have undercut support for military intervention.

There is scant evidence to suggest that merely going to war with the United States is a tactical error. Only in rare moments when the American people are asked to commit to total war with a difficult but nevertheless circumspect objective can it honestly be considered an unequivocal mistake for an adversary to take on the United States in an asymmetrical contest. Wondering why ISIS did not avoid going to war with America presupposes they do not want a war with America.

National Review’s Jim Geraghty has a good take on Obama’s thinking. “Notice Obama’s assessment presumes ISIS wants to avoid a U.S. military intervention,” he wrote. “Is this a manifestation of the mirroring effect, where Obama projects its own values and priorities onto its foes? (Think about how often he insists publicly that seizing Crimea and moving into Ukraine isn’t in Russia’s interest, or that bellicose or provocative actions on the part of Iran aren’t in that country’s interest.)”

ISIS appears to want to send the message, far and wide, that they don’t fear a clash with the U.S. military. Perhaps they want to demonstrate that they can commit horrific crimes against American civilians with no serious repercussion. Maybe they think God wants them to do this. Maybe they’re nuts! In the end, the “why” matters less than the “what.”

Is Geraghty right? That is surely debatable, but at least his is an effort to get into the enemy’s head and make an assumption about their motives. Instead, Obama seeks to identify the actions ISIS should have taken if it were a Western non-governmental organization with a fundraising problem.

It is not hard to envision a scenario in which going to war with the United States ends up seeming like the best idea ISIS ever had. There is no better fundraising and recruiting tool than to attack, and be attacked, by the United States. The Islamic State is embedded in civilian population centers and, if America incurs collateral damage during this campaign, America’s adversaries will exploit it. What if the air war fails to degrade ISIS, but the Islamic State gains support across the Sunni world over the course of that campaign? Would they have made a mistake in goading America into a war?

Pulling unwilling actors into a conflict is a strategy in itself, one the Islamic State already practices. ISIS seeks to exacerbate the Sunni-Shia divide. By forcing Iran to commit troops to Iraq to fight the Islamic State, ISIS has already enjoyed a major victory and it was secured by only drawing a combatant into the war.

Moreover, no one can define what success in this fight would look like. Is it the recapturing of territory in Syria and Iraq? If so, which militia will serve as an occupying force? Is it decapitating ISIS’s leadership? If this cannot be accomplished from the air, see question one.

Does the president really not have any desire to understand ISIS? It is hard to say, but Obama’s comments about advising the Islamic State are disturbing. Obama reflected a similar lack of understanding when he mocked Vladimir Putin for his gambit in Ukraine.

Mr. Obama was relaxed enough, as he discussed the array of foreign policy crises facing him, that at one point he ridiculed President Vladimir V. Putin’s rationale for intervening in Ukraine to protect Russian speakers by saying the United States should intervene in Mexico to protect enclaves of Americans. When a writer jokingly asked if he was announcing plans to invade Mexico, he laughed and said no, Canada, because it has more oil.

Did I miss the report indicating Putin went to war in Ukraine for resources? Was the Russian naval base at Sevastopol in any danger? If anything, Crimea is a drain on Russian resources, and annexing it forced Moscow to contemplate either a massive infrastructure project or a wider war in Ukraine to connect the peninsula to mainland Russia. The Kremlin adopted a bit of a dual strategy aimed at securing the goal of integrating Crimea into Russia proper.

Putin did not go to war in Ukraine for energy. He went to war in Ukraine for a naked, raw power. He went to war in Europe to show the Western powers the limits of Russian patience. While Putin woke the sleeping NATO giant for now, it has yet to be demonstrated that this comfortable and weak alliance of democracies would truly go to war with Russia over a few miles of territory on Estonia’s border.

Obama’s allies are not fools. They make reasoned calculations just as does the president. If The Times’ account is to be believed, Obama doesn’t care to understand his enemy’s thinking – he views his own thought processes as superior. That is truly disheartening.