President Obama's remarks at Thursday's National Prayer Breakfast have ignited yet another firestorm on the right surrounding the president's eyebrow-raising bashing of the West's problematic past. In case you missed it, after criticizing ISIS, the president said: "And lest we get on our high horse and think this is unique to some other place — remember that during the Crusades and the Inquisition, people committed terrible deeds in the name of Christ."

Obama didn't stop with comparing today's jihadis to Christian sins of 800 to 1,000 years ago. "Slavery and Jim Crow all too often was justified in the name of Christ," Obama continued.

Both of these historical examples are very true. (Though Obama's comments do obscure the fact that it was Christian abolitionists, such as William Wilberforce, who helped lead the fight against the slave trade.) But they are the wrong parallels for the leader of the free world to draw — or at least, for this leader of the free world to draw.

Of course, there are many circumstances in which our leaders rightly hold us to a higher standard than our enemies. But Obama is, frankly, not the right messenger to deliver this lecture. As Juliet Eilperin notes in The Washington Post, "President Obama has never been one to go easy on America." He has downplayed "American exceptionalism," noting that other countries think they're special, too. He has suggested, as Eilperin continues, that America has "much to answer given its history in Latin America and the Middle East." Ultimately, Obama just seems to concede that America has a very flawed track record — a notion that was only confirmed when Michelle Obama's noted that "for the first time in my adult life I am proud of my country because it feels like hope is finally making a comeback."

Leaders have to earn the right to criticize their own team. If you're a winning quarterback who has sacrificed tremendously and succeeded — if nobody can doubt that you believe your team and your teammates are the best — then you have earned the right to call your guys out. It's why Kobe Bryant and Tom Brady can get away with yelling at their teammates while DeMarcus Cousins can't.

Obama has been more frank than any president in modern history in admitting to America's mistakes. His fans love this about him — he's a clear-eyed pragmatist who isn't afraid to apply rigor to analyzing the faults of himself and his countrymen, the president's supporters say. Maybe. But as a result, in the eyes of millions of conservatives, Obama has hardly built up a reservoir of trust that would grant him the moral authority to deliver Americans and Christians a scolding message about injustices in their collective pasts. My liberal friends might disagree — and claim that Obama's introspection and candor make him the perfect messenger for self-reflective realism — but the many Americans and Christians who find themselves on the wrong side of these criticisms would surely not give the president the benefit of the doubt. Fair or not, a Republican with a flag lapel pin is probably better positioned to challenge Americans and have this moment of reflection. The saying "only Nixon can go to China" is an apt one. Nixon's anti-Communism bonafides were beyond reproach — nobody would expect him to go soft on the red menace — a fact that gave him the space to do the unexpected and to reach out to China. It may not be fair, but it's much harder for a Democrat to pull of this kind of maneuver, and this is likely especially true of Obama.

Introspection and intellectual moral equivalence might work well in academia, or the world of political commentary. But it's not the kind of thing a leader — who truly believes he is leading a nation to summon the courage required to overcome a serious and immediate threat — usually voices. Our nation needs to be united and motivated far more than it needs to be challenged to engage in this this sort of intellectual navel gazing.

Facing the existential threat of godless Communism, Reagan didn't dwell on what was wrong with America. Churchill, in summoning the British people during the existential threat of World War II, didn't dwell on their faults — in fact, he talked about defending "Christendom" and western civilization. As Joe Scarborough told me on Morning Joe today, Obama's comments are "the equivalent of FDR, when giving a speech against Nazi Germany, going, 'Now, of course, what we did to the Indians...really bad....so we really have no room to talk about what Hitler is doing."

Obama doesn't see the world in black and white, good and evil. He's an academic and an attorney, someone who has always seen a grayer, more nuanced, world. That was a big part of his appeal in 2008. And one of the big lessons of his presidency may turn out to be that this actually isn't what we want in a leader.