Anytime a commander in chief faces that question, it's a sure sign that something is wrong.

But Donald Trump and his administration are finding their humanity under scrutiny in the harrowing saga of kids separated from their parents after illegally crossing the southern border.

The administration's handling of the crisis lacked many things: coherence, competence and a duty to the truth over a crisis the President caused and blamed on others.

But there was something even more fundamental missing: compassion.

Trump furthered that on Friday, claiming that Democrats were making up "stories of sadness and grief" for political advantage.

"We cannot allow our Country to be overrun by illegal immigrants as the Democrats tell their phony stories of sadness and grief, hoping it will help them in the elections," he tweeted.

We must maintain a Strong Southern Border. We cannot allow our Country to be overrun by illegal immigrants as the Democrats tell their phony stories of sadness and grief, hoping it will help them in the elections. Obama and others had the same pictures, and did nothing about it! — Donald J. Trump (@realDonaldTrump) June 22, 2018

In essence, this human drama, lifted out of its Washington frame of warring politicians and dueling spin, is about kids who don't know where their parents are, adrift in a strange land.

"The children arrive, quickly asking, where is Mama, Papa? When can I see them again?" Donna Abbott, director of Bethany Christian Services Refugee and Immigrant Program told HLN's S.E. Cupp on Thursday, explaining the trauma of family separations.

But from the start, no one in the administration has shown that they really appreciate the emotional dimension of a story that has gripped the nation for days.

When Homeland Security Secretary Kirstjen Nielsen was briefing reporters Monday, for instance, her policy answers did not seem to match the emotion of the moment.

In one of the more extraordinary moments of any recent presidency, first lady Melania Trump left for a visit to the border Thursday wearing a jacket with a graffiti-style message on the back that read, "I REALLY DON'T CARE. DO U?"

In the ensuing media storm, her office insisted she was not making a political statement -- as speculation flew she was jabbing her husband's policies. The President later claimed she was taking a shot at the "fake news" media.

Yet the reason the slogan caused such a stir was the possibility that it was supposed to encapsulate the ethos of the administration.

And the administration's determination to make the moment a new front in its war with the media came across as another clumsy distraction from the human tragedies unfolding before the nation's eyes.

History's verdict

It's still unclear whether the last few days will hurt the President in the long term. It could possibly test Trump's view that he is bulletproof among his loyal base of supporters or prove to be a weak seam in his signature hardline immigration policy. And the separations issue is not the first time a President who prides himself on a strongman's image has seemed to lack compassion. His trips to hurricane disaster zones last year were jarring at times. And his constant jabs at Sen. John McCain, an Arizona Republican who is battling brain cancer, strike many in Washington as callous.

None of that seriously eroded his political position.

Yet it seems certain that the imagery and the feelings stirred will linger long after this political fight has been replaced in the mad whirl of Trump era headlines -- more than other rumbles of his presidency.

For much of his political career so far, Trump's lack of obvious compassion and tough rhetoric has been a selling point. It's been attractive to voters who believe the border has not been properly enforced and think that elite Washington politicians have been too meek to keep them and their culture safe. The most interesting intangible about the separations controversy is whether the emotive element of bereft children changes that equation. By reversing his policy, Trump may be revealing that he is not sure what the answer will be.

When they are over, presidencies are often defined in the public mind by snapshots in time: Ronald Reagan at the Berlin Wall, George W. Bush on a pile of rubble after 9/11 and John Kennedy asking Americans to ask themselves what they could do for their country.

The danger for Trump is that the last few days will form one of his snapshots. It may prove impossible to shield the President's legacy from pictures of kids in cages, crying toddlers and his own false assertions there was nothing he could do when he caused the uproar.

Pundits often overuse the analogy of Hurricane Katrina, when Bush peered down from Air Force One on the inundated Gulf Coast in 2005 as stranded Americans died on the streets of New Orleans, deserted by their government.

Back then, a president failed to understand the depth of feeling as a nation that sees itself as a beacon of compassion watched searing television pictures of human suffering.

While the events of the last week are of a smaller scale, it feels like another moment when swelling national feeling took a president off guard.

PR disaster

Belatedly, the White House has realized it has a public relations nightmare on its hands. Sources told CNN the President was convinced of the need to reverse his claim that he could not stop the family separations by heartrending audio and video of bereft children.

Then the first lady headed to the border to assess the situation for herself.

"I'd ... like to ask you how I can help to these children to reunite with their families as quickly as possible," she told medical staff at a children's shelter.

On Twitter, Ivanka Trump thanked her father for stopping the practice of separations his own administration had introduced and she called on Congress to find "a lasting solution that is consistent with our shared values."

Kristen Soltis Anderson, a Republican pollster, said Trump understood the importance of horrifying imagery.

"I would imagine that the White House would want Melania to go down there and provide some positive visuals ... to try to make it seem as though they care about the outcome and the welfare of these kids," Anderson told CNN's Jake Tapper.

Yet the visit did seem a little contrived, featuring a facility that looked like a brightly decorated schoolroom that was far more welcoming than cages holding some kids in groups or the ordeal of more than 200 other children who were bused to New York.

Ivanka Trump's tweet, meanwhile, seemed oddly detached -- as if she were just an outside observer rather than a member of the administration that enforced the "zero tolerance" policy that led to the separations.

Efforts to show compassion toward the children might also have come too late to change the narrative.

Attorney General Jeff Sessions protested on Thursday in an interview with the Christian Broadcasting Network that "the American people don't like the idea that we are separating families. We never really intended to do that."

Earlier, the President confessed at a Cabinet meeting that "it bothered me, as it bothered everybody at this table. We are all bothered by it."

But judging by its own statements, the administration used family separation as leverage to stop more migrants coming over the border and to try to jam Congress into fixing the issue -- in bills that would achieve many of Trump's immigration policy goals.

Earlier in June, White House chief of staff John Kelly said in an NPR interview that family separation was seen as a "tough deterrent" to illegal migration.

And Sessions said on May 9, the day the new policy was publicized: "If you don't want your child to be separated, then don't bring them across the border illegally."

There's not much the administration can do to correct those missteps now.

But a lack of compassion was also evident in its failure so far to tell Americans how it plans to reunite 2,300 children and their parents who were separated after crossing the border before Trump reversed the policy.

Trump has spent the last two years dehumanizing undocumented migrants, and using immigration as a base-cementing strategy.

The danger for him now is that the last few weeks may come to be seen as the moment when the human consequences of his approach became clear -- and rebounded against him.