There’s no good time to make a Hitler comparison, but deploying one in the midst of Passover to justify voluntary airstrikes is an especially unwise choice, as White House Press Secretary Sean Spicer realized, to his chagrin, Tuesday afternoon.

Spicer was fielding questions about the Trump administration’s confusing and diffuse strategy toward Syria when he was asked why the White House believed that Russian President Vladimir Putin would break with Syrian President Bashar al-Assad at this moment.

“You look, we didn’t use chemical weapons in World War II. You had someone as despicable as Hitler who didn’t even sink to using chemical weapons,” Spicer said.

As puzzled reporters and other observers immediately noted, Spicer’s statement was deeply confusing, even if one could make a case it was accurate in very narrow terms. The Nazi government did not release chemical weapons on the battlefield during World War II. This may be the point Spicer was trying to make, as Defense Secretary James Mattis used a similar line later Tuesday afternoon.

But as Amarnath Amarasingam wrote here last week, the toxic agent that Assad used last week in Idlib, sarin gas, was discovered and then weaponized in Nazi Germany. Hitler decided not to use chemical weapons in combat, apparently in part because of fears that any Nazi use of chemical weapons would elicit much more destructive Allied use in retaliation.) Hitler nonetheless oversaw the most lethal use of chemical weapons in history. Nazis killed perhaps 1 million people, most of them Jews, using the poison gas Zyklon B.

(The Allied history with chemical weapons is not spotless. Winston Churchill considered, but rejected, a plan to use mustard gas a defensive measure in the event of a Nazi invasion. In 1943, a German air raid in Italy caused the release of mustard gas that was being transported on Allied ships, also for potential combat use. The incident was hushed up.)

A few minutes later in the briefing, Spicer had a chance to clean up his statement.

“I think when you come to sarin gas, [Hitler] was not using the gas on his own people the same way Assad was,” Spicer started out, heading down another rocky road. Some of the Jews who were killed would have been Germans who had been stripped of citizenship, although it’s unclear why the use against one’s own citizens is more despicable.

Seeming to realize his error, Spicer added, “[Hitler] brought them into the Holocaust centers, I understand that. But I was saying in the way that Assad used them, where he dropped them down to innoc—into the middle of towns, it was brought—so the use of it, I appreciate the clarification, that was not the intent.”

That, too, was fraught. Aside from the strange use of “Holocaust centers,” Spicer’s abortive invocation of “innocence” was nonsensical as well. Following the briefing, Spicer issued a statement:

In no way was I trying to lessen the horrendous nature of the Holocaust, however, I was trying to draw a contrast of the tactic of using airplanes to drop chemical weapons on innocent people.

Yet again, Spicer’s choice of words makes little sense: Were Holocaust victims any less innocent for having been rounded up and interned before they were killed? Indeed, Spicer than issued another statement changing the final phrase to “using airplanes to drop chemical weapons on population centers.”

Spicer is not the first to make an ill-advised comparison between Assad and Hitler. The author and television writer David Simon, of The Wire fame, made a similar argument on Twitter last week:

The problem here, as with all Hitler analogies, is that comparing anyone to history’s greatest villain feels as though it is a trump card when in fact it tends to undermine whatever argument it seeks to bolster. On the one hand, almost any comparison between the barbarity of a modern figure and Hitler will quickly fall apart. On the other, it always demands a single course of action, all-out war against the target, which paralyzes any debate.

The point here is not that Spicer is a Holocaust denier; his debacle today looked like the product of a series of errors, rather than ideology. The point is that he, and the Trump administration more broadly, are deeply sloppy in their messaging approach, and are as a result fall into grievous errors and then keep digging. And there is no greater danger for the improvising, combative speaker than foolishly invoking the Holocaust.

Indeed, the Trump administration has already done so once before. In January, a statement for Holocaust Remembrance Day inexplicably omitted any mention of the Jews. When called out, Spicer tried to suggest that was both intentional but also entirely reasonable. “The president went out of his way to recognize the Holocaust and the suffering that went through and the people that were affected by it and the loss of life,” Spicer stammered, as though this were some sort of extreme measure.

It’s clear that there’s little forethought about when to roll out Hitler comparisons. On Monday, Spicer refused to say whether the White House even considered Assad a war criminal. On Tuesday, Spicer said that in at least one respect, Assad was worse than Hitler. That is messaging whiplash, but it makes even less sense in practical terms. During the same briefing, Spicer said that while the Trump administration did not see a future for the Assad regime, its focus for the time being is on defeating ISIS.

But if Assad is worse than Hitler, how can the U.S. possibly defend anything short of immediate regime change? Hitler analogies are terrible political rhetoric, but they are even worse as the basis for policy.