White House Press Secretary Sean Spicer was in damage control Tuesday night, hours after he compared Adolf Hitler’s murderous Nazi tactics of the Holocaust to those of the deadly chemical attack launched in Syria last week by its President Bashar al-Assad. The controversy forced Spicer to issue apologies across the board, including a major supporter of President Donald Trump who just happens to be one of the nation’s most prominent Jews, Sheldon Adelson.

“We didn’t use chemical weapons in World War II,” Spicer told reporters during the daily press briefing at the White House on Tuesday. “You know, you had someone as despicable as Hitler who didn’t even sink to using chemical weapons.”

Read: Sean Spicer's Hitler Comment Mocked With Memes And Gifs On Internet

Spicer, who ultimately admitted that Hitler did indeed use deadly chemicals to gas Jews being held in Nazi concentration camps, went on to say that Hitler “was not using the gas on his own people the same way that Assad is doing.”

The new White House press secretary is no stranger to controversy, as he has been the subject of scrutiny since he assumed his current position beginning in January. But his latest apparent flub may have set off the biggest firestorm yet in his fewer than three months on the job.

Below is a timeline of other instances where Spicer sparked somewhat of a controversy over his words during a press briefing.

Jan. 21: The day after Trump was inaugurated, Spicer declared it “was the largest audience to ever witness an inauguration – period.” Days later, he would call his remarks an honest mistake.

Feb. 6: Spicer adamantly denied Trump owned a bathrobe one day after the New York Times published a story that included a reference to the new president “watching television in his bathrobe.” Trump “definitely doesn’t wear one,” Spicer said during his press briefing that day. Photo evidence to the contrary would surface on social media hours later.

May 10: Spicer presided over the daily press briefing that day in his typical get-up of a business suit and pocket square, but there was one apparent anomaly that escaped the press secretary’s eye: His American flag pin. Reporters took the fashion faux pas as a “sign of distress,” as described by the U.S. code on respect for the flag.

March 28: After months of ridicule and scrutiny, Spicer appeared to put his foot down when a reporter asked him about Russian ties to Trump and his administration. “I've said it from the day that I got here until whenever that there's not a connection. ... If the president puts Russian salad dressing on his salad tonight, somehow that's a Russian connection,” Spicer told reporter April Ryan. “I'm sorry that that disgusts you. You're shaking your head."

That exchange was dripping with highly charged sexist language, former Secretary of State Hillary Clinton said later that day.

“April Ryan, a respected journalist with unrivaled integrity, was doing her job just this afternoon in the White House press room when she was patronized and cut off trying to ask a question,” Clinton told attendees while delivering the keynote address at the Professional BusinessWomen of California conference in San Francisco.