Sean Spicer resigned Friday after his stormy nine-month tenure as White House press secretary. Spicer’s Herculean task of being the administration’s media point-person led to controversy from the first night of Trump’s presidency until his resignation. From berating the media over the attendance size of Donald Trump’s inauguration to sparring with journalists over the lack of on-camera briefings, Spicer’s 181-day tenure has been filled with bloopers and gaffes – some more funny than others. Many of these moments directly concerned Israel and the Jewish world.

Several days before Trump’s inauguration, the press secretary-designate came out swinging on Israel, telling journalists that Trump's promised move of the U.S. Embassy in Israel from Tel Aviv to Jerusalem is “coming soon” and encouraged journalists to “stay tuned.” Days later at his first official briefing, Spicer attempted to walk back his cryptic comments, stating that no official decision had been made and that the White House was at the “very early stages” of the decision-making process.

Spicer also managed to successfully duck questions about Israel’s decision to build 2,500 new housing units in West Bank settlements, a move likely emboldened by Trump’s campaign rhetoric. Spicer only managed to say that the move would be discussed during Netanyahu’s planned visit. Spicer also managed to implicitly criticize Barack Obama’s last-minute transfer of $220 million to the Palestinian Authority, saying that Trump is “very concerned on how American taxpayer money is being spent,” adding that the administration will be "examining all aspects of that," to make sure that money being spent by the U.S. government abroad serves American interests. The aid money was later released in full without much fanfare.

As Spicer was beginning to create a pattern of evasion concerning Trump policy on the Israeli-Palestinian conflict, the White House released a statement marking International Holocaust Remembrance Day that failed to mention Jews. Despite near-universal criticism of the omission, Spicer called complaints “pathetic” and “disappointing,” adding that “by and large he’s been praised for it,” adding that the statement was written “with the help of an individual who is both Jewish and the descendant of Holocaust survivors.”

Over the next several weeks, a spate of bomb threats targeting Jewish centers throughout North America and cemetery vandalisms rocked the U.S. Jewish community. In his official statement of condemnation, Spicer avoided the words “Jewish” or “anti-Semitic”, simply stating that “hatred and hate-motivated violence of any kind have no place in a country founded on the promise of individual freedom” and “the president has made it abundantly clear that these actions are unacceptable” as Trump snapped at an ultra-Orthodox Jewish reporter who asked him how he planned on tackling anti-Semitism.

Several days later, Spicer managed to include anti-Semitism in his condemnation, saying “The president continues to condemn these and any other form of anti-Semitic and hateful acts in the strongest terms. No one in America should feel afraid to follow the religion of their choosing freely and openly.”

After managing to avoid any major scandals specifically related to Israel or the Jewish world in March, Spicer’s greatest gaffe (potentially of his entire tenure) came following Syrian President Bashar Assad’s chemical attack and Russia’s subsequent cover-up.

"We had someone as despicable as Hitler who didn't even sink to using chemical weapons," Spicer said. "So you have to, if you're Russia, ask yourself is this a country that you want to align yourself with?"

Spicer immediately tried to clarify his remark. Hitler "was not using the gas on his own people the same way Assad is doing," Spicer said, adding that the Nazis only used chemical weapons in "Holocaust centers," evidently referring to death camps.

Calls for Spicer’s resignation or firing were immediate, from Israeli cabinet ministers to U.S. Congressmen, NGOs and Holocaust memorials. Even Yad Vashem called on Spicer to check out their website. Spicer apologized publicly during an interview with CNN’s Wolf Blizter, saying that "frankly, I mistakenly made an inappropriate and insensitive reference to the Holocaust, for which there is no comparison," Spicer said. "And for that I apologize. It was a mistake to do that."

He also personally apologized to Sheldon Adelson, a move many felt inappropriately cast the Republican mega donor as official representative of the Jewish people.

Several weeks after following Spicer’s Holocaust center remarks, Trump shared top-secret Israeli intelligence with Russian officials during a meeting at the White House, the New York Times originally reported. When asked about the report, Spicer curiously referred reporters to Israeli Ambassador to the U.S. Ron Dermer’s statement that "Israel has full confidence in our intelligence-sharing relationship with the United States and looks forward to deepening that relationship in the years ahead under President Trump."

Since that incident, Spicer has kept a low public profile, dogged by constant rumors of his impending dismissal and an increasingly press-averse White House that has made most of its press briefings off-limits to cameras. Spicey, we hardly knew ye.