Success Academy’s board chairman and major charter school donor Daniel Loeb made headlines this month for posting a racially charged comment on Facebook that compared an African-American New York state senator with the Ku Klux Klan.

Loeb deleted the post, apologized, and left Success Academy and other charter school organizations scrambling to condemn his behavior — and explaining why he would remain on their boards.

Loeb represents a double-edged sword for charter schools. He is a wealthy and well-connected hedge fund manager, who has given millions of dollars to the charter school cause. But his actions force Success Academy CEO Eva Moskowitz and other charter leaders to make a calculation: Is his behavior a fair price to pay for the boost to their cause?

So far, they have apparently decided that it is. He has not yet been removed from Success’s board. Here are other things Eva Moskowitz has had to grapple with — which include a string of insensitive comments, but also his support for other progressive causes— as she has navigated her relationship with Loeb over the years:

He’s a nonpartisan ally — and antagonist. Loeb supports both Democrats and Republicans, and he also attacks candidates and lawmakers on both sides of the aisle. For example, he’s a major backer of New York Gov. Andrew Cuomo, but he has given to Republican mayoral candidate Nicole Malliotakis and supported Mitt Romney in past presidential campaigns. At the same time, he has lashed out at both Hillary Clinton and Barack Obama, often in withering and offensive terms, while also telling friends he would not vote for Donald Trump.

This isn’t the first offensive comment he’s made. Far from it, in fact. Loeb is fast-fingered on Facebook and frequently uses derogatory language to lash out at people who have made him unhappy. Here are a few of the examples that have been reported previously:

  • Another time Loeb compared the unions and their supporters to the KKK: Loeb posted the following on his Facebook page in 2016, first reported by Dealbreaker: “If you truly believe that education is the dividing line (and I concurr) then you must recognizer and take up the fight against the teachers union, the biggest single force standing in the way of quality education and an organization that has done more to perpetuate poverty and discrimination against people of color than the KKK.”
  • Using a derogatory term for people of color: Loeb once got into a fight with Fairfax Financial, a Canadian insurance company, which resulted in a lawsuit. Reported Reuters in 2011: “Fairfax’s filing quotes Loeb as saying he found the situation somewhat ironic because “the odds are much greater of being strung up by a Canadian Jew than a Canadian schwarze.” Loeb, who is Jewish, used “schwarze,” a derogatory Yiddish word for a black person, to describe Watsa, who is of Indian ancestry.”
  • Making light of domestic violence by comparing Obama to an abuser: In a 2010 letter to hedge fund managers who had supported Obama, Loeb wrote, according to CNBC: “I am sure, if we are really nice and stay quiet, everything will be alright and the President will become more centrist and that all his tough talk is just words; I mean he really loves us and when he beats us, he doesn’t mean it; he just gets a little angry.”
  • Making a xenophobic, homophobic attack against a rival: A damning 2013 Vanity Fair profile dredged up an anecdote from 1999, when Loeb was feuding with John Liviakis, a San Francisco public-relations executive. In an “imaginary monologue” in the voice of Liviakis, Loeb wrote under a pseudonym: “Then I will laugh at you fools for buying my shares and I will celebrate with a bottle of grappa, some fresh feta, and a nice young boy-just like in the old country.” Liviakis sued him for libel.

Loeb’s allies say his mean-spirited comments don’t necessarily reflect deep-seated beliefs. “I have known Dan to be a champion for underserved children who has worked tirelessly for years on their behalf,” said Jenny Sedlis, the head of StudentsFirstNY and a former deputy to Moskowitz, last week. “I know from first-hand experience the post he made does not reflect his true beliefs or the person he is.”

He has championed progressive causes in the past. Most notably, Loeb helped get gay marriage on the books in New York by throwing his influence into winning over Senate Republicans. This position put him in line with most Democrats and with Moskowitz, who has had wide support in New York City’s gay community for nearly 20 years. It also suggests that some of his internet posts, which have included seemingly homophobic comments, do not necessarily reflect the entirety of his beliefs.

It’s also not his first ethical challenge. Loeb had an account on the marital cheating site Ashley Madison, though he later said he did not use the site to engage or meet anyone on the site. He also has garnered criticism for the way he uses online message boards, where some business insiders say he plays fast and loose with federal regulations about the ways hedge fund operators can communicate with investors. And multiple accounts have him hitting a Cuban child with his car during a vacation in 2002, although he and his friends tell different versions of that story.

His friends and investors have their own problems. At Third Point Management, Loeb manages $17 billion and has a host of high-profile investors — including someone else who landed in hot water for speaking freely this summer. Anthony Scaramucci told Vanity Fair that Loeb was “one of the best investors of his generation. . . . He is the guy that would chew through the wallboard to create a return for his investors.” At the time, Scaramucci had invested about 10 percent of his own fund’s $500 million with Loeb. Now, of course, he’s better known as the man who served for 10 days as Trump’s White House communications director before resigning after making a profanity-laden public attack on other White House officials.