Donald Trump has now named his son-in-law Jared Kushner as a senior adviser, notably on Middle East/Israel issues, and as Kushner fired me ten years ago over these issues, it seemed a good time to review my memories of our (limited) interactions and do what journalists do, make a prognosis about his future efforts.

Kushner was 25 when he bought the New York Observer from investment banker/artist Arthur Carter in 2006, and as all such transactions do, the move set off panic on the editorial side of the paper. The editor, my dear friend Peter Kaplan, now deceased, was at once engaged in a struggle with his new boss over the paper’s news budget and independence. For my part I had been a columnist for a few years, protected against attacks and my own ineptitude by my Harvard chum Kaplan (yes, Virginia, that’s how media works), and had lately started Mondoweiss there as a personal blog, and because I was vehemently against the Iraq war and beginning to connect that tragedy to the US relationship to Israel in my postings, I was apprehensive about Kushner’s view of the blog and me. I knew that he had been a big supporter of the orthodox Jewish Chabad House at Harvard and had lauded Alan Dershowitz there. Not a good sign — when I was discovering Rachel Corrie and The Israel Lobby.

Peter Kaplan was a great student of character; it was his chief delight in life (after a cigar, a turkey leg, and a Preston Sturges film in the middle of the night); and my understanding of Kushner’s character was formed by closed-door conversations with Peter. He told me that Kushner was smart, ambitious, and full of hubris. The two statements Peter made that resonate down through the years are: “Jared has ice in his veins.” And: “He doesn’t know what he doesn’t know.”

For a little while the clear-skinned young owner took Kaplan on as his grizzled guide to the world of journalism, but that interval was short-lived. It was somewhat shocking to Kaplan that a guy who had no experience of journalism, and was a boob about literature, wasn’t a very good reader, had spent his college years doing real estate deals, etc., was eager to make decisions about the paper’s values. But such is the way of the world, and after an agonizing couple of years Peter went back to Conde Nast.

I didn’t last as long. Jared and I had a few polite conversations in the year that we cohabited on Broadway, and two very uncomfortable meetings over Israel and Palestine. One was before I went out there in July 2006 on his dime to see the country for the first time, during the Lebanon War, and the second one was after I got back that August. In the first, Kushner told me about his Holocaust background, his grandparents who barely survived, and his regard for Israel. When I got back, Kushner and Brian Kempner, the newspaper’s publisher who had worked at the Israel lobby group AIPAC (American Israel Public Affairs Committee), couldn’t wait to hear what I had seen out there, they said. But when I started talking about the occupation, the room went cold as the poles, and Kushner gazed right through me with those unsmiling dark little eyes. Kaplan was even more uncomfortable than I was, and thankfully brought the tortuous meeting to a close.

But I managed to get a frank description of apartheid in Hebron into the pages of the Observer.

This couldn’t last. In February 2007 Kaplan closed his office door and said he was a Zionist, Kushner was a Zionist, Kempner was a Zionist, and the janitor was a Zionist, too, and the newspaper would not pay for me to blog, as I was demanding (at that time I was only paid for published columns). It was fitting; I was gone.

My interactions with Jared were limited, but they don’t give me hope about his ability to achieve peace in the Middle East. He lived in a deeply-Zionist-patriarchal mental space then; I never saw him take a step out of it. There was a provincial element to his commitment. As Peter said, he didn’t know what he didn’t know. The guy who replaced Kaplan was even more of a Zionist than Kaplan, while the nimble-footed Kempner went on to work in the Kushner real estate firm. Kushner’s ambition and political shrewdness were evident to us, but I never saw any worldliness or largeness of spirit. He was very impressed by his own family. The big asterisk is that he was 25 and 26. I wouldn’t want anyone to judge me on the basis of stuff I said at that age . . .

Lastly, I bear no ill will to Jared Kushner. He paid for my first trip to Israel and Palestine (at 50!); he paid for me to see the occupation. My firing was also a blessing; he cut me loose from the paternalist mainstream media, and I was forced to sink or swim on the internet. To some smaller or bigger degree, I can thank Jared for this website, and the wonderful relationships I have formed through the internet with people of strong hearts and principle, qualities prestige media culture does not select for. For the sake of all of us, I can only hope Kushner gets to enter a larger world too.