Sidney Zion in his Upper West Side home in 2007.(Thrive NYC/Community Media LLC)

Sidney Zion, who had a love-hate relationship with The New York Times, might well have almost approved of his Times obit.

It was the lead obit, it appeared the day after he died, it featured a flattering photo, it ran to a respectable length, it accurately identified most of the highlights of his uniquely colorful and controversial career, and it didn’t mention his dropping the dime on Daniel Ellsberg, which caused the Times to blacklist him at the time, until three-quarters of the way down in the piece. Instead, the obit highlighted his lawsuit against the hospital he held responsible for his daughter Libby’s tragic death. It was fair.

But for me, it didn’t capture what made Sidney Sidney, which had to do with his unique take on both his journalism and his Jewishness. Since I was there, so to speak, at the creation, herewith my Sidney Zion, aka El Sid.

I first met El Sid in the fall of 1956, when we were fellow students at Yale Law School. I was attempting to launch Monocle, which we called “a leisurely quarterly of political satire.” (That meant it would only come out twice a year.) A classmate said that if I was starting a satire magazine, I had to meet Sidney. When I asked why, he said meet him and you’ll see why.

I met, I saw, and he conquered. In the obit, the Times called Sidney Runyonesque, and indeed the cigar-smoking, scotch-sipping, Hit-Parade-humming Sidney’s first story for Monocle—about the integration of a grade school in Arkansas, over the opposition of its governor, Orville Faubus—was called “The Day They Put the Snatch on Orville.” It included a cast of characters right out of Runyon, and it was written in Runyon’s trademark present-tense Broadwayese.

We immediately hit it off, and not just because we, as would-be journalists, were both fans of Yale’s odd-man-out law professor, Fred Rodell, who taught his seminars at Mory’s, a local bar, so that he could partake of their libations. What really impressed Sidney was his discovery that in 1946, when I was in the eighth grade, I had worked as a “volunteer” (actually, we were paid $2 an hour) to pass a contribution basket at Ben Hecht’s play, A Flag is Born, which advocated for a Jewish homeland in Palestine. The money, although nobody said it out loud at the time, was going to support the Irgun Zvai Leumi, Menachem Begin’s militant underground movement.

Hecht, it turned out, was Sidney’s hero. Not just because he was a journalist’s journalist, playwright, screenwriter, and man about town, but because, as the author of A Guide For The Bedevilled—Sidney’s bible—he was a Jew’s Jew. Sidney, who kept track of these things, reminded me that after A Flag is Born closed, Hecht had used his own proceeds from the play to take out an ad in The New York Herald Tribune congratulating the Irgun on blowing up British trains, robbing British banks, killing British Tommies.

Not that we were in political sync across the board. We both saw ourselves as First Amendment absolutists in the Black-Douglas tradition, and we both had a healthy contempt for what we thought of as Harvard-inspired Frankfurterian judicial self-restraint. But Sid, it turned out, had been chairman of the Eisenhower for President Club while a student at the University of Pennsylvania, whereas I, in the argot of the day, had been “Madly for Adlai.” When I asked Sid how he could have supported the Republican, he passionately explained that Roosevelt, whom he considered an anti-Semite, “didn’t lift a finger” to save the Jews of Europe. As Ben Hecht had once put it, FDR was “the humanitarian who snubbed a massacre.”

Monocle, it turned out, was a short-lived magazine. It graduated from Yale Law along with the rest of us, and after a number of years as what we called “a radical sporadical,” it expired in 1965. But it had a long-run impact on Sid’s life.

He met his wife-to-be, Elsa Heister, at a Monocle party. And in 1962, when the New York newspapers went on strike, Monocle put out a parody of the New York Post, called The Pest, to which Sid contributed a column in the cryptic style of the paper’s incomparable columnist, Murray Kempton.

Nora Ephron, herself a contributor to The Pest, tells what happened next: “The story was that the editors of the Post were in a rage. [They] wanted to sue. And Dolly [Schiff, the newspaper’s legendary owner] said, ‘Don’t be idiots. If they can parody us they can write for us. Hire them.’” And that’s what happened. After the Post, Sid went on to report on and cogitate about the law for The New York Times, to columnize for the Daily News, and to write for periodicals too numerous to mention.

I’ve already said that Sid had a love-hate relationship with the Times. Let me give an example. In his last years at the Times, Sid got a tip that Judge Henry Friendly, then perhaps the preeminent appellate court judge in the country and prominently mentioned as a possible U.S. Supreme Court nominee, many years earlier failed to disqualify himself from ruling on a case in which he had a conflict of interest. Assured by Managing Editor Abe Rosenthal that if he got the goods the Times would print the piece, Sidney spent the next weeks definitively documenting the story. But when the time came to print it, Rosenthal was overruled by James Reston, who was then running the paper. Reston summoned Zion into his 10th floor office, and from behind his imposing desk, explained that if Friendly actually received a Supreme Court nomination, the Times would run the story. But absent that, Reston was not about to run a piece that would cast a dark shadow on Friendly’s otherwise distinguished career.

“The difference between you and me, Mr. Zion,” Reston said, “is that you were brought up as a poor Jew on the scrappy streets of Passaic, New Jersey, whereas I was brought up in the Church of Scotland outside of Glasgow.” At this point, Sidney rudely interrupted. “I thought that the difference between us,” he said, “is you are sitting there, whereas I am sitting here.”

In 1971, after he quit the Times to co-found Scanlan’s Monthly with Warren Hinckle, Sidney made worldwide news and incurred what seemed at the time the everlasting enmity of his erstwhile Times colleagues because he named Daniel Ellsberg as the leaker of the Pentagon Papers. He was roundly denounced as a snitch, an informer. How could he do such a thing?

For better or worse, here’s how. From Sid’s perspective, the Times was campaigning for a Pulitzer Prize that it didn’t deserve. The man who took the real risks was the man whom the Times said the world would never know. Oh yeah?, said macho Sid, who vowed to prove his prowess as an investigative reporter and bragged that he could find out who it was in a matter of days, and did just that. After he announced his find on the radio, the world descended on Sid The Informer.

This all struck me as ironic, because Sid himself had long detested those who played the informer. In fact, one of the first pieces Scanlan’s ran was titled “Hello, Informer,” a reprint of Elia Kazan’s testimony before the House Un-American Activities Committee. Scanlan’s sent him a check for $150, which he never cashed.

A few weeks before Sidney died, my friend Christopher Lehmann-Haupt and I had dinner with him at Frankie and Johnnie’s, one of his favorite haunts, and wouldn’t you know it, we had a long and loud argument about Israel. It was two against one—or three against one, since the woman at the next table vociferously took objection to my point that not all those who objected to the settlements or Israel’s failure to honor Palestinian human and civil rights and liberties were “anti-Israel.” There were cries and gnashing of teeth, but had there not been, it wouldn’t have been Sid. And now the world is poorer without his furor.

Although he fasted on Yom Kippur and went to shul on the High Holidays, I never realized that Sidney, who fraternized with more than his share of mobsters, who spent too many evenings commuting between the bars at Gallagher’s, Frankie and Johnnie’s, and Elaine’s, was particularly religious. So I was surprised to learn at his funeral that his daily ritual included the laying of teffilin. According to the rabbi, “totafot,” the word the Torah uses to describe the teffilin, is either untranslatable or means “immovable.” Now that I think about it, I am no longer surprised. El Sid was definitely untranslatable, and he was certainly immovable.

Victor Navasky, a political columnist for Tablet Magazine, is a professor at Columbia’s Graduate School of Journalism and the chairman of the Columbia Journalism Review.