IN THE SUMMER OF 2019, when Robert M. Morgenthau, who reigned over New York law enforcement for six decades, died, 10 days short of his 100th birthday, eulogies filled the newspapers, the governor ordered flags to half-staff, and the man in the White House weighed in. “I was saddened to learn of the recent passing of Bob Morgenthau, a truly great man!” Donald Trump wrote on Twitter.
Mr. Morgenthau, who had served as district attorney for 35 years and before that spent nearly a decade as the U.S. attorney in the Southern District of New York, was “a warrior for our Country that he loved so dearly,” Mr. Trump tweeted. He added minutes later, “Bob Morgenthau, a legend, will be greatly missed!”
Alvin Bragg, the Manhattan district attorney, may bring an indictment against Mr. Trump — the first time that a former U.S. president would be charged with criminal wrongdoing. Mr. Trump has said he will be arrested. Beneath Mr. Trump’s shrill defense lies four decades of history: a relationship with the former D.A., perplexing in retrospect, that spanned Mr. Trump’s rise from Queens to the White House. Mr. Trump’s relationship with Mr. Morgenthau afforded Mr. Trump access to power, a measure of respect and, at least from Mr. Trump’s perspective, an ally should the need arise.
Just last week, on Truth Social, the MAGA social media site, the former president heaped praise on “my friend, the late, GREAT, Robert Morgenthau.” But this time Mr. Trump went further: “the legendary & highly respected District Attorney of Manhattan, would be spinning in his grave if he were told that his Office was even thinking about bringing charges against the 45th President of the United States.”
It’s true Mr. Morgenthau knew Mr. Trump — “at close range,” Morgenthau would say — for nearly 40 years. It’s also true that since they met in the 1980s, Mr. Trump has done his utmost to declare his admiration for “the Boss,” the nickname used for Mr. Morgenthau. Mr. Morgenthau, for his part, never hid the relationship. Mr. Morgenthau long kept close the real estate clans that controlled acres of Manhattan. (Fred Wilpon, for years a principal owner of the Mets, was a friend since the 1960s; Peter Kalikow, another magnate and a onetime owner of The New York Post, was also a pal.) Mr. Morgenthau enjoyed wealthy acquaintances, but over the decades, few called the D.A.’s office and were called as often as Mr. Trump was.
I spent a decade, and hundreds of hours, interviewing Mr. Morgenthau for an unauthorized biography of the D.A. and four generations of his family. I interviewed more than 300 others, many who served in his office, many who opposed him in court or in politics. I learned that since his first days as U.S. attorney under John F. Kennedy, Mr. Morgenthau feared no defendant: He indicted a former dean of Harvard Law School (a beloved Kennedy crony) for tax fraud, as well as a chairman of the New York Stock Exchange. Louis Wolfson was one of the richest men in the United States in 1966, the year Mr. Morgenthau indicted him twice.
As D.A., Mr. Morgenthau went after mob bosses and corporate executives, the chief of the Saudi intelligence service and a generation of crooked cops. Most famously, he reversed course on the Central Park Jogger case, overseeing the 2002 reinvestigation that led to vacating the convictions of the five young men wrongfully accused of the attack and rape of Trisha Meili. There were also missteps, even miscarriages of justice. But when he retired in 2009, he had graduated generations of former assistants to the bench (the most notable: Sonia Sotomayor).
In the 1960s, as the chief federal prosecutor, he turned the Southern District into an inviolable fief, the “Sovereign District.” As D.A., he vowed to fight crime in the suites, as well as in the streets. And with the investigation of the Bank of Credit and Commerce International (and the serial indictments that followed), he expanded his county jurisdiction to the entire world. For almost half a century, his record revealed no favoritism: Mr. Morgenthau went after Democrats and Jews — and, often, Jewish Democrats. And yet, in hindsight, it’s not hard to see why Mr. Trump might think otherwise.
Mr. Morgenthau and Mr. Trump were friends in much the same way that politicians and fixtures on the city’s social circuit call one another friends. They did have a relationship, and it was transactional. They saw each other most often at award galas and benefit dinners. “I like Donald,” Mr. Morgenthau told me, adding that he “writes checks.” Mr. Trump, the D.A. explained, was a patron of the three causes dearest to him: the Police Athletic League, which organized summer and after-school play for 50,000 city kids at that time; the Museum of Jewish Heritage (a Living Memorial to the Holocaust, as it calls itself), which the D.A. helped found; and Mr. Morgenthau’s political career. Mr. Trump gave money to the D.A.’s two most contentious campaigns, in 1985 and 2005.
Two dates in May 1989 reveal how they could share a dais, even while standing on opposite sides of an issue. On May 1, in the wake of the attacks in Central Park, Mr. Trump published his now-infamous newspaper advertisements, decrying the “roving bands of wild criminals” and calling for the death penalty’s return. On May 17, the Police Athletic League held its annual benefit gala at the Plaza Hotel: Jackie Mason entertained the crowd, Don Johnson and a pregnant Melanie Griffith posed for the cameras, and Mr. Morgenthau presided. That evening, those assembled honored the year’s “Superstar,” who also happened to be their host, the new owner of the hotel: Mr. Trump.
The P.A.L. was the golden door. In the 1980s, Mr. Morgenthau invited Mr. Trump onto the board. The P.A.L. gave the young developer, from Jamaica Estates in Queens, what he lacked and what he wanted most: entrée to New York officialdom. Suddenly Mr. Trump was in a tuxedo mixing with the city’s wealthiest executives and top brass of its police department — with photographs appearing in the newspapers the next day. Communiqués from Trump Tower became routine: Across a news clip recounting the D.A.’s latest exploits, Mr. Trump scrawled in black Sharpie a pat on the shoulder: “Bob — You are the GREATEST!” — followed by his seismographic signature.
The next year, Mr. Morgenthau again helped Mr. Trump build a bridge into Manhattan, brokering a civic achievement: the renovation of the Wollman Rink in Central Park. For years the rink had been a symbol of municipal ineptitude — a sinkhole that swallowed millions of city dollars. Mayor Ed Koch faced a political disaster and asked Mr. Morgenthau a favor: Would he approach Mr. Trump? “Ed feared Donald, or at least getting too close to Donald,” the D.A. told me. Mr. Trump took on not only the main rink but also its little sister, the Lasker Rink near East Harlem, which was used by the P.A.L. Mr. Trump vowed to do the job in six months for $3 million. He did it in less time and for less money. He also made certain that each step, from the pipe laying to the cement pouring, was lavishly documented for the press. Only later did the D.A. recognize the significance. “That rink put him on the map,” said Wayne Barrett, an investigative journalist and the author, in 1992, of the first biography of Mr. Trump. “It was the turning point.”
***
BEFORE Mr. TRUMP’S 2016 run for the White House, whenever I asked Mr. Morgenthau about Mr. Trump, he was willing to tolerate Mr. Trump’s coarse, often reckless, views. He even overlooked Mr. Trump’s lawyer Roy Cohn, a man Mr. Morgenthau indicted three times and each time failed to convict. The D.A. and the developer were unlikely allies. “Donald idolized Bob,” Lucinda Franks, Mr. Morgenthau’s second wife, who died in 2021, said. “To him, Bob was the ultimate New Yorker. He was the establishment, everything he was not.” In the late 1990s, Mr. Trump took to attending the D.A.’s swearing-in ceremonies, even inviting Mr. Morgenthau and his family — his wife and their two children — to Mar-a-Lago. (They flew down during a spring break from school, staying in a cottage on the grounds.)
All the while, the contributions continued: Mr. Trump gave to the P.A.L. and to the D.A. himself. In his 1985 re-election race, as Mr. Morgenthau faced an early challenge from the civil rights lawyer C. Vernon Mason, Mr. Trump gave $5,000 — the campaign’s second-largest contribution. In 2005, Mr. Trump hosted a fund-raiser for the D.A. at Trump Tower. In part, Mr. Trump agreed to host the event because a rumor had reached the D.A. that Mr. Trump’s sons were raising funds for Leslie Crocker Snyder, Mr. Morgenthau’s challenger.
The prosecutors who led Mr. Morgenthau’s investigations division across the decades were, as of late, emphatic in their defense, explaining why the office never began a full-scale investigation of Mr. Trump’s business: “Why didn’t Morgenthau do anything? Because there was nothing to do,” said Michael Cherkasky, his investigations chief for six years. The assistants, like their former boss, blamed the political process. “You have to raise money to run for D.A.,” said Mr. Cherkasky. “You ask people for money, and you can’t do anything in return for it. There’s no favors. There’s no nothing.”
The P.A.L. was the beginning, but Mr. Trump gave his biggest check to the other charity Mr. Morgenthau chaired. In 2012, Mr. Trump gave $100,000 to the Museum of Jewish Heritage, only after the D.A. complained that Mr. Trump’s son-in-law Jared Kushner, a new museum board member and the scion of Kushner Companies, the family real estate company, had failed to make good on a promised donation. Mr. Morgenthau knew Mr. Kushner: He interned in the D.A.’s office in 2004, the summer his father was arrested on federal charges. “Nasty piece of work,” the D.A. said of the younger Kushner: “I had to kick him off the board.”
***
LAST MONTH I returned to the D.A.’s office to speak about Mr. Morgenthau’s tenure and legacy. I told the prosecutors in the audience — including those leading the investigation of the 45th president — that from all I’d learned about the D.A. and his relations with Mr. Trump, there was no mystery and no smoking gun. Their relationship made perfect sense.
Each saw opportunity in the other: The D.A., ever expedient in his drive to fund his favored causes, needed the checks, and the real estate man, ever eager to antagonize a business foe, sought an ally in law enforcement. The D.A. would not serve as a shield but more as a decoy for Mr. Trump, who could use his proximity to Mr. Morgenthau’s power to enhance his own reputation. The D.A. had a blind spot when it came to Mr. Trump, one he would recognize years later. In his final years, Mr. Morgenthau witnessed a new blood lust — demonization of immigrants and people of color, the rise of white supremacy — and was taken aback. One morning in the spring before his death, I asked Mr. Morgenthau what his greatest fear was, and he did not hesitate to answer: “Trump.”
In more than a decade of digging, I never found a case in which Mr. Morgenthau took a dive or closed an eye. Could he have found criminal wrongdoing in the Trump Organization? Cyrus Vance, the Manhattan D.A. from 2010 to 2022, spent more than three years and untold millions — some of it taxpayers’ money — trying and came up short.
I remember what Mr. Vance told me weeks before he left office. “I feel Bob’s spirit here every day,” he said. A biographer cannot prognosticate; the past is evasive enough. Should Mr. Bragg indict the former president, the spirit of the office’s longest occupant will not howl with fury. Yes, Mr. Morgenthau once introduced Mr. Trump, in another call to the dais, as a “great New Yorker who has made this a great city,” but I’ll bet Mr. Morgenthau will rest just fine, knowing that what he cared most about, the integrity of the office, is alive and well.
Andrew Meier is the author of “Morgenthau: Power, Privilege, and the Rise of an American Dynasty,” from which this essay is adapted.
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