The Drake Hotel was a Roaring 20s–era New York mainstay, and later home to the silent-film star Lillian Gish, in the 40s; the fashionable Shepheard’s nightclub, in the 60s; and the saloonkeeper Toots Shor, in the 70s. Transient guests over the years included Frank Sinatra, Muhammad Ali, the Who, Judy Garland, Led Zeppelin (who in 1973 was relieved of $200,000 from the hotel’s safe-deposit box, a crime that was never solved), Barry Goldwater, Glenn Gould, and Jimi Hendrix. It went up in 1926 and was demolished in 2007.

Now occupying the Drake’s footprint on the square block bordered by Park and Madison Avenues and 56th and 57th Streets is the 432 Park Avenue Condominium (“TALLEST RESIDENTIAL TOWER IN THE HEMISPHERE,” claims its Web site), an 85-story Rafael Viñoly–designed skyline blighter on Billionaires’ Row, whose nominal residents have included Jennifer Lopez and Alex Rodriguez, art dealer and Trump pardonee Helly Nahmad, investment manager Lew Sanders, fashion designer David Chu, hedge-funder Mitch Julis, and the Saudi shopping-mall mogul Fawaz Al Hokair.

The Drake Hotel in New York City.

It opened in 2015, and demolition commenced pretty much immediately.

At least according to lawsuits filed against the developers by the 432 Park board. And, O.K., not technically demolition. More like a robust unraveling. Complaints about “horrible and obtrusive noise and vibrations,” a “catastrophic water flood,” and a trash chute “that sounds like a bomb” going off at the very least suggest that the quality of life at 432 Park—despite the “Palladian-proportioned rooms,” private restaurant “overseen by the Australian-born, Michelin-starred chef” Shaun Hergatt, gym, spa, pool, billiard room/library, 14-seat boardroom, and views “from the Hudson to the East River, from Westchester to Brooklyn, from Central Park to the Atlantic Ocean”—isn’t all it might be. Particularly when you’ve paid $15.3 million for your 4,000-square-foot apartment, as the former J-Rod did in 2018. (They subsequently sold it.)

Certainly it would appear that the building’s Health & Wellness Center professionals charged with “maintain[ing] physical, emotional, spiritual, and mental balance” among the residents have their work cut out for them.

It opened in 2015, and demolition commenced pretty much immediately.

Despite the building’s structural issues, last summer one of the swanker penthouses, the top-floor, six-bedroom, seven-bathroom, 8,255-square-foot unit owned by Alhokair, went back on the market, listed at $169 million—twice what he’d paid for it. For that kind of money, and the people who have it, explanations about yet another pesky leak or elevator malfunction can start to wear a little thin. Blown flanges? You know what you can do with your blown flanges.

These and other annoyances that seem endemic to 1,400-foot pencil towers, such as a tendency to sway vertiginously in high wind (432 Park is so tall it needed Federal Aviation Administration approval), were reported in The New York Times a year ago. “They put me in a freight elevator surrounded by steel plates and plywood, with a hard-hat operator,” one owner told the newspaper about arriving in 2016 at her new, $17 million unit, which—surprise—turned out still to be under construction. “That’s how I went up to my hoity-toity apartment before closing.” Other residents were allegedly displaced for many months while problems were addressed.

Jimi Hendrix in bed at the Drake Hotel in 1968.

This being the world of real estate, it was only a matter of time before the legal activity began with Jarndycean earnestness. In September, the condominium’s board filed a $125 million lawsuit against the developers, CIM Group, and CIM’s co-developer, Macklowe Properties, which included the complaints quoted above, among others. In December, The Wall Street Journal reported that CIM had responded with its own lawsuit against the 432 Park board, in which it called those complaints “vastly exaggerated” and “ill-advised.”

The lawsuits sound like compelling reading. “This case presents one of the worst examples of sponsor malfeasance in the development of a luxury condominium in the history of New York City” went the board’s September salvo. “What was promised as one of the finest condominiums in the city was instead delivered riddled with over 1,500 identified construction and design defects to the common elements of the building alone (leaving aside the numerous defects within individual units).” There are references to a “shocking and disturbing” engineer’s report, “excessive fog and window condensation,” ominous “grout joint openings,” and an allegation that 35 units experienced water damage.

The board’s lawsuit also claimed that a 39 percent increase in common charges for condominium owners in 2019, partly due to rising insurance premiums, was a result of the developers’ alleged mismanagement. And by the way: “When the condominium unit owners asked about the various construction and design flaws in the building that resulted in breakdowns, failures, leaks, floods, and other dangerous and vexing problems, the sponsor engaged in a calculated, deliberate strategy to employ delaying tactics, deceptive practices, the withholding of vital information in violation of contract and ethics, and the employment of cheap, shoddy materials and methods to perform perfunctory temporary fixes to chronic serious problems in the building, leaving the building with flimsy, short-term, inadequate elements while claiming to have provided durable solutions.”

Developer Harry Macklowe, who built 432 Park Avenue.

Good stuff; that “vexing” is especially nice. Then came the CIM response, which, according to The Wall Street Journal, argued that the building was, “without a doubt, safe”—not exactly a powerhouse defense—but earned points for the alliterative poetry on display in “sophisticated symphony of systems [that] needed to be fine-tuned.” The Journal also reported that, in its response, CIM claimed that “many of the issues cited by the board have already been resolved,” that others “amount to design changes that aren’t required under city building code or the terms of the building’s offering plan,” and that, anyway, “the board had blocked its access to the building to complete those repairs, repeatedly canceled planned work at the last minute and deactivated the keys of developer representatives.”

An attorney for the board duly rebutted the rebuttal: “This is yet another attempt by the Sponsor to shirk responsibility by rewriting the record of its malfeasance.”

Macklowe himself has not replied to the 432 Park board’s lawsuit, although that might not be a grievous loss to literature. His lawyers’ response to a complaint against him by the Plaza Condominium in 2020 included passages such as “3. Denies each and every allegation contained in paragraphs ‘1’, ‘2’, ‘3’, ‘4’, ‘5’, ‘22’, ‘23’, ‘26’, ‘27’, ‘28’, ‘29’, ‘30’, ‘33’, ‘34’, ‘35’, ‘36’, ‘37,’ ‘38’, ‘40’, ‘41’, ‘42’, ‘44’, ‘45’, ‘46,’ ‘47,’ and ‘48’ of the Complaint.”

Once in Whose Lifetime?

“This … is a once-in-a-lifetime opportunity. There’ll never be another job like this one. It’s going to live on for a very long time after I’m gone,” Macklowe gushed to The New York Times in 2013. “A very long time” is a very long time, and detractors—not just of 432 Park but of all the charmless, shell-company-sustained “middle finger” developments along Billionaires’ Row—will hear that as a threat. (Reviews were, in fact, mixed: the Los Angeles Times saw 432 as “an architectural emblem of rising inequality in New York City,” but the Journal of the American Institute of Architects thought it “a refreshing alternative to the mediocrity of the buildings around it.”) Putting aesthetics aside, how does an ambitious “once-in-a-lifetime opportunity” devolve into contentious accusations of “Band-Aid” solutions and debates about arc-flash explosions?

New York D.J. Slim Hyatt at work in Shepheard’s nightclub, whose décor re-creates a well-known Cairo bar, inside the old Drake Hotel.

The briefest recap: Macklowe bought the Drake in 2006 for $418 million. That was the starter’s pistol for a decade-long gallimaufry of lawsuits, mortgages, acquisitions of adjacent parcels, acquisitions of air rights, acquisitions of partners, delays, lawsuits, deacquisitions of partners, deals with retailers, lawsuits with retailers, evictions, deals with other retailers, further delays, demolition permits, loan defaults, construction accidents, lawsuits, loan foreclosures, safety violations, lawsuits, Paul Manafort—the usual.

Excavation began in 2012. The building was completed in December 2015. Two years later, The Real Deal reported that Linda Macklowe, in the middle of her $2 billion divorce from Harry, had sued him, claiming he’d filed plans to shrink, to his personal square-footage benefit, her 78th-floor apartment at 432 illegally—the couple was to have had side-by-side “his and hers” units in the building, until things went south. (She ended up withdrawing the claim, got her deposit back, and remained at her Plaza condo.) In 2019, Macklowe married Patricia Landeau, held the reception in the “his” unit—now the entire 78th floor—and celebrated, notoriously, by displaying the newlyweds’ 42-by-24-foot photographs on a corner of the building for all the world to see, especially Linda.

It Gets Darker

One of the things the Drake is remembered for, curiously, is that in 1945, long before its over-caffeinated replacement was a gleam in Harry Macklowe’s eye, Jerome Kern collapsed on the sidewalk in front of the hotel. (The great composer died the following week of a cerebral hemorrhage.) It’s a footnote worth mentioning here because Kern and his frequent collaborator P. G. Wodehouse once wrote a song about real estate, for the 1915 musical Very Good Eddie. It was called “Bungalow in Quogue,” and its initially cheery aspirational daydream—

A helicopter flies by as the sun sets behind 432 Park Avenue.

Let’s build a little bungalow in Quogue.
In Yaphank
, or in Hicksville or Patchogue
Where we can sniff the scented breeze,
pluck tomatoes from the trees …

—soon gives way to a more cynical view:

And if we find a snail or slug
Or weevil or potato-bug,
We’ll track them down and wring their necks,
Regardless of their age or sex.

It gets darker: “When we are sitting up at nights / Comparing our mosquito bites … ” Wodehouse and Kern understood what, a century later, practically everyone involved with 432 Park would learn: even the brightest real-estate fantasies can curdle.

And so, the CIM Group/Macklowe Properties/432 Park Avenue Condominium dispute continues its voyage through New York State’s court system. For those of us who happen not to be high-end real-estate developers, or billionaires, or both, it’s hard to root for anyone here—kind of like watching Ron DeSantis and Donald Trump lock vacant eyes and paw the dirt with their cloven hooves. One just gets comfortable and enjoys the gift of Schadenfreude.

Will the eventual legal ruling see the sticky situation at the world’s 15th-tallest building as the “sophisticated symphony” of the developers’ countersuit, or more of a cacophony? And who will get the credit, or the blame? Time, measured out in a great many billable hours, will tell.

George Kalogerakis, one of the original editor-writers at Spy, later worked for Vanity Fair, New York, and The New York Times, where he was deputy op-ed editor. A co-author of Spy: The Funny Years and co-editor of Disunion: A History of the Civil War, he is a Writer at Large for AIR MAIL