Gilded Age New York had more than its fair share of outlandish rich people. Take Evander Berry Wall, whose crazy fashion choices (including thigh-high patent leather boots for him and bespoke collars and ties for his dogs) earned him the nickname "King of the Dudes." Then there’s C.K.G. Billings, the industrialist who hosted a dinner party on horseback in a Fifth Avenue ballroom, during which guests drank champagne through rubber tubes. And let’s not forget Alva Vanderbilt, who went ahead and founded the Metropolitan Opera when she couldn’t secure a private box at the Academy of Music. But there is perhaps no high-society New Yorker who was as consistently and astoundingly eccentric—or as influential—as James Gordon Bennett, Jr.

The son of a fabulously wealthy newspaper magnate, Bennett makes the trust fund kids of today look positively tame by comparison. From epic yacht races and colorful journalism to naked carriage rides and public urination, the man did it all. It’s no wonder that “Gordon Bennett!” became a British slang exclamation of shock and awe.

THE BEGINNINGS OF THE HERALD

James Gordon Bennett, Sr., a Scottish immigrant, founded the New York Herald in 1835, building the paper from the ground up. Within 10 years, the Herald had become the most widely read daily in America, thanks to its cheap cover price, up-to-the-minute news, and blatant sensationalism; Bennett Sr. once told a young staffer that “the object of the modern newspaper is not to instruct, but to startle and amuse.”

The elder Bennett’s fellow New Yorkers didn’t take too kindly to all the gossip-mongering; angry crowds regularly gathered outside the Herald's headquarters to the point that Papa Bennett kept a cache of weapons secreted behind the walls of his office—so it’s no surprise that he sent his son away to be educated in Paris.

‪Bennett Sr. continued to run the paper throughout the first half of the 19th century, sensationalizing the news while also pioneering the way it was reported. In 1836, he published what many historians believe was the first newspaper interview ever (the subject, naturally, was the madam of a brothel). So by 1886, when Bennett ceded editorial control of the paper to his then-25-year-old son, the Herald was well established.

THE LUCKY OWL

Bennett the younger first arrived on the New York scene as a teenager. Commanding a luxury yacht (courtesy of dad), he distinguished himself in the boating world at an early age and, at 16, became the youngest ever member of the New York Yachting Club. He took his ship to battle during the Civil War, spending a year at sea in the service of the Union. Legend has it that one night on the water, the warning hoot of an owl woke a sleeping Bennett and prevented his ship from running aground.

Whether the story is true or not, it was the catalyst for a lifelong obsession with owls. Bennett could not get enough of the predatory birds: he ran editorials on species preservation in the Herald and collected owls (both live and statuary) throughout his life. When he commissioned renowned architect Stanford White to design a new Herald building in the 1890s, it included plans to have the roof lined with bronze owl effigies—26 of them—whose eyes flashed at regular intervals with electric light.

Though the building was demolished in 1921, two of the owls now flank the Minerva statue (which also began life on the building’s roof) that stands in modern-day Herald Square—and their eyes still glow a ghostly shade of green.

YACHT ROCK

There’s a reason why Bennett’s nickname around the NYYC was “The Mad Commodore.” Though he engaged in every rich-boy pastime under the sun—polo, ballooning, tennis—his lifelong passion was yachting. He won the first-ever transatlantic yacht race in 1866, guiding the Henrietta on a two-week voyage from the New Jersey coast to the Isle of Wight. Aboard his next vessel, a steam yacht called the Namouna, he entertained artists, painters, bon vivants, and even a very young Winston Churchill.

But they were all outdone by the Lysistrata, a 300-foot monster with such onboard amenities as a Turkish bath, a milk cow in a fan-cooled stall, a theater troupe, and a luxury automobile—which he drove across Bermuda in 1906, marking the first car ever to touch the island’s soil. His joy ride earned him the enmity of two prominent vacationers: Mark Twain and a pre-presidential Woodrow Wilson, who campaigned to have cars banned from Bermuda after they saw Bennett roaring around in his De Dion-Bouton.

It wasn’t all fun and boat cows, however. Bennett kept up his publishing duties throughout his life, rising at the crack of dawn to run the Herald via letters and articles cabled to him by his editors.

WHIZZER ABOUT TOWN

To say that Bennett lived it up would be an understatement. His partying ways were infamous, fueled by a seemingly infinite store of funds and a flair for the dramatic. One of his hobbies included driving a coach-and-four at breakneck speed through the streets—often in the wee hours of the night, and often in the buff. (He once ended up in the hospital after driving under a low archway in Paris and clocking himself on the head.)

Bennett was also a cocktail enthusiast, and his boozing landed him in a heap of trouble one notorious evening in 1877. The story goes that on New Year’s Day, the publisher got rip-roaring drunk, stumbled into a fete being thrown by the family of his then-fiancée Caroline May, and proceeded to urinate into the fireplace in front of everybody. The engagement was called off, but that wasn’t the end of it: Caroline’s brother, Frederick, attacked Bennett with a horsewhip the next day, and later challenged him to a duel. Pistols at dawn were considered archaic by the 1870s, but that didn’t stop Bennett and May. As luck would have it, both of them were such bad shots that they completely missed each other, and that was the end of that.

Which isn’t to say that Bennett wasn’t mortified by the whole incident. Shortly afterwards, he left New York in shame and spent most of the rest of his life in France and traveling the world aboard his many, many yachts, and eventually founding the Paris Herald. He also maintained lavish houses in New York, Newport, Paris, the French Riviera, and Versailles—in one of Louis XIV’s chateaus, naturally, where he played host to kings and dukes.

PAY DIRT, I PRESUME

Though Bennett lived in the lap of luxury himself, he funded the exploits of adventurers willing to get their boots dirty. Most prominent among them was Henry Morton Stanley, a regular correspondent for the Herald and legendary explorer. In 1871, Bennett bankrolled Stanley’s expedition to track down a beloved Scottish missionary, David Livingstone, in the jungles of Tanzania. And naturally, he traveled in style: an armed guard, 150 porters, and 27 pack animals, while a man in front carried the flag of—what else?—the New York Yacht Club.

Stanley tracked down his target after a six-month trek, at which point he allegedly uttered the famous line: “Dr. Livingstone, I presume?” Livingstone wasn’t actually missing, per se, but it sure made for a good story—and one that sold a lot of newspapers.

So did the next epic journey that Bennett funded, though it proved to be far less successful for the explorers themselves. Bennett backed an 1879 expedition to the as-yet-undiscovered North Pole, led by U.S. Navy vet George Washington De Long. But the trip ended in disaster when De Long’s ship was crushed by ice in the Bering Strait, and the surviving crew was forced to trek overland. Only 13 made it back to civilization in Siberia, while 20—De Long included—perished.

THE MAUSOLEUM THAT WASN’T

As Bennett aged, his affinity for the insanely opulent never waned. He went back to Stanford White (who, besides being a prominent architect, was also Bennett’s drinking buddy) with an idea for his final resting place: a 200-foot-tall mausoleum built in the shape of an owl, to stand on a promontory in Washington Heights. Inside the owl, a spiral staircase would lead visitors to the bird’s eyes, which would be windows offering sweeping views of the city. When Bennett died, his body would be placed in a sarcophagus and suspended from the ceiling on chains, to dangle in the middle of the monument.

But Bennett’s ridiculous tomb never came to be. In 1906, White was murdered by his lover Evelyn Nesbit’s millionaire husband, resulting in a lengthy court case that the media (the Herald included) dubbed “The Trial of the Century.” Bennett scrapped his plans for the giant owl, depriving New York City of what could have been its weirdest landmark.

LAST COMES MARRIAGE

Though Bennett was a notorious playboy, he eventually did settle down—at the ripe old age of 73. His wife was Maud Potter, the widow of George de Reuter (of Reuters news agency). They were married until Bennett’s death five years later, when he passed away at his villa in the Riviera in 1918.

Sadly, Bennett's paper followed him to the grave; the Herald was sold off in 1920 and was absorbed into an amalgam that became the now-folded New York Herald-Tribune.

But perhaps Bennett always knew his baby was doomed to die with him. When he moved the Herald building uptown, he only signed a 30-year lease. When an underling questioned this decision, he was quickly told by the mercurial publisher that, “Thirty years from now, the Herald will be in Harlem, and I’ll be in Hell!”

Here’s hoping Bennett’s having an entertaining eternity down there in the inferno; otherwise, after a life like that, he’d get terribly bored.