Scandal fascinates me. It always has.

And when someone prone to ✨ research-fueled hyperfixations ✨ discovers the restaurants that served as hotbeds for some of the greatest social, political, and economic scandals in New York’s history while reading Anderson Cooper’s Vanderbilt biography (and the entire internet thereafter), a newsletter deep dive is sure to ensue. If you give a mouse a cookie, and all that…

TLDR: For over 150 years, New York’s restaurants have served as theaters of power and social drama. They were where the most consequential political deals, financial conspiracies, and social assassinations in American history took place. Nowhere else do intimacy and hierarchy intersect so wholly as through the fundamental human act of sharing a meal. dun dun DUNNNN…

Delmonico's: Where American Fine Dining (and Financial Ruin) Was Born

Two years ago I walked into Delmonico's for the Badgley Mischka show during fashion week and it felt like stepping back in time. The lore preceded the restaurant, but it was something about the smell, the Victorian grandeur, and the secrets stained into the carpeting over the years that just made it feel monumental somehow. You could feel the ghosts of every scandalous conversation that had ever unfolded in those dining rooms. The walls whispered them.

Founded in 1827 by Swiss brothers Giovanni and Pietro Delmonico, Delmonico’s was both America's first fine dining restaurant and the unofficial headquarters for every major financial conspiracy, political machination, and social drama of the Gilded Age.

No one understood Delmonico's social significance better than head waiter, Charles Ranhofer. He served there for thirty-four years, essentially creating the rulebook for American haute cuisine as we know it (while running the 19th century equivalent of Deuxmoi or Nolita Dirtbag). Ranhofer kept meticulous records of conversations, relationships, and the social dynamics that took place at the restaurant, and his cookbook, "The Epicurean," is equal parts culinary How To masterpiece and Gossip Girl archive. The book included "a selection of receipts from 1862 to 1894," essentially creating a roadmap of who dined with whom and what they ate while plotting the course of American economic and political history.

The restaurant's most expensive dinner party was in October 1884, when Republican presidential nominee James G. Blaine hosted a lavish soirée for wealthy supporters, days before the election. The opulent affair was…wildly tone-deaf (shocking) and Democrats grabbed on to it immediately, having The New York World run a devastating front-page cartoon titled "Royal Feast of Belshazzar Blaine and the Money Kings." The cartoon depicted Blaine as a supplicant to plutocrats dining on "monopoly soup," "patronage," and "lobby pudding" while a humble laborer and his family begged for crumbs. The menu itself was circulated by Democrats as campaign material. Blaine lost to Grover Cleveland by fewer than 1,149 votes in New York (a margin so narrow that historians widely agree the Delmonico's dinner cost him the presidency).

So many other petty society scandals happened at Delmonico's over the years, but my favorite is probably the lobster story. Sea captain Ben Wenberg, a regular customer and an OG foodie, showed Charles Delmonico a “spectacular” lobster dish in 1876, hoping to have his name forever enshrined in gastronomic legend. Charles loved it and added "Lobster à la Wenberg" to the menu. Then (because…men), Wenberg got into a fistfight at the restaurant and was punished for his crass social faux pas. So, as the ultimate f*ck you, "Wenberg" became "Newberg," (just shuffled the letters) and the lobster dish has been thus known ever since just to erase Ben from culinary history.

Check out this lobster mac & cheese recipe on the Pepper App!

A Note from the Team at Pepper! 🌶️

We’re introducing REAL PRIZES with Leaderboard!

October Prizes include:
• 1st Place: $250 in groceries 💰
• 2nd Place: $100 💵
• Next 100: A ~magical~ prize (to be announced later this month…watch this space!) 🪄

Download Pepper the app to compete! 🌶️

Sherry's: The Sherry Set and Stanford White's Swan Song

If Delmonico's was where men destroyed each other financially, Sherry's was where society women perfected the art of social assassination. Louis Sherry's palatial (read: kinda gaudy) restaurant on Fifth Avenue looked like Versailles had a baby with Tiffany & Co., but it did quickly become the headquarters for the most exclusive social circle in American history thus far.

The "Sherry Set" were the original mean girls. Karens set out to destroy your reputation with a single raised eyebrow and well-worded comment about your…hmm…dress. They gathered in the infamous Swan Room to determine whose families were reputable enough to be invited to the season's most important balls, who should marry whom, and titter over falls from social grace. Beyond populating the class rank pecking order, Sherry’s is also where factory owners would gather to decide which safety regulations to ignore, which inspectors to bribe, and how to maximize profits while workers died in their factories. The Triangle Shirtwaist Factory fire that killed 146 people in 1911 happened because of lethal cost-cutting decisions made in rooms like these.

Sherry's darkest story was c/o renowned architect, Stanford White, however. White used his social position to exploit young women, and Sherry's upstairs rooms provided the perfect cover for his predatory behavior. His murder in 1906 by Harry Thaw (whose wife, actress Evelyn Nesbit, had been one of White's victims when she was 16) was the violent conclusion to years of abuse enabled by establishments like Sherry's, where powerful men could conduct their affairs behind closed doors while society turned a blind eye.

Check out this scallop recipe on the Pepper App! (and here’s a wild fun fact about them because why not??)

Sparks Steak House: Because this List Would be Incomplete Without Mentioning the Mob

On the evening of December 16, 1985, the Gambino crime family boss Paul "Big Paul" Castellano and his underboss Thomas Bilotti arrived at Sparks Steak House on East 46th Street for what they thought was a routine dinner meeting….they never made it inside.

Castellano was shot six times in the head, Bilotti four times. The hit took less than a minute as they were exiting their car and the gunmen vanished into the holiday crowds on Second Avenue.

John Gotti, "Dapper Don," sat in a car across the street watching the whole thing unfold. After the shooting, Gotti's car drove slowly past the bodies to confirm both targets were dead before heading back to Brooklyn. By New Year's Eve, Gotti had consolidated power and become the new boss of the Gambino family.

The motive went deeper than ambition. Castellano had become an out-of-touch boss who ran the family in silk robes from his 10,000-square-foot Staten Island mansion. He was more interested in white-collar crimes than traditional rackets and had banned drug dealing all together. Gotti craved a return to the roots.

He managed to evade conviction for years, earning his "Teflon Don" nickname as charges failed to stick, but in 1992, Gotti was finally convicted of orchestrating the Castellano murder among other charges. He died in prison in 2002. Sparks Steak House is still open and serving its famous porterhouse steak.

Check out this porterhouse recipe on the Pepper App!

Elaine's: The War of the Wits

For nearly five decades, Elaine's on the Upper East Side was the unofficial headquarters for New York's literary establishment and the site of some of the most spectacular ego battles in publishing history. Proprietor (legend) Elaine Kaufman facilitated it all by curating a nightly salon where Norman Mailer arm-wrestled younger writers (yes, literally), Woody Allen hid in corner booths, and Joan Didion judged from the corner.

The restaurant's most infamous incident involved Mailer, who once began unscrewing light bulbs during dinner service (no one knows if he was rip roaringly drunk, doing some sort of performance art something or the other or just generally a menace…probably all three tbh). Kaufman tossed him out, but that wasn't their only battle. When Mailer sent her an unflattering letter about the restaurant, Kaufman returned it with a single word scrawled across the top: "BORING." (like I said…LEGEND) He showed up a few days later, tail between his legs.

The real drama at Elaine's was subtler and far more devastating, taking after its Gilded Age forefathers. Kaufman wielded seating assignments like a weapon, and in the literary world, where you sat determined whether you mattered. The "family table" in the center of the room was reserved for the anointed; Plimpton, Talese, Vonnegut. Being relegated to the back meant your career was over…or at least that Elaine (legend, queen, proprietress) thought it should be.

The restaurant became infamous for its terrible food (basic Italian fare that regulars openly mocked) and its $5 lights from Little Italy, but nobody came for the ambiance. They came for Kaufman, a chain-smoking Jewish-American from the Bronx who fed struggling writers for free and then held their debts over them once they made it big. Winston Groom ran up thousands of dollars in tabs before Forrest Gump hit; she waited patiently and collected every penny.

When Kaufman died in December 2010, the restaurant closed within months. As new owner Diane Becker explained, "there is no Elaine's without Elaine." The space that had witnessed decades of literary feuds, publishing dramas, and late-night debates couldn't survive without the woman who'd orchestrated it all.