Monday, September 10, was looking to be a miserable day, with torrential rain and wind. The day before, Australian tennis upstart Lleyton Hewitt had aced American Pete Sampras, and, on Saturday, Venus Williams had beaten her sister Serena in the finals of the US Open. But the city was looking forward, waking up to the first full week of school and the next day’s mayoral primary election, in which Public Advocate Mark Green was in a heated race with Bronx Borough President Freddy Ferrer for the Democratic ticket, and the few Republicans in the city were entertaining the prospect of financial services billionaire and political newbie Michael Bloomberg as mayor of New York.

Green, Ferrer, and Bloomberg raced around the city, shaking hands and slapping high fives with New Yorkers while their staffers and volunteers filled crowds, waved signs, and shouted slogans. About 20,000 people were getting excited to see the second Michael Jackson show at Madison Square Garden that night; the king of pop was mounting a comeback, and the show was rumored to include a galaxy of special guests after his Friday-night concert, in which Marlon Brando, Whitney Houston, Britney Spears, and Elizabeth Taylor, among others, performed or spoke.

A different sort of congregation gathered at the morning rededication of fire station Engine 73, Ladder 42 in the Bronx, where Mayor Giuliani cut a ribbon and said a few words. Before the mayor spoke, Father Mychal Judge, a fire department chaplain, gave a homily.

“Good days. And bad days. Up days. Down days. Sad days. Happy days. But never a boring day on this job,” Judge said, moving gently in a white frock among the firefighters and their families. Most just knew him as Father Mychal, but Judge was pretty unusual, a gay recovering alcoholic who had lovingly administered to a more diverse set of New Yorkers than perhaps anyone else wearing the cloth. He was typically affective that morning. “You get on the rig and you go out and you do the job, which is a mystery. And a surprise. You have no idea when you get on that rig. No matter how big the call. No matter how small. You have no idea what God is calling you to.”

In the World Trade Center plaza, dancers were doing a run-through of the performance they’d be giving the next day on the Evening Stars stage that had been set up at the foot of the North Tower, facing the Sphere, the 25-foot-tall golden globe sculpture that had anchored the plaza since it was opened in 1971. The performance was the end to the World Trade Center’s free summer outdoor entertainment schedule, which had featured acts including Celtic dancing, Odetta, and Herman’s Hermits. But the dance rehearsal was called off when the sky unloaded buckets of rain.

Downtown, at Windows, a new beverage manager, Steve Adams, had just been promoted and was working his first day while the beverage director, Inez Holderness, was home in North Carolina for her sister’s wedding. Adams was a devotee of English ritualistic Morris dancing and came from a small wine store in Vermont and had finally, at 51 years old, found a foothold on a career path he was proud of. He had always been the guy who was passed over. Now, here he was, entrusted to run the stocking and distribution of the wines and other beverages for the top-grossing restaurant in the world.

Managers were expecting a light night because it was a Monday and it had been raining buckets throughout the day. Lunch service was pretty quiet: several dozen guests. Captain and sommelier Paulo Villela broke down the buffet table—the same one that Joe Baum had Warren Platner design in 1976—with his supervisor Doris Eng. The two placed the trays of salads and shrimp and breads on enormous Queen Marys, the stainless steel, multi-shelved banquet carts that roll on wheels. A lot of the food was thrown out, but staff made plates of the good stuff for themselves to eat later.

Villela had been a manager at a restaurant on the Upper East Side, but he applied for a captain position at Windows in 1996. There wasn’t one available, so he came back several times until he was offered a newly created position, a cross between a busser and runner. Villela took it.

Closer to midnight, a few parties were unwilling to let the night end.

He quickly moved up to being a captain and had been spending his time off working in the cellar and taking wine courses until he became a sommelier. He was making 130,000 dollars a year. And Villela’s 19-year-old son, Bernardo, joined him at Windows as an assistant cellar master.

As Villela and Eng, with a couple of busboys, moved the food to the Queen Marys, they joked about her role as a manager and how he used to be one. Eng said that, to Chinese people, being a server was the highest place one could rise to before going to heaven. The conversation continued into her office.

General manager Glenn Vogt had been in a two-hour meeting with David Emil, restaurant comptroller Howard Kane, and a few others to discuss Windows’ New Year’s Eve party. It was the first meeting, so it wasn’t stressful, more exciting to be brainstorming what they hoped to do that year.

After the meeting, Vogt went to the office he shared with assistant general manager Christine Olender to review what had been said. Michael Lomonaco wandered by and mentioned that he needed his glasses fixed but that his opthamologist was out of town. Lomonaco was going on a trip to Italy soon. Chefs can be obsessive list-makers. He wanted to get the glasses checked off his list, so he made an appointment at the LensCrafters in the concourse downstairs for noon the next day.

Lomonaco had just returned from shooting Epicurious for the Travel Channel the week before. He was getting up to speed for the busy autumn season of events and weddings, drawing up the new fall menus, and hiring people, one of the most important being a replacement for his executive pastry chef, Heather Ho, who had given her notice in August. Ho had just started in June, but she didn’t like working at Windows. On that Monday, Ho talked on the phone with her best friend from high school. “I don’t know when I am going to get out of here,” she said. “I have to wait. I can’t burn any bridges.”

Vogt had a meeting with Paulo Villela, because the manager wasn’t happy with the number of hours Villela had been clocking. Ninety-four hours in the last week was way too much overtime. But Inez Holderness was away, and she’d asked Villela to help. Villela had come in early that morning, he was going to work late that night, and he planned to come in the next morning to help Steve Adams, the new beverage manager, in the wine cellar.

O’Neill had had his FBI retirement party at Windows. That night, he told a friend that a terrorist attack was coming soon.

“If you don’t want me to work so many hours, I won’t work tonight,” Villela said angrily before storming out of Vogt’s office. He told Bernardo that he should not come to work the next morning either. It was, after all, Villela’s younger son, Felipe’s, eleventh birthday; they could see him before he went to school and then go to work in the evening.

The office day was wrapping up, and Olender headed over to the cubicle of Doris Eng, the Club manager; they were both single women living in the big city and were equally devoted to their parents. Eng lived with her mother in Flushing, Queens. And Olender was on the phone practically every day with her parents back in Chicago. The two had gone on vacations together and had recently celebrated Eng’s 30th birthday.

Both women were tough, even if Olender was a girly-girl who wore fancy, impractical shoes. She was Vogt’s gatekeeper, so if you needed him to sign off on something, she was your best friend. But when Vogt wasn’t around, Olender was in charge, and the staff respected her.

Eng wore a jade-pig necklace—she was born in the year of the pig—and practical shoes, because she stood all day and her feet often hurt. Eng had a wry sense of humor, would joke about “the Asian way,” and would sometimes laugh about the most inappropriate things. That day, she was looking online at shoes to buy. Olender ribbed her about the shoes she had selected. Both women came to work early and left at around five in the evening. Eng could often be at her desk as early as 6 am getting ready for the opening of the club breakfast.

Because of the construction on the new wine cellar and bar, breakfast was being served in Wild Blue. Everything was a little out of sync, so Eng asked Villela if he could help her with breakfast, but he was leaving the building in a huff and said he couldn’t. Olender offered to help Eng with the morning setup before Olender had a meeting with Vogt at nine.

Jules Roinnel surprised them with the news that he wasn’t going to be coming in for pre-meal. You could count on two hands the number of times in the past two decades that he had worked dinner, but he had been upstairs on 107, where restaurant director Melissa Trumbull had asked him to work with her during Tuesday evening’s service. “I have no one on the floor with me,” she said. “Come on, why don’t you work it? You can have the floor or the door. And we can have dinner together. I’ll even let you pick out the wine.”

Trumbull often teased Roinnel about his wine choices. He accepted her offer and said he’d take the door—an easier gig—and looked forward to the next day. With only 240 reservations registered for the night, it should be manageable.

“I’ll see you at 3:30,” Roinnel said to Eng and Olender, leaving at 5 pm.

Dinner service began at the usual five. Despite it being a Monday and there being limited visibility, more people than expected were coming for dinner. The waiters were feeling good; for some reason, almost every table was ordering wine or champagne, some of it on the higher price end, so the money would be good.

In the Greatest Bar, in the SkyBox lounge, George Delgado was hosting, with Dale DeGroff, a Spirits in the Sky cocktail seminar, a monthly event in which the two spoke and demonstrated for a gathering of about a dozen people who dropped $35 each for the educational merriment of mixing cocktails and drinking. Tequila was the focus that night. DeGroff was doing the gig to fulfill a contract obligation to Emil, for whom he worked at the Rainbow Room.

DeGroff signed off on what was probably the last bill of the night, well north of a thousand dollars.

Delgado’s day had started badly; his car battery had died that morning after he’d driven through the torrential rain, so he had to drop 50 bucks to take a taxi to work, all the way from Hackensack, New Jersey. The class began at 6 pm, but Delgado came in about three hours before to set up each student’s station at long, classroom-style tables, where he carefully placed the shaker kit, garnishes, juices, salt, ice buckets, and a selection of tequilas that each student would get to taste.

Delgado and DeGroff took turns demonstrating their mixology skills and telling stories, with DeGroff leading the classic margarita instruction and Delgado teaching the class how to make two of his own Greatest Bar tequila specialties, La Rumba and the spicy Bendito Loco. Also at the Greatest Bar that night, the new head of World Trade Center security, John O’Neill, was having a drink before heading to his favorite watering hole, Elaine’s, where writers and cops mingled with celebrities. O’Neill had recently retired from the FBI, where he had been the Bureau’s counterterrorism chief in Washington, DC, and was instrumental in the capture of the 1993 World Trade Center bomber Ramzi Yousef.

O’Neill had had his FBI retirement party at Windows. He was just a few weeks into the much-better-paying job. That night, he told a friend that a terrorist attack was coming soon. “We’re due,” he said. “And we’re due for something big.”

By 9 pm the sky had cleared, leaving the city wet-slicked and vivid. Closer to midnight, a few parties were unwilling to let the night end. A couple of tables for two lingered, savoring the views.

Waiter Carlos Medina was taking care of two Italian newlyweds at table number 64, facing due north. When it was time to pay the check, their credit card was denied, which wasn’t unusual for international cards. Medina offered to escort the new husband, who had invited him to visit his cheese factory back home, to the Citibank ATM in the concourse. They went all the way down and back up. “What a beautiful building,” the Italian said. But when he laid out the cash, he realized he didn’t have enough dollars for the tip. He gave Medina and his coworkers 150,000 lira (70 dollars) instead.

Captain Luis Feglia tried to adhere to the “legendary service” code that Ron Blanchard preached, so he let his guests linger. As captain, “Papi” had the discretion to tell the front and back waiters in his team to go home, so it was just he and one busboy, Telmo Alvear, who remained. Twenty-five-year-old Alvear, who had a one year-old son and whose wife was studying computerized accounting, often heard from Feglia how he should pick up as many shifts as possible to make more money. As a teen, he had immigrated from Ecuador, and just that summer he had quit a midtown waiting job to work at Windows, where the tips were better.

Alvear had added a shift for the next morning, taking another staffer’s spot. After the guests finally called for the check, Feglia and Alvear changed in the locker room and went down to take the E train to Queens. As shop steward, Feglia was coming in the next day for a ten am meeting, and Alvear would have to sleep quickly; he was expected back in six hours.

After they left, the night still wasn’t over on the 107th floor. In the bar, in the booths outside the SkyBox, DeGroff and Delgado were entertaining their students with some extra credit after the class had ended at seven thirty. One of the women students was enthralled by the music DJ Penelope Tuesdae was playing, and so they decided to stay for dinner. They had ordered small dishes, and DeGroff had ordered bottle after bottle of Veuve Clicquot for the group, tickled to be sticking Emil with the bill.

After one o’clock, Delgado suddenly remembered he didn’t have his car. It would have cost a small fortune to take another taxi back home, so he called his wife, Fran, a fellow bartender he had met working at the Greatest Bar but who no longer worked there, and asked her to put their 11-month-old baby, Genevieve, into the car seat and to take the hour-long drive to get him.

About eight people were still in their party until DeGroff asked for the check. He signed off on what was probably the last bill of the night, well north of a thousand dollars.

When Fran arrived in her Volkswagen Beetle, Delgado headed out. He saw the cleaning crews arriving and gave the security guard, Mo, short for Mohammed, a half-handshake, half-backslap on his way out before taking the elevator down to meet his family on West Street. The baby was awake, so he took her out of the car and held her in his arms and raised her slightly so that she faced the World Trade Center buildings.

“Look, Genevieve,” Delgado said, gazing at the reflection of light in her big brown eyes. “That’s where Daddy works, way up there.”

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From The Most Spectacular Restaurant in the World by Tom Roston, published by Abrams Books © 2019.