“Whether you’re embarking on new territories or finding your way home,” reads the Eastern Airlines Twitter bio, “you can always count on Eastern.”

Until recently, the airline operated four flights per week to Guayaquil, Ecuador, and two to Asunción, Paraguay, and Montevideo, Uruguay. These destinations were largely untapped by other airlines, and Eastern offered the only direct service there.

Just 16 flights per week (counting returns), and zero layovers: What could possibly go wrong?

Due East

Founded in 1926, Eastern ruled America’s skies for much of the 20th century, becoming one of the U.S.’s “big four” domestic airlines (along with American, TWA, and United) under W.W. I flying ace Eddie Rickenbacker, the company’s C.E.O. until 1959. Its glory days came and went, and Eastern eventually ceased operations in 1991.

A vintage Eastern Airlines poster hearkens back.

In 2018, Dynamic International Airways, an airline which had filed for Chapter 11 bankruptcy two years after an engine fire at Fort Lauderdale Airport injured several of its passengers, bought the rights to the Eastern name, and Eastern Airlines as we know it today was born. The logo and the planes haven’t changed much since the 80s—more on that soon—but the private company now belongs in large part to majority shareholder Kenneth Woolley, a New York businessman.

In January 2020, the company started operations, only to be temporarily shut down by the coronavirus. But the pandemic was just the beginning of a new wave of troubles for the company.

I had the misfortune of flying Eastern on December 19, on what was supposed to be a morning flight from Miami to Montevideo. This is when I discovered that the airline is among the last companies in the world that still fly passenger Boeing 767-200s, a model that dates back to 1984. Vintage cabins may sound groovy, but the reality is perilously creaky overhead-storage cabins and tattered cushions. In-seat power is “coming soon”; TVs, nonexistent.

Today’s version of Eastern.

Once all the passengers on my flight were seated, the pilot made an announcement. “Sit tight, folks,” he said. “We’re fueling the plane for departure.” After an hour of sitting tight, we were offered water. After two hours, people started stretching and walking around the plane.

Takeoff was six agonizing hours after that. But once airborne, the pilot came onto the speaker again. “Looks like our bad luck continues today. There’s a maintenance issue. Not to be alarmed.” Not long after, we made an emergency landing back at Miami International Airport with a dramatic thud—a result of six of the plane’s eight tires bursting upon landing, our pilot told us.

Firefighters hooked up emergency stairs to the plane, and the pilot gave his passengers one last farewell. “The fire is out,” he said. “Thank you. Have a good day.” This was the first any of us passengers had heard of a fire.

Eastern hostesses of yesteryear demo best flying practices.

Fifty hours later, I got an e-mail telling me to pick up my luggage at Carousel Four. By then, I was safely in Uruguay (courtesy of American Airlines, which got me to Montevideo via São Paulo), but many of the other passengers hadn’t gotten so lucky. They were stranded in Miami for five days.

Telemundo 51, a local news station, followed the stranded Uruguayans over their Florida sojourn. Most stayed at the local Holiday Inn, with $20-a-day food vouchers and none of their belongings. It was just before Christmas, and updates about whether or not they would get home were scarce.

I soon learned that what I’d suspected to be an isolated case of bad luck had occurred many times before.

By September of 2021, less than two years after re-starting passenger operations post-bankruptcy, Eastern had begun canceling flights on passengers at a rate of 28.6 percent, according to an “on-time” performance report from global travel-data provider Official Aviation Guide (O.A.G.). In December, when I flew, the cancellation rate, according to O.A.G., stood at a staggering 51.2 percent. Even considering the effects of the coronavirus, these rates are atrocious. For comparison, Spirit and JetBlue, which both also service Guayaquil, had cancellation rates of 4.6 percent and 3.7 percent, respectively.

Despite the cancellations and complaints from passengers, though, the company does refund passengers or offer them an opportunity to rebook a new flight.

But this has not stopped passengers from airing their grievances. The company’s Instagram account reads like a roster of Tripadvisor complaints. Passengers leave angry comments or emojis on nearly every post. “All flights get cancelled without notice,” one user commented on Instagram. “You find out at the airport and there NONE of their agents can help rebooking or sometimes no one is there at all.” Another: “This has to be the WORST airline service EVER.... For a 6 hour direct flight no ACTUAL food is provided!”

A Curtiss T-32 Condor passenger-transport aircraft used by Eastern Airlines in 1934.

In Uruguay, just voicing the name of the airline provokes alarm. And for good reason.

In August of last year, 140 Uruguayans were stranded in Miami after the airline cited a “crew problem.”

In October, 155 Uruguayans were stranded when the airline suspended two flights in the same week.

On October 18, Wilson Machado says he drove nearly 250 miles from his home in Chuy, Uruguay, to the Montevideo airport for his Eastern flight to Miami. “The flight simply didn’t exist,” he tells me. “It wasn’t on the monitors. No one had seen an Eastern plane anywhere. It’s been three months since, and I still haven’t gotten my money back.”

That same month, Melisa Cardozo says she arrived at the Miami airport with her 85-year-old father and was told the flight was overbooked. Her father would have to stay behind. Worse, she tells me, “I got on the plane, and half of it was empty.”

One woman aged 82 tells me she spent five hours on the runway in Miami before being told there was an issue with the pilot’s seat. Abruptly, all passengers were ordered off the plane. (She ended up taking off a day later.) Her return flight was subsequently delayed by two weeks, then a third. “Then we were told the flight wouldn’t be departing at all,” she says.

The Paraguayan influencer Tatiana Lesme took to social media in December to share her experiences with the airline. Following a canceled flight, she says it took her five days (and five trips to the airport) to get on a new flight.

“I for one wouldn’t accept a ticket if they gave it to me as a present,” Machado tells me. “It’s an abomination.” Asked to respond to passengers’ complaints, a representative for Eastern said the company is “committed to providing world-class customer service for our passengers” and cites “operational delays that all other airlines have faced” for the issues. (They add that they plan to “continue to make necessary changes to our service to best serve our passengers.”)

The travel-news Web site One Mile at a Time reports that Eastern has in the past announced new routes, sold plane tickets for them, and then canceled the routes altogether shortly after. (A representative for Eastern denies this, and says that any travel disruptions are due to “government-imposed restrictions and fluctuating customer demand.”)

Eastern, circa 1937.

Currently, Eastern is operating the New York–Guayaquil route, while at the time of this article’s publication the company Web site didn’t allow passengers to book flights on the Miami-Asunción nor on the Miami-Montevideo routes until this summer.

“There go more unhappy customers in the middle of South America during peak travel season,” one user commented on a blog post on the Airliners.net Web site. (A representative for Eastern says that the route suspensions are due to pandemic-related travel restrictions.)

These cancellations come on the heels of the company’s perplexing announcement, this past fall, of a purchase of 35 777s, which Eastern plans to use for cargo. Of the purchase, aviation expert Scott Hamilton says, “I can’t imagine for the life of me (1) how they can afford these, (2) how they can support these with internal infrastructure, (3) just where … they plan to fly them, (4) how will they compete with FedEx, UPS, DHL, and Amazon, and … (5) where they will get the pilots (you need about 10 for every one airplane).” (In a public statement released in September 2021, Eastern C.E.O. Steve Harfst said the company hoped the cargo service would “offer a nimble aircraft solution to serve customer needs” and target “customers who have struggled to find capacity in the cargo market.”)

Brett Snyder, author of the Cranky Flier aviation blog, can’t see how this would be good for Eastern. “There’s no convenience factor,” he says. “No airline wants to cancel a flight.”

Hamilton warns, “Never underestimate the prospect of incompetence.”

In the meantime, we might take a note from the Uruguayans. “Everyone,” one local tells me, “knows never to fly Eastern.”

Elena Clavarino is an Associate Editor for Air Mail