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HAVANA - He never seems to sleep—his email timestamps prove that—but when you’re trying to open a station in a socialist country where scheduled U.S. air service hasn’t existed in more than five decades, sleep isn’t a luxury one can afford.

Meet Pepe Zapata, the Delta general manager tasked with leading a team in the highly visible and daunting task of ensuring the airline’s restart of operations to Cuba goes off without a hitch.

Pepe Zapata
Ever since Delta announced it would again fly to Havana after the U.S.’s 2014 normalization of relations with the island nation, Zapata and his team have been in overdrive, making sure all goes well when three jets emblazoned with the Delta widget touch down at Jose Marti International Airport on Dec. 1.

During a recent trip to Havana, Zapata’s multiple cell phones fired off a slew of emails as he sat in the back of a hot 1970s-era Russian-made Lada with no air conditioning and an aggressive taxi driver blasting Latin jams and jockeying for position ahead of a packed city bus.

Zapata has been making the trip to Cuba nearly every week for the past year, first flying from his home in Dallas to Mexico City to connect to the island capital, and more recently hopping on regular charter flights departing from Miami. He recently worked to open Delta’s first City Ticket Office in downtown Havana—the first U.S. carrier to do so. Nearly all the equipment - laptops loaded with booking software, ticket printers and even Delta-branded balloons - had to be flown down in baggage, as little can be sourced locally and shipping to the island remains a challenge.

“Cuba has been a unique challenge,” Zapata said. “And there’s a different culture and way of doing business down here that we’ve had to carefully navigate. But through it all, the Cuban people have welcomed us and appreciated the service we’re bringing to the island after so many years of not being allowed to serve Cuba.”

With Zapata, a team of Delta experts in the region have endeavored to make the airline’s restart of operations as seamless as possible. Ingrid Hogan, Delta’s lawyer who’s made a name for herself among Cuban officials cutting through government red tape, has been instrumental in the airline’s foray into Cuba.

Delta Routes to Cuba Map
“This has been a great learning experience and a great example of the work that can be accomplished when teams from across the airline come together,” said Hogan. “More than 200 people at Delta worked to make our Cuba restart a reality and I’m excited I got to be a part of it.”

In addition to opening the first ticket office, Zapata, Hogan and others were key to getting Delta a place at the more modern, larger and more customer-friendly Terminal 3 where Delta partners Air France, KLM and Virgin Atlantic operate. The much larger terminal features familiar elements like jet bridges instead of air stairs for boarding and deplaning as well as a streamlined check-in and customs experience with designated lanes and baggage carousels on the lower arrivals level. 

Opening a new station and operating three inaugural flights on one day is likely an airline first; add to that the complexities of coordinating within strict government regulations in a country that hasn’t seen any U.S. intervention since the 1960s makes for a challenging environment. Delta ended regular commercial service in 1961.

Zapata and Hogan both recall hours-long meetings with government officials to negotiate and acquire an operating permit to fly to Cuba.

“We’re so grateful for the support of the Cuban authorities throughout this process,” Hogan said. “Every step of the way, they were willing to work with us to the extent they could and have been great partners.”

While Hogan and Zapata expect their lives to return to some level of normalcy after Dec. 1, a lot more work still must happen in Havana. Chief among them: work with travel agencies and local teams to get the word out that Delta is open for business—again.