The two soon-to-be-retirees seem uninterested in political questions. "We don't get involved in any kind of politics," Henry said. "We follow the laws here and the laws there."
They say neither was asked to spy for either side, though the men have been an important conduit for a community of families of exiles who fled Cuba and were allowed to settle on the base.
La Rosa, whose head comes up to Henry's shoulders and has an easy laugh, said people on both sides of the fence have treated them well. "They make fun of us and say we are communists over here," he said. "And when we get back over there, they say we're imperialists."
Over the years, there has been a steady decline in the number of Cubans working at the base.
As workers aged and retired, the number of commuters dwindled from the hundreds to about 50 people by 1985, according to a base newsletter, the Guantanamo Bay Gazette. By June 2005, it was down to Henry, La Rosa and two others, all earning about $12 an hour, an eye-popping salary by Cuban standards, according to another base newsletter, The Wire.
Today, most of the work once done by Cubans is performed by workers from Jamaica and the Philippines.
Leaving their homes wearing baseball caps and jackets against the cool Caribbean morning, La Rosa and Henry typically cross the fence-line as the sun rises. They eat breakfast at a house near the perimeter each morning as the military blasts "The Star-Spangled Banner" through loudspeakers.
Then, La Rosa and Henry climb into a blue pickup truck and drive to work through wide streets in a military installation that resembles a suburban anytown USA, with playing fields, a school for the dependents of service members, a supermarket-department store that resembles a Wal-Mart, an outdoor movie theater and American fast food restaurants. The base is home to about 6,000 military personnel, civilians and contractors.
It is a tranquil place, maybe even dull, where residents while away their time learning to scuba dive.
"Sometimes you feel like you are living in two worlds," Henry, a tall, slender man whose ancestors came to Cuba from Jamaica, said at the start of a recent commute. He has worked at the base 62 years. "They are two systems any way you look at it. But we're used to it."
Both Henry and La Rosa say they are looking forward to some rest after decades of what turned out to be an arduous commute.
La Rosa, who has worked on the base for nearly 54 years, said he is grateful for the work, to be able to support his family and also for the recognition from the military for his years of service.
"My co-worker and I, we never expected this," La Rosa said, his voice breaking. "It won't be easy for me to say goodbye to all these people."
Suzette Laboy reported this story in Guantanamo Bay; Ben Fox reported from San Juan, Puerto Rico.
Guantanamo Public Memory Project: http://blog.gitmomemory.org