In 1991, a lone Russian-built MiG-21 approached the Florida coast from Cuba. The plane began "wagging" its wings, a recognized signal for friendly intent. The pilot was Orestes Lorenzo, and he was bringing the MiG to the United States in an attempt to defect from Cuba. The only problem was his wife and kids were still in Cuba.

Not for long.


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That's the thing about fighter pilots – no one will accuse them of being timid. Lorenzo was no different. He did fly a 40-year-old MiG straight at the coastline of the world's lone superpower. In fact, Lorenzo was so daring, he wasn't even in the Cuban Air Force when he took the jet. He told American officials he'd "borrowed" it to make the flight. Lorenzo didn't even speak a word of English, he just yearned for freedom.

While he was in Cuba's Air Force, he learned to fly in the Soviet Union and was deployed to fly air missions in Angola. After a second tour of duty in the Soviet Union, he and his family moved to an air base far from the Cuban capital of Havana. They found themselves unhappy with their situation, facing poverty, repression, and a government more concerned with itself than its people. Lorenzo and his wife hatched a plan to escape with their children, but it was only Lorenzo who landed at Naval Air Station Key West that day in 1991.

That's where his daring comes in. Lorenzo was whisked away to Washington, where he was (presumably) debriefed, and received his asylum paperwork, as well as visas for his wife and two sons. All was almost set to go as planned, except now the Cuban government wouldn't authorize his wife and children to leave the island nation. Orestes Lorenzo didn't just accept his station in life like Castro wanted him to, and he sure as hell wasn't about to accept this. Lorenzo launched a PR campaign that culminated in President George H.W. Bush giving a speech directed at Cuba, imploring Cuba to let his family go, all to no avail.

Castro refused, so the fighter pilot took matters into his own hands.

Spoiler alert: fighter pilots are brave.

Lorenzo raised $30,000 to purchase a 1961 Cessna 310, a small, simple civilian aircraft. He even took lessons to learn to fly the Cessna like an expert. He got word to his family that they should be in a certain spot they all knew well, wearing orange t-shirts. At 5:07 p.m. on Dec. 19, 1992, Lorenzo took off from the Florida Keys in his 30-year-old Cessna and flew just 100 feet above the ocean.

Flying up above a set of cliffs on Cuba's coastline, some 160 miles from Havana, he pulled up and saw three bright orange t-shirts waiting for him by the side of a road. He landed the plane, got his family inside, and took off again, headed for Marathon in the Florida Keys. Two hours later he and his family were safe.

The Lorenzo family lands in Marathon.

The U.S. returned the MiG to Cuba, and the Lorenzo family settled in Florida, starting a concrete business. Very few Cuban pilots were able to defect to the United States during the entire Cold War.