Battle of Ideas, 2006 (Sven Creutzmann/Mambo Photography/Getty Images)

Billboards are sometimes the only real entertainment on a road trip, long after you’ve burned through the good CDs — and the good gossip. Most aren’t memorable, but some always catch your interest (don’t tell me Cracker Barrel has never tempted you from the roadside) and some stick in your mind due to their pure incongruity (“Oh look — you can buy barbecue and guns.”)

If you were in Havana in 2006, you would have seen a different kind of billboard erected — an electronic sign proclaiming in big red letters the differences between the U.S. and Cuba.

The sign, posted in the U.S. interests section of the island, flashed inspirational quotes, pro-democracy messages and anti-Cuba sentiment.

Fidel Castro fought back — by erecting a whole flotilla of anti-United States billboards and flags in front of the sign. He also dug up the parking lot and threatened even less cordial relations with diplomats.

U.S.-Cuba relations have been testy for years. For a long time, the U.S. has levied a trade embargo against the nation, and Americans aren’t allowed to travel to Cuba (although President Obama has lifted those restrictions a bit to let people visit family members). Cuba is a touchy subject for most politicians, because opinions on whether the United States should or should not lift the embargo and have relations with Cuba are sharply divided.

Regardless of your opinions on the embargo, it’s safe to say that the sign didn’t do a whole lot of good for our foreign relations with Cuba. In April, Raul Castro took down the Cuban billboards and last month the U.S. turned off the electronic sign, according to CNN. Only time will tell whether these small changes augur larger ones as far as diplomacy goes.

More reading:

How Communism Works
History of Cuba
Kennedy-Johnson Era