Other People’s Postcards: Cuba

A number of years ago I acquired a small box full of postcards. A coworker and I had been discussing the PostSecret project when he mentioned to me he still had his late mother’s postcard collection. Because I love postcards, I asked Ken if he wouldn’t mind bringing them into work someday and he agreed. I was thrilled! We spent the morning going through postcards his mother received from her very well-traveled friends (Ken didn’t even have a clue as to who most of these people were). Ken admitted he was only holding onto them because the collection meant so much to his mother. He just couldn’t bear to throw them away.

So he offered them to me and I happily accepted.

I came across part of my personal postcard collection this morning. Having never really organized them before I moved to Oklahoma, I found myself pulling recent postcards sent to me from Vermont and Israel with the old ones sent to Shirley, Ken’s mother, in the 1940s and 1950s. Shirley was a teenager living in Chicago during this period and her friends, a couple named Dell and Shirl, vacationed a lot. I’m talking road trips to Hollywood and summers vacationing in their Wisconsin lake house. Dell and Shirl often drove south to Miami Beach, Florida, to visit their favorite hotel and sent Shirley postcards along the way. During one such trip to Miami Beach, the couple decided to fly to Cuba for a little sightseeing.

These two postcards went to different people – one was sent to the Strassners (also of Chicago) and the other went to Shirley (how Shirley ended up with both is a mystery). They were mailed in August of 1947, pre-Castro, and stamped from Havana with the plea, “COMPRE AZUCAR CUBANO! BUY CUBAN SUGAR!” I lost it somewhere in the disorganized pile, but there is later postcard to Shirley from the couple lamenting over whether or not to attempt another trip to Cuba. Shirl writes to her Chicago friend, “We’re not sure what to do, thanks to Castro!”

Here is a look back at American travel to Cuba, during better times:


“Dear Shirley,
Arrived yesterday about 12:00 in the evening. The ride was wonderful. This afternoon we took a plane to Cuba. All the rigamarole, you’d think we were going to Europe. Will write a letter tomorrow.”



(To the Strassners)
“Went sightseeing in Havana, Cuba, today but am going back to Miami, Fla., to-morrow. Quite hot but really beautiful.
Love, Dell”


As if reading other people’s postcards and searching the internet for more information them doesn’t make me nosy enough, I became curious to see where Shirley lived back in 1940s Chicago. The Strassners, too! Thanks to Google, I can cyberstalk and go back in time simultaneously. Both addresses are written as “Chicago 8, Illinois” – does anyone know what that means?

Shirley’s old place at 2057 W. Cermack:

Cermak St

The Strassners’ apartment at 2059 W. 21st Place:


6 thoughts on “Other People’s Postcards: Cuba

    • How interesting, thanks for finding that! I’d never come across numbers before and, in fact, my family in small town Wisconsin changed the spelling of their name to make it easier for their postman!

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