This term derives from a Cuban word meaning street jockey. I would describe a jinetero as a hustler, but the word means so much more.
Originally the term jinetero (for men) and jinetera (for women) referred to those associated with prostitution. Today, the meaning is much wider and refers to pretty much all types of swindles.
These will be encountered in tourist areas; outside of these places Cubans will be genuine and honest, so do not prejudge everybody, especially if you have just been walking around Habana Vijea, which is notorious for them.
Now it’s all a matter of opportunity, ranging from my “brother” works in a cigar factory, to a smiling stranger approaching you in the street to offer casa particulars (especially if you have luggage with you) or deals on local restaurant or taxis.
Jinterismo is opportunism and while it’s not necessarily a criminal activity, the line can get blurred.
Imagine the scenario.
An attractive, muscular Cuban guy says to a Nordic woman, “Hello, do you speak English?”
“Yes, I’ve been living in London,” she replies.
“Oh, great, I am a student of English,” grins the Cuban. “Would it be possible to practise my English conversation with you?”
“Sure, I’m happy to help,” replies the Nordic lady.
They go to a café or bar where it turns out the guy’s English is fluent. But when the bill comes it happens to be twice the normal price, which the Cuban passes to his new friend!
When this happened to me I agreed and suggested we went to the park where it was quieter. Suddenly my Cuban friend was reminded about an appointment they needed to attend and left.
Another example would be for the guy to offer an invitation to dinner in which you pay, then the next night you may see him with another Canadian or European woman.
Now I see that as opportunism rather than criminal activity.
This doesn't just happen in Cuba, it takes place in tourist destinations all over the world, but in Cuba it is conducted with more style and panache.
People have commented to me that in bars and nightclubs Cubans will try to chat them up in order to get free drinks. Well, yes, the same has happened to me, in Cuba and in other countries, but Cubans seem to be judged particularly harshly. It’s pretty unfair.
Others have commented about jinetero in terms of the man arranging “girls for prostitution” - now I see this as pure criminality. In my mind there is nothing lower than a man selling others for prostitution. Living in Habana I have encountered these types of individuals over time. Most, if not all, of those known to me have either disappeared from public view due to me introducing them to the criminal justice system or have run in the opposite direction having seen me coming along the street.
You do not need to worry about jinetero/a, just be aware and if it sounds too good to be true, it will be - it’s not quantum mechanics.