Jailón
A rich kid, a posh one — La Paz's word for the moneyed set, from English "high" with a Spanish augmentative bolted on.
Related lesson: Bolivian Spanish: A Survival Guide.
Hear it in context
La Zona Sur está llena de jailones.
The Zona Sur is full of rich kids.
¿Y desde cuándo tan jailona vos?
And since when are you so posh?
No seas jailón, tomate tu api como todos.
Don't be so grand — drink your api like everyone else.
What It Actually Means
A jailón (feminine jailona) is someone rich — and, more to the point, someone visibly performing it. The word is a noun and an adjective at once, and it comes with a whole abstract noun, jailonería, for the world such people move in. It is not admiration. Bolivia files it in the same drawer Spain keeps pijo in, Mexico fresa and Argentina cheto: money plus display, minus taste.
Where It Comes From
From English high — as in high class, high society — hispanised to jai- and given the Spanish augmentative -ón, the suffix that turns a thing into a big loud version of itself. The spelling has never settled (jailón, jailon, occasionally hailón), which is what you would expect of a word that arrived by ear rather than in print.
How Natives Use It
Mostly in La Paz, mostly with an eye on the Zona Sur, and mostly by people who are not jailones. It attaches to accent as much as income: a jailón is heard before he is priced, in the vowels, the English loanwords and the studied boredom. Bolivians who are comfortably off use it about themselves as a joke — “perdón, momento jailón” — which is the safest way for anyone else to use it too.
Common Pitfall
Don’t mistake it for a neutral synonym of rico. Said to someone’s face without an existing friendship it lands as a class accusation, not a description, and Bolivia’s class lines run alongside its ethnic ones — see colla for why that matters. If you simply mean wealthy, say tiene plata and leave the jailonería out of it.