jail bird 

A criminal who has been in and out of prison.

This guy doesn't learn his lesson, he's such a jail bird.

jail bird by LATINFOX February 11, 2020

Jail Bird 

A female so ugly and genuinely hideous, you wouldn’t even have sex with if you just came straight out of jail.

“Yo bro you think this girl’s attractive?”
“Nah she’s a right Jail Bird!”

Jail Bird by SameSameThoDifferent August 4, 2021

Jail Bird Syndrome 

A condition in which one has feelings of attraction towards many random women, even those less attractive, due to a period of isolation from society.

Man, after finishing my final exam, I felt some major jail bird syndrome on my way to work.

Guy: dude that girl is so hot. Guy2: what?! No she isn't, you must have jail bird syndrome... get out more.

Jail Bird Syndrome by T-boneCgy August 19, 2011

Jail Birds of a Feather

A phrase that describes more Republican members of Congress. These Birds of a Featherflock together-behind bars!

Tom Delay, Duke Cunningham and Scooter Libby are Jail Birds of a Feather.

Jail Birds of a Feather by DK Sett July 1, 2007

jailbird 

Someone who consistently gets sentenced to jail time and doesn't care. If they have to do a 4 year bid they would just eat it up like its nothing. They eat, sleep, and think jail and are institutionalized. When released, they have a hard time reintegrating back into society and are likely to somehow end up right back behind bars.

Person 1: Did you hear Ramón got locked up again?

Person 2: I'm not surprised. He's a jailbird. That's all he knows.

jailbird by haanspeedball July 9, 2016

Jailbird 

A jailbird is basically someone that is so stupid that he gets thrown in jail multiple times.

How dare you call me a jailbird!

Jailbird by imaguythatknowswhatwordsmean March 2, 2015

jailbird 

SOmeone who escapes jail and is trown back in

That niggas a jailbird

jailbird by numb in balls August 20, 2003