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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
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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 

SOmeone who escapes jail and is trown back in
That niggas a jailbird
jailbird by numb in balls August 20, 2003

Jailbird 

A person with many alter egos and whom doesn't know shit. Never believe what Jailbird tells you because it's most likely wrong.

Could also be a name for someone that enjoys fucking animals. Hence, the JailBIRD nickname.

Alter-Egos/Nicknames: Jubbardio, Jubbark, Jubbarkio, JJ
brown kid: hey, I heard you like wiener.
black guy: WHAT! WHO THE FUCK TOLD YOU THAT NIGGA?!
brown kid: Jailbird...Brrrrahh
black guy: Jailbird don't know shit.
Bryce: Sup zood?
Jailbird by nadjask February 14, 2009

Jailbird 

Jailbird is a term used in southern cape breton, which is based on a 40 year old drunk, contraband smoking fuck up. The characteristics of a jailbird are the following...cheap, lazy, do anything to make a quick dollar, enjoys his liquor, or is down right fucked in the head.
Holy Fuck, you fuckin' jailbird, you wouldn't let me bum one smoke off you.
Jailbird by Shayne Porno December 6, 2006

jailbird 

A really hot girl that is under 18 so if your caught having sex with her you go to jail.
Ashley is wicked hot. But she is a jailbird so she's off limits
jailbird by Pimp daddy flexxx September 13, 2005

jailbird 

The Juniors class theme for intermurals!
The Juniors at my high school are all jailbirds for intermurals! We should have been Jailbait Juniors instead!
jailbird by SparklingToros16 March 19, 2004