Jailbird
/ˈdʒeɪlbɜːrd/
Definition 1 of 1
Pro Tip 1/3Negative Connotation
The term 'jailbird' often implies a negative judgment about the person's criminal behavior. 
The old town gossip referred to the recently released man as a jailbird.
Pro Tip 2/3Colloquial Use
'Jailbird' is informal and mostly used in casual speech, not in formal writing. 
At the family barbecue, Uncle Joe joked about his youth as a jailbird.
Pro Tip 3/3Cultural Perception
In some cultures, calling someone a 'jailbird' can be a serious insult. 
When she called him a jailbird, everyone knew the argument had escalated.