I’ve been told that it also means a simple stint in jail now.
It may also mean that he was raped in prison.
http://www.urbandictionary.com/define.php?term=teardrop+tattoo
Isn’t that special.
So either he killed someone, or was raped in jail, or is someone who marks the occasion of jail with a tattoo.
Wow, this guy is quite a catch. Ladies, you better catch him while you can.