Try what again? Try your relationship? That's really up to you. Based on your past experiences with him, are you willing to try again?
Woof, IMO and in my experience, if they are in jail, it's jail talk. It's what they do once they get out that makes a difference. And staying clean in a halfway program, while commendable, is not the same as staying clean when you have unlimited freedom to make any choice they want. If they are in a halfway house, they are still living with pretty strict rules and regulations.
If I was you, I wouldn't make any commitments....