Jail or Cheiron's Academy

Iolaus used to be a thief, until he was caught. He was offered a choice: Jail or Cheiron's Academy. Iolaus often struggles to make enough money for tuition and get passing grades to avoid having to go to jail.

1.02 Between Friends

Iolaus: I borrowed that money - from Nysus.

Nysus/Strife: From me? Iolaus, everybody knows I don't have that kind of money.

Iolaus: Nysus! Come on! This is no time to joke around. I'm already here on probation. They'll bury me!

1.04 Herc and Seek

Cratus: Well, the way I see it - I'm the reason they gave you the choice between goin' to jail and joining the academy.

Iolaus: Ah, they couldn't prove anything.

Cratus: That's because I didn’t talk. So I figure you owe me.

1.06 Teachers Pests

Iolaus: So I was, uh, thinking I might, uh, sneak out.

Jason: Are you crazy?
Hercules: You get caught, and you'll get kicked out of school.
Iolaus: Well, if Kora fires me, I can't pay my tuition anyway. The thing is - I need you guys to cover for me.
Jason: You gotta be kidding, Iolaus.
Hercules: Ah, I don't think so, you know?

Iolaus: Don't you remember why I'm here? Probation. If I'm not in the academy, I'm in jail. I’m going to Kora's, whether or not you help me.