I had to reload after slipping Benny a stealth boy and bobby pin. I would have made it out, but I got stuck in a wall by the weapon crates. What I'm wondering is if Benny makes it out in this situation. Sure, he had a Stealth Boy, but so did I and it didn't stop every guard from seeing me and shooting at me on the way out.

So, does he make it? Because if not, it's not worth pissing off Caesar and loosing my shot at the lucky shades. I might as well take him in the arena.

Taken from the wiki: "Benny can also be untied by the Courier, at which point he will flee Caesar's tent and disappear from the game."

I read that, but I get the impression he doesn't make it out alive, even with the Stealth Boy. I made a beeline for the exit and used about a half dozen stims on the way. If they saw me, then I don't see how they didn't see Benny.

Thats because Benny is an NPC, therefore pretty much invisible to other NPCs when using a SB.

EDIT - http://www.youtube.com/watch?v=hUkwrb2RUc0&feature=channel_video_title