I'm playing New Vegas right now as a gambler, and a RICH gambler at that. I have about 16,000 caps so far and I intend to keep going. Now, what better a way to show everyone that I'm a high roller than to earn the pimp-boy 3 billion and wear it proudly on my wrist! Problem is, the only way to get it is to side with the Omertas so they can continue buying guns from Mick and Ralph's. I also run the strip with Yes Man, and if I help the Omerta's, they'll attack the Strip and I don't want that. Is the pimp-boy 3 billion worth it?

To get the pimp boy you have to kill Big Sal and Nero, by working with Cachino in the "how little we know" quest and put cachino in charge, cachino densest try that crap.

Yeah, I believe you can side with Cachino to get it too as mentioned above.