Got some Questions who helps a little if answered:
Does the X360 controller operate like a HID device when it's connected to a X360 video game? or it's have a "closed-source" way of communicate?
Can the controller see the difference between a Computer and a Video-game USB connection? Does the video-game send some "extra info" that is unsent when it is controlled by Windows' Microsoft drivers?
Maybe the key to get the Chatpad working is to see the controller -> "Host Device" communication, not the Chatpad -> controller one.
redCl0ud posted some drivers for Xbox and X360 controllers, maybe we can mod his work to load the Chatpad.