In The Mole, the Mob, and the Meatball, Chuckles seems to have some kind of leadership position within the Toy Mafia, as new recruits have to report to him. Just what it is he does at the Toy Mafia is never made clear, and only at the end of the episode does it turn out that he has plans that go beyond that organization.
In Abe Lincoln Must Die!, Chuckles turns out to be a Secret Service agent plotting to use the position of the President of the United States to control and hypnotize the entire US. When the Puppet President is decapitated, he simply brings out Abraham Lincoln instead. When Lincoln is hit by an ICBM, Chuckles is seen buried under the rubble. At this point it is unclear whether he has survived. However, he is later seen in hell in What's new, Beelzebub?.
It is implied that Chuckles got the hypnosis technology through Hugh Bliss and that his actions were part of Hugh Bliss' Master Plan, but whether he consciously served him or was being manipulated is never made clear. It is also implied that the Toy Mafia got the technology for the hypno-bears through him and that he was somehow manipulating Ted E. Bear, but the details remain unknown.
Vegas E. Trip