Jackson was a very well behaved kid, in contrast to his sister. One day he found Slappy in his suitcase after visiting his Grandpa Whitman. Soon, Slappy starts controlling Jackson and forces him to do bad deeds.
Slappy controlled him using a chip from a game Jackson played but even after Jackson discovered this, Slappy was able to use the chirp from a canary. Jackson ruined things for the Youth Center he volunteers for and was grounded for all of his evil actions.
He discovered that Rachel was working with Slappy the whole time and when they heard him eavesdropping, he heard the chirp again, meaning he might be permanently under Slappy's control.
Jackson is twelve years old, Caucasian, short and thin with straight brown hair, brown eyes, freckles on his nose and dimples when he smiles.
Jackson has always been a gentlemanly kid who knows that it is easier to be good than to be bad. He tries to be nice to everyone, work hard in school, be cheerful and kind, help people when he can and just be a good person. This has earned Jackson a good reputation and he has always been every parents' dream.
Unfortunately, Jackson is often teased by his friends about his reputation, and this has given him a bad relationship with Rachel. Jackson and Rachel dislike each other because of their opposing personalities and Jackson has always had his sister being in his face and trying to get him into trouble. But Jackson hardly ever let Rachel bother him in the least.
But after Slappy's control over him, Jackson's reputation is damaged beyond repair and he feels that his life can never be the same again.
- Jackson is one of the few protagonists to get controlled by the main antagonist, another being Beth from Horrors of the Black Ring.