Troublemaker by Andrew Clements

Clay Hensley is a troublemaker and proud of it. He’s only in sixth grade and already his school file is two inches thick with reports of his visits to the principal’s office. When Clay’s older brother Mitch comes home after spending a month in jail, Clay pulls his best prank ever to impress him. But his plan backfires when Mitch, having learned his lesson in prison, becomes determined to steer his brother onto the straight and narrow.

Clay is a lovable troublemaker, but it’s clear that his behavior is following a troubling escalating pattern until his brother interferes. Clay thinks his trouble-making is all in good fun, and it’s not until his brother makes him promise to stay out of trouble and get good grades that he begins to realize maybe it was fun for him, but what about all the kids he picked on?