This episode starts with Whit and Tom Riley waiting at the airport for Monty Whittaker-Dowd, Whit's grandson who is visiting for the summer. But, much to Whit's surprise and dismay, Monty turns out to be a rude, spoiled brat.

After much conflict between the two of them, Whit applies a few house rules which he hopes will set Monty straight.

The next day, Whit takes his grandson to Whit's End to earn a bit of spending money. After Monty is told what to do, he waits for Whit to leave, and decides that he doesn't want to work for the money — or to be there at all! Monty calls his mom and lies about how Whit is mistreating him and demands that she pick him up immediately. Jana refuses, saying she can't pick him up for another week. Angry, Monty slams the phone down and cons a Whit's End employee to open up the cash register and give him some money. Monty then leaves for the movies, very pleased with himself.

When Whit finds out, he does not spare the rod on his grandson. Afterward, Whit explains to Monty why he had to be spanked. Monty responds positively.

After this, Monty finally starts having fun, and even joins up with The Odyssey Coyotes, completely forgetting that he ever called his mother. Everything seems to be going well until Jana finally shows up, very upset.