He is a part of the richest family in town. Almost every grown-up in Westport tries to get on his good side in hopes of getting in good with his parents, who travel a lot and often leave Cooper at home. He forms a close bond with Oliver Otto, who he cares for very much, and the entire Otto family due to the fact that they treat him like a normal. He also gets life lessons from the Otto parents like their children; like having him do chores or even punish/ground him.

〈 ★ 〉 A rich teen from Westport

Oliver is snobby, sarcastic, and materialistic. He is excessively concerned with material possessions, such as money. He is extremely business savvy and looks up to people who trade and are rich. Furthermore, he often makes sarcastic comments when speaking to people, especially family members. Despite all of this, he still cares for and looks after his family and friends. He is particularly kinder to his boyfriend, Cooper Bradford than his family.