Jason is the 24-year-old grand-nephew of deceased oil tycoon Red Stevens. Accustomed to a life of privilege and entitlement, he is initially cynical, self-absorbed, and resentful of his wealthy family. Over the course of a twelve-month challenge designed by his late great-uncle, Jason engages in tasks involving hard manual labor, philanthropy, and community service. He slowly develops an appreciation for hard work, generosity, and genuine human connection.

Theodore is the 80-year-old founder of the powerful Hamilton, Hamilton, & Hamilton law firm in Boston. As the executor of Red Stevens's estate, he oversees the distribution of assets to the greedy family members before focusing on Jason's year-long challenge. He acts as both a formal judge and a compassionate father figure, carefully administering the videotaped instructions left by his deceased friend.

Margaret is Theodore Hamilton's highly competent assistant, having worked alongside him for forty years. She handles the complex logistical details of Red Stevens's estate with quiet efficiency. During Jason's monthly meetings, she acts as a stabilizing presence, offering subtle encouragement and wise counsel that helps keep the young man on track.

Howard "Red" Stevens is a deceased, larger-than-life oil and cattle tycoon who built Panhandle Oil and Gas from scratch. Realizing his immense wealth ruined his children by making them entitled, he orchestrates a unique challenge for his grand-nephew Jason. Through a series of monthly videotapes, he attempts to impart essential life values to the only relative he believes still possesses potential.

Nathan is a massive, six-foot-eight professional football player for the New England Patriots. Having grown up at the Red Stevens Home for Boys in Maine, he considers the facility and its young residents to be his true family. He frequently returns in his free time to perform chores, mentor the youths, and demonstrate the depth of chosen family bonds.

Emily is a seven-year-old girl battling a rare, terminal form of cancer. Despite undergoing painful medical procedures, she approaches life with immense courage and takes simple joy in visiting a public park. She befriends Jason and teaches him how to face severe difficulties with a positive spirit.

David is a young man with blindness whom Jason meets on a commuter train. He navigates the world with a vivid, occasionally coarse sense of humor. By laughing at the daily inconveniences caused by his condition, he shows Jason the power of humor in lightening heavy burdens.

Gus is an elderly, physically strong Texas rancher. As a longtime friend of Red Stevens, he oversees Jason's very first assignment. He puts the reluctant young man to work digging post holes and stringing fences in the Texas heat.

Jack is the eldest son of Red Stevens. Described as philandering and historically uninterested in his father's business, he inherits the massive Panhandle Oil and Gas company with the strict legal stipulation that he must never attempt to manage or control it.

Ruth is the daughter of Red Stevens. She inherits the family's Texas cattle ranch with the requirement that she keep her hands completely out of the actual ranch operations.

Bill is the youngest son of Red Stevens. He inherits his father's entire investment portfolio, but the funds are to be strictly managed by Hamilton's law firm to prevent Bill from squandering the wealth.

Brian is a young man struggling to balance his education and a job. When his car engine fails and he cannot afford the seven hundred dollar repair bill, Jason steps in to cover the cost, sparking a genuine friendship.

Josh is an older man who rode the rails with a young, un-housed Red Stevens many decades ago. Despite living in poverty, he maintained a joyful spirit by daily reciting a mental list of ten things he was thankful for.

Reggie is a private detective employed by the Hamilton law firm. He is tasked with observing Jason's progress from a distance and reporting back to Theodore Hamilton to ensure the young man is genuinely participating in the challenges.