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The smart, educated, and quirky Miles Ledbetter (Darrin Luginski) thought his life was complete as he rose to the top of the Keister Financial Institute, working as a personal assistant for the larger-than-life CEO of the company, Edward A. Keister (Chris Harrison). He was even fortunate enough to work alongside his best friend, the charismatic Harold Jackson (Raheem Mitchell). Everything crumbled for Miles and Harold the day their boss, who was indicted for racketeering, money laundering, and tax evasion, pinned the crimes on them. It was the completely innocent Miles who ultimately took the fall and spent 2 years in prison for his boss's crimes, and though Harold escaped prison, his reputation was ruined. After being released from prison, Miles finds himself jobless, homeless, and hopeless. Miles reunites with his cohort Harold, who is now homeless as well after many failed attempts to repair his reputation. Life is seeming hopeless, until the day Miles meets seven year old Teddy Dukes (Joshua Protzmann) in the park. Teddy, who is struggling in school is in big trouble with his school's vice principal, Mr. Billieaski, and with his Mom, Grace Dukes (Katelyn Rydzewski), who is demanding a conference with Mr. Billieaski. Teddy knows there is no way out of his predicament, unless he can recruit the now homeless Miles to pose as his vice principal, but will Miles take the job?