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Meeting David Wilson is a feature length documentary about the enduring legacy of slavery in today's young black society. David Wilson, a 28-year-old African-American journalist, travels into his family's past to find answers to America's racial divide. Along the way, he meets another David Wilson, the descendant of his family's slave master. This discovery leads to a momentous encounter between these two men of the same name but whose ancestors were on the opposite sides of freedom. The film first observes Dave as he revisits his upbringing in the gritty streets of Newark, New Jersey and how this negative environment stirred his desire to uncover the truth about his family's past. Through genealogical research, he discovers his roots are steeped in slavery in North Carolina. On the plantation where his ancestors were slaves, he finds that the "Big House" is still intact and owned by a direct descendant of his family's slave master. David decides to travel to North Carolina to meet this other David Wilson - a southern, white conservative. On his trip south, David faces difficult questions about the current state of Black America and its relation to the legacy of slavery. Upon arriving to North Carolina, David prepares himself for this historic meeting by revisiting the lives of his ancestors. David spends a day "pulling" tobacco, visiting the church his great grandfather founded right out of slavery, and his family's run down slave quarters. David finally confronts his white namesake and asks pointed questions that lead to a dynamic and unique dialogue concerning slavery, religion, and reparations. They explore the history of the Wilson name in both the white and black families and walk the grounds of the old plantation. Curious to learn if they have more than a name in common, Dave tests his DNA. One of the results of this test identifies his African origins. Once this match is made, the lab provides David with a name and location of an African ethnic group so that he can travel back to Africa to complete his journey. One of the film's emotional apexes is a family reunion in which David brings 50 to 60 members of the New Jersey Wilson clan back to the North Carolina plantation for an extremely unusual "family reunion" with the white Wilsons - on the very same plantation where their ancestors' lives were separated by the line of slavery and where racial equality was once unthinkable.