Behind the Bastards: Part Two - Part One: Is Oprah Winfrey a Bastard?

Release Date: January 16, 2025 | Host/Author: Cool Zone Media and iHeartPodcasts

I. Introduction

In the second part of the Oprah Winfrey series on Behind the Bastards, hosts Jack O'Brien, Bridget Todd, and Andrew T. delve deep into the tumultuous early years of media mogul Oprah Winfrey. Filmed from Las Vegas, Nevada, the episode sets a somber tone as the hosts navigate through Oprah's childhood traumas, family conflicts, and the foundational experiences that shaped her path to fame.

II. Oprah's Early Childhood

The episode opens with Jack O'Brien introducing the focus on Oprah's early life. Oprah's mother, Vernita, took her to Milwaukee, residing in a cramped boarding house owned by Vernita's boyfriend's godmother. Oprah reflects, "I don't know why my mother ever decided she wanted me. I wasn't equipped to take care of me. I was just an extra burden on her" (05:09).

Bridget Todd echoes the sentiment, noting, "I'm just an oblivious kid" (06:11), highlighting the disconnect between Oprah's perception and her family's view of her early life.

III. Family Dynamics and Trauma

A significant portion of the discussion centers around the conflicting accounts of Oprah's experiences growing up. While Oprah recounts severe racial discrimination and feeling undervalued due to her darker complexion, her family members, particularly Aunt Catherine Esters, dispute these claims. Esters states, "If Oprah was discriminated against because of her skin color... she was on the porch because we were very poor" (16:18), suggesting economic hardships rather than racial bias as the reason for Oprah sleeping on the porch.

Jack O'Brien grapples with these conflicting narratives, contemplating whether both perspectives hold fragments of truth: "Nobody has to be lying here. It's just a completely different experience for her and them" (07:56).

IV. Sexual Abuse and Family Skepticism

The hosts delve into the darker aspects of Oprah's childhood, including sexual abuse by a 19-year-old cousin, Trenton. Oprah's accounts of these traumatic events are met with skepticism from her family, leading to strained relationships. Oprah describes her uncle molesting her during a car ride, an event that led to her pregnancy and the subsequent loss of the child. Bridget Todd notes the family's denial: "Even the most supportive family member in her life is doing this to her." (45:30).

Andrew T. adds depth to this discussion, stating, "It's used to sort of marginalize you and say something is wrong with you as opposed to, like, oh, are the adults around you somehow failing you?" (40:18), emphasizing the broader implications of societal and familial responses to trauma.

V. Academic and Social Life

Despite her tumultuous home environment, Oprah excelled academically. She was part of the Upward Bound program, which helped her attend a desegregated, predominantly white school. This transition exposed her to new social dynamics, where she was both celebrated for her academic prowess and ostracized for navigating predominantly white social circles.

Jack O'Brien quotes her father Vernon: "When Oprah was selected to be school vice president, it was a testament to her ability to navigate both black and white communities." (66:00). However, her success also alienated some of her black peers, who dubbed her an "Oreo" for assimilating into white culture. Bridget Todd comments, "Every kid was called something. There's a little bit of, you know, histories written by the winners." (65:31).

VI. Adolescence and Promiscuity

Oprah's adolescence was marked by promiscuous behavior, which the hosts suggest was a coping mechanism in response to her trauma. Her relationships with older boys and men, including her abuser, were misinterpreted by her family as mere promiscuity rather than signs of deeper psychological distress. Jack O'Brien reflects, "This is a reaction to the sexual violence that she experienced from a young age." (38:13).

VII. Moving to Nashville and Later Events

Oprah's return to Nashville brought further complexities. Her mother, Vernita, despite earlier decisions, relinquished custody, allowing Oprah to be raised by her father Vernon and his wife Zelma. This move provided Oprah with a more stable environment but didn't erase the scars from her past. Oprah became increasingly vocal about her experiences, which her family dismissed as attention-seeking behavior.

At 43:25, Bridget Todd muses, "However much you might want to, or one would categorize Oprah as some kind of bastard, there is degrading on the curve element of it, which might just put her at not a bastard." This highlights the nuanced portrayal of Oprah, balancing her philanthropic efforts against the darker elements of her early life.

VIII. Reflections and Conclusions

Throughout the episode, the hosts wrestle with the question of whether Oprah Winfrey deserves the label of a "bastard." They acknowledge her traumatic past and the resilience she demonstrated in overcoming her circumstances. However, they also critique aspects of her character and career choices that may be perceived as toxic or harmful.

Jack O'Brien concludes, "I really do think overall my opinion of her is like, yeah, this is about the best case scenario for someone who gets this rich and famous." (24:18), indicating a complex view that recognizes both Oprah's strengths and flaws.

Notable Quotes:

• "I don't know why my mother ever decided she wanted me. I wasn't equipped to take care of me. I was just an extra burden on her." — Oprah Winfrey (05:09)

• "Nobody has to be lying here. It's just a completely different experience for her and them." — Jack O'Brien (07:56)

• "It's used to sort of marginalize you and say something is wrong with you as opposed to, like, oh, are the adults around you somehow failing you?" — Andrew T. (40:18)

• "When Oprah was selected to be school vice president, it was a testament to her ability to navigate both black and white communities." — Vernon Winfrey (66:00)

• "I really do think overall my opinion of her is like, yeah, this is about the best case scenario for someone who gets this rich and famous." — Jack O'Brien (24:18)

Conclusion

This episode of Behind the Bastards offers a deeply personal and unflinching look into Oprah Winfrey's early life, exploring the intersection of trauma, family dynamics, and the relentless pursuit of success. By presenting multiple perspectives and highlighting the complexity of Oprah's character, the hosts encourage listeners to reconsider preconceived notions about one of the most influential figures in modern media.

Note: All timestamps correspond to the provided transcript and are indicative of where the quotes appear within the episode.