Donald Trump’s Fascination with Deborah Messing and ‘The Apprentice’: Revelations from a New Tell-All Book

In the world of reality television and politics, few figures loom as large as Donald Trump. From his days as the host of “The Apprentice” to his tenure as the 45th President of the United States, Trump has always been a lightning rod for controversy and fascination. A new tell-all book, “Apprentice in Wonderland,” by Rin Studa, promises to shed light on lesser-known aspects of Trump’s life and career, particularly his longstanding infatuation with actress Deborah Messing and his enduring obsession with his reality TV show.

The Celebrity Crush: Deborah Messing

Deborah Messing, best known for her role in the hit sitcom “Will & Grace,” has found herself at the center of Trump’s admiration, according to Studa’s book. Trump’s apparent crush on Messing dates back to the early 2000s when “The Apprentice” and “Will & Grace” aired back-to-back on NBC. Trump is quoted in the book reminiscing about an encounter with Messing: “She came up to me with her beautiful red hair and she said, ‘Sir, I love you. Thank God for you. You’re saving the network and you’re saving my show.’”

However, Messing’s subsequent criticism of Trump during his presidency has reportedly been a source of lingering irritation for him. As a vocal opponent of Trump’s policies and actions, Messing didn’t shy away from expressing her disapproval. In 2017, an entire episode of “Will & Grace” was devoted to mocking Trump, including comparisons of his skin color to Cheetos, which only deepened the former president’s sense of betrayal. “He is very, very upset that Deborah Messing criticized him as President of the United States,” Studa writes, suggesting that Trump felt Messing owed him loyalty due to their shared network history.

Trump’s Obsession with “The Apprentice”

“The Apprentice” remains a significant touchstone for Trump, influencing his approach to politics and his public persona. Despite the demands of his political career, Trump has never fully detached from the show that catapulted him to new levels of fame. Studa reveals that Trump continues to draw parallels between his reality TV experience and his political decisions, particularly when selecting his running mates.

Cynthia Cuda, co-editor-in-chief of Variety magazine, interviewed Trump six times after his presidency and noted his ongoing preoccupation with “The Apprentice.” According to Cuda, Trump views the selection of a vice-presidential candidate through the lens of casting a reality TV show, seeking someone who will not overshadow him but will complement his image. For instance, Ohio Senator JD Vance is likened to Bill Rancic, the winner of the first season of “The Apprentice,” due to his unwavering support and positive portrayal of Trump.

Conversely, Vivek Ramaswamy, who has shown more flamboyant tendencies, is compared to Sam Solvie, a contestant known for his outrageous antics, such as trying to sell lemonade on Wall Street for $1,000 a glass. “Vivek Ramaswamy is too out there,” Cuda notes, implying that Trump prefers a running mate who will not divert attention away from himself.

Behind the Scenes: Trump and Family Moments

The book also delves into personal moments from Trump’s life, including a touching scene from “The Apprentice” involving his family. In a classic episode from 2006, a 35-year-old Melania Trump is seen holding baby Barron as Donald Trump pulls up in a convertible Rolls-Royce, symbolizing the blend of his personal and professional worlds.

The Response

Unsurprisingly, the book has elicited strong reactions from Trump and his supporters. A spokesperson for the Trump campaign dismissed Studa’s claims, accusing the author of suffering from “Trump derangement syndrome” and allowing it to “rot his brain.” Despite the dismissal, the book offers a captivating glimpse into Trump’s psyche and the lasting impact of his reality TV days on his political life.

Conclusion

“Apprentice in Wonderland” provides a revealing look into the multifaceted world of Donald Trump, exploring his personal obsessions and the intertwining of his television persona with his political career. From his unrequited admiration for Deborah Messing to his strategic approach to political alliances, the book paints a complex picture of a man who remains a dominant force in American culture and politics. As Trump continues to navigate the post-presidential landscape, these insights offer a deeper understanding of the motivations and influences that shape his actions and decisions.