February 27, 2006

Trump brings two of his children, Ivanka and Donald Jr., onto the show to promote the fifth season of The Apprentice.

There is an extended discussion of Trump’s feud with Martha Stewart over her failed spinoff of The Apprentice.  Trump says that he felt attacked by her. Howard and Robin suggest that he has a tendency to “counterpunch” in a disproportionate way and Donald Jr agrees.

Trump’s children also discuss their roles in the Trump business, their love lives, and more.


Trump comes across as extremely thin-skinned in a way that is similar to his behavior as president. Howard and Robin’s analysis of his personality could be applied directly to any number of similar incidents since being elected. Don Jr’s description of Trump’s tendency to hold grudges is also very interesting.

Tags: Barron Trump, Bingo Gubelmann, Donald Trump Jr., Ivanka Trump, Martha Stewart, The Apprentice, Tiffany Trump, Wharton School of Business
Duration: 31:00

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0:49 Discussion of Trump's "feud" with Martha Stewart, who he blamed for the failure of an Apprentice spinoff
7:03 Stern asks Trump if he has ever forgiven anyone, and Trump replies with "rarely"
7:12 Donald Trump Jr talks about his father's tendency to hold grudges
7:36 Fascinating conversation with Trump's children about whether it is hard to be related to him, and what it's like to work for him
9:07 Trump jokes about cutting his children out of his will if they don't treat him with respect
9:36 Stern asks Ivanka and Donald Jr if they've ever discussed their father's will
11:00 Ivanka talks about the difficulties they faced when Tiffany Trump was born
12:20 Ivanka on how hard she and Donald Jr work for her father
12:55 Stern asks Ivanka about how she got into the Wharton School of Business
13:33 The Trump children talk about their high SAT scores
14:20 Stern stumps the Trump children with the question, "What's 17 x 6?"
15:28 The conversation returns to Martha Stewart. Robin feels that Trump's attack on Stewart's daughter was cruel.
18:18 Stern discusses how attractive he find Ivanka. "Your father says you're one of the most attractive women on the planet"
18:43 Stern regular Artie Lange jokes about dating Ivanka
19:28 Stern jokes that he felt out of place at Mar-a-Lago because he looks Jewish
20:20 Ivanka explains that her dating life is complicated by her famous father
21:26 Ivanka discusses her relationship with long-time friend Bingo Gubelmann
22:28 Ivanka jokingly claims to be a virgin, and says that she does not discuss sex with her father
22:46 Robin calls Trump a "sexual predator"
23:16 The Trump children describe their roles in the family business
24:14 Stern asks the children about their relationship with their method, Ivana
26:11 Gary asks about Trump gave his son as a wedding gift
26:39 Stern again asks about Ivanka's dating life and her relationship with other famous rich children, like Paris Hilton.
27:14 Stern asks Ivanka if she would ever date a black man. Her father insists that she would, but she says that she never has.
28:21 Stern asks Ivanka how many dates she needs to have before she will sleep with someone, but she refuses to answer
29:32 Ivanka says that she would never date a woman and would never kiss a woman
30:04 Trump discusses a Dubai business project involving port security. Stern says that he is uncomfortable with a Dubai-based company filling that role.

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