September 23, 2004

Stern and Trump discuss their mutual disdain for the Iraq War and George W. Bush, The Apprentice, Mark Cuban, prenuptial agreements, his relationship with Melania, his daughter’s love life, and New England Patriots’ player Tom Brady.

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00:47 Trump and Stern discuss their mutual dismay over the state of the war in Iraq.
01:04 Trump on the war in Iraq: "The war is a total disaster. It seems to me to be almost worse than Vietnam"
01:42 Trump talks about how unfairly John Kerry was treated during the 2004 Presidential campaign - the "Swift Boat Veterans for Truth"
02:43 Trump: "You'd have to be pretty hard-line to now still support the Vietnam war"
02:52 Trump discusses his agreements and disagreements with Bush - "I love his tax policy and I hate his war." Trump also strongly disagrees with the Bush ban on embryonic stem cell research.
03:37 Trump says "It's a funny thing - the Republicans are known for business and yet the economy always seems to be tanked with the Republicans." He also brags that Bill Clinton is a member of his golf club and calls the former president "a really good guy."
03:49 Discussion of interest rates
04:24 Trump: "I think Bloomberg is doing a very good job"
04:52 Discussion of the "hotness" of Mayor Bloomberg's wife
05:15 Stern discusses how Melania was able to keep Trump for so many years, and their marriage plans
05:54 Trump discusses the importance and difficulty prenuptial agreements.
08:05 Trump says that his father asked his mother for a prenup before they married, but that she refused to sign one.
10:53 Stern brings up speculation that Trump purposely divorced Marla Maples before the prenup expired. Trump doesn't confirm this explicitly, but speaks speculatively about doing it for that reason.
12:47 Trump tells his oft-repeated story about watching Howard make jokes about him on TV from his honeymoon suite with Marla Maples.
13:48 "OJ was perhaps the most guilty human being I've ever seen" - Discussion of OJ Simpson, who Trump feels is guilty.
15:04 Trump discusses his encounter with Nicole Brown Simpson in a restaurant while he was at dinner with OJ Simpson. He claims that she was rude and purposely embarrassed OJ in front of people.
16:09 Trump discusses the allegations that OJ Simpson beat his wife routinely before she was murdered. He also compares the Simpson marriage (unfavorably) to that between his parents.
16:28 Stern returns the discussion to Trump's relationship with Melania. Trump talks about his history of womanizing and says that he believes in the importance of "the woman behind the man."
18:45 Trump on his relationship with Melania: "It's everything. It's sexual, it's the friendship"
19:17 Discussion of Melania's body, her lack of cellulite, and how she was unfairly treated as a "dummy" by the press.
19:58 Discussion of Australian model Kylie Bax.
20:15 Trump says that he doesn't like anal sex
12:44 Discussion of his show, the Apprentice.
21:56 Trump goes into detail about his negotiations with NBC for payment for The Apprentice. He is vague about he exact number, but claims that it is more than $1 million but that he "didn't even get close" to the $24 million/episode that he initially asked for.
24:48 Discussion of Mark Cuban and his show, Benefactor, which was similar to The Apprentice. Cuban in a tabloid claimed that Trump lied about his wealth and business acumen.
26:16 Trump briefly mentions Trump University and Trump Magazine
27:40 Trump discusses his casino business
28:12 Trump talks about his net worth
28:26 Robin brings up Trump's casino bankruptcies. Trump downplays their importance to his net worth, saying that they are "less than 1 percent"
29:58 A man that Stern claims is a "vice president at NBC" disputes Trump's claims about The Apprentice's TV ratings.
32:05 Trump discusses how his children feel about him and Melania potentially having children and cutting into the inheritance available to them.
32:39 Stern calls Ivanka Trump "a piece of ass," and Trump says "your are the last person I would introduce her to"
33:12 Discussion of Ivanka Trump's love life. Stern asks Trump if she's dating "a white guy". Trump talks about the "aristocrat" that she is dating (presumably Bingo Gubelmann).
33:54 Trump is disappointed that Ivanka didn't want to date a football player (later revealed to be Tom Brady), expresses concept that she's "becoming a blue blood," and says "I think my daughter looks down on me."
34:44 Discussion of Trump's will and testament
34:58 Trump discusses George W. Bush's estate tax plan
35:47 They return to discussing The Apprentice and take a call from Dominic
39:14 Stern and Trump discussion his upcoming wedding.
39:35 Stern and Trump again discuss the murder of OJ Simpson's wife, which happened very soon after Trump's wedding to Marla Maples. Trump concedes that Simpson is a bigger "reality star" than he is.
40:06 A caller says that the "football player" that Trump wanted to set up with his daughter was Tom Brady of the New England Patriots. Trump says he "doesn't admit to it" but also doesn't really dispute it, and calls Brady "terrific, terrific."
40:35 Trump mostly refuses to answer Stern's questions about whether he would allow Ivanka to date a black man, but says "my daughter is very open minded, I would say that"
41:07 On the phone, Dominic and Trump talk more about prenuptial agreements.