He's a bold, brash billionaire tycoon with an exotic beauty on his arm. Skyscrapers bear his name, and he travels the world in a 727 with beloved family.
For the first time, Donald Trump has flown his wife, Melania, and his five children to Chicago for their first television interview together.
Donald became a family man in 1977 when he married his first wife, Ivana, a former Olympic skier from Czechoslovakia. Together, they had three children: Donald Jr., Ivanka and Eric. Donald and Ivana were married 15 years before their very public breakup in 1992. The following year, he married Marla Maples, and the couple had a daughter named Tiffany. Donald and Marla's marriage ended in 1999.
Then, in 2005, Donald walked down the aisle for a third time with Slovenian model Melania Knauss. In 2006, Melania gave birth to Donald's fifth child, Barron.
Today, Donald's wife Melania and his children—Barron, Tiffany, Ivanka, Eric and Donald Jr.—join him on The Oprah Show stage. Donald Jr.'s wife Vanessa and their children, Kai and Donald III, are here as well.
Although "family man" might not be the first thing that comes to mind when you hear the name Donald Trump, he says that's exactly what he is. "I've always said I've been a great father. Less of a good husband," he jokes. "I love my family."
Donald says his dream is for his family to build on the Trump success. "I'd like them to carry on what I've done," he says. "I've done a good job, and I'd like them to carry on and enjoy another level, and enjoy their lives."
Donald has been married to Melania for six years, and he says this marriage is different than his first two. "I really think that we have a very good friendship," he says. "We've had a very good relationship and a really great friendship."
Marrying Donald meant taking on the famous Trump name, but Melania says she's still the same person she was before saying "I do." "I was always myself," she says. "I know who I am, and no matter what my last name is, I am who I am."
Over the years, Melania says she's developed great respect for her husband. "To be married to my husband, you need to be very smart, quick. You need to be very independent in a way," she says.
Marrying Melania meant blending a new family together, but Donald says it wasn't difficult. "I think Melania made it a lot easier because she's really very smart, and she understands life and she understood what she was coming into. I think she made a concerted effort to get along with the kids," he says. "We were helped by the fact that I never left anyone for Melania. ... When you leave for somebody, it's very hard to blend that family, but I never left [anyone] for Melania. I was a single guy [when] I met Melania. The kids liked her right away."
Ivanka, Donald Jr. and Eric aren't just Donald's children—they're also his employees. All three work for the Trump Organization in New York City.
Growing up, Donald Jr. says it didn't take long before he realized that his father was the Donald Trump. "I got to spend time with my grandfather from Eastern Europe," he says. "I spent a month or six weeks in Czechoslovakia with my grandfather, so I realized very quickly that the life I led in New York, in the United States, wasn't necessarily the norm. I think it was really important because it grounded us."
Although they grew up with many privileges, Eric says the Trump children learned not to take it for granted. "My father is amazing," he says. "He put us in the best schools, but he made us work. There was no free time in the Trump family. We either studied or we worked."
Ivanka says she always knew she and her siblings would one day follow in their father's footsteps. "I think generally speaking, all of us from a young age really wanted to be in the family business and were excited about it," she says.
As children, Donald Jr. says the kids spent a lot of time in Dad's office. "He's a business guy first and foremost, so we spent a lot of time with him, but it was always in a business context," he says. "He'd negotiate a contract, and we'd be playing on the floor listening to this go on. We'd follow him around job sites."
Although we're used to seeing Donald on television shows like The Apprentice and Celebrity Apprentice shouting "You're fired," Ivanka says her father isn't really like that. "He's a phenomenal boss," she says. "There's not a tremendous amount of yelling. With that said, he does not appreciate mediocrity. He expects excellence from everyone that works for him, and that includes his children—so it's a high bar."
Although growing up with a successful father can be a lot of pressure, Donald Jr. says he doesn't always feel the need to prove himself. "I think there's an element of that. That said, there's probably no shortage of confidence in the Trump family," he jokes.
In October 2009, the Trumps welcomed a new member into the family when Ivanka married 28-year-old publishing executive Jared Kushner. The lavish wedding included a 6-foot tall wedding cake and a star-studded, 500-person guest list. "She had a budget—it was unlimited, and she exceeded it," Donald jokes.
Ivanka says each day is better than the last with her husband. "I love being married, and I'm very fortunate to have found the right man," she says.
Ivanka and Jared are ready for the next step in their relationship—in January 2011 Ivanka announced she's pregnant! "The next generation!" she says. Ivanka is about five months along, but she says she doesn't know the sex of the baby just yet.
This will be Donald's third grandchild, but he says he's still not used to being called "grandpa." "It's an unusual word," he says. "I was never in love with that word."
"I love Donald saying it's an unusual word," Oprah says. "It's not!"
Donald is more than a successful businessman—he's also a matchmaker. Donald Jr. and his wife Vanessa have been married five years, and they have Donald to thank.
Vanessa says she was at a fashion show when Donald came up to her. "He said, 'Hi, this is my son, Donald Trump Jr.,'" she says. "It was a little awkward at first, but it ended up being the best setup job."
Although Donald Jr. says he had "zero intentions" of getting married at the time, he couldn't deny that his father picked the right woman. "It wasn't like I asked him to do it, but it ended up working out great because we spent the next six months talking about how awkward that moment was, and she realized I wasn't a total jerk," he jokes.
Donald says when he first saw Vanessa, he knew she was perfect for his son. "She looked so beautiful," he says. "I said, 'Don, that's the person that you should marry.'"
Of all the Trump children, the one most people know the least about is Tiffany, Donald's daughter with his second wife, Marla. Tiffany—named after the iconic jewelry store—has grown up away from the spotlight. She lives quietly with her mother in Los Angeles, but Donald and Marla agreed that it's time for the world to meet her.
Tiffany is passionate about music, but she says her first priority is getting into a good college. "I've always been grounded," she says. "I've always been raised with that sense of morals from my dad and my mother both. It's given me a chance to grow up being Tiffany, not necessarily Tiffany Trump."
Living away from her famous father and siblings has given Tiffany the chance to be a typical teen. "It was great for me getting a chance to grow up as a normal kid just out of the spotlight, versus all of them growing up in New York," she says. "They always had that intense media and spotlight on them."
Donald says one of the things he's most proud of is how Tiffany treats other people. "She really is a terrific student, but more importantly, whenever we get the report card, the teachers write that she is the nicest person," he says. "Every one of them say, 'Tiffany's marks are an A, but more importantly, she's one of the nicest students we've ever had.'"
In 1996, Donald and Melania welcomed their first child together, a son they named Barron. Although he's just shy of 5 years old, Melania says Barron is the boss of the house. "It's school, it's learning, it's lunchtime, it's shower time, it's playtime," she says. "It's a schedule. [He's] kind of a little boss."
Donald, now 64 years old, says fatherhood is different this time around. "As a younger person, you're running through life, and you don't think there will ever be an end to the whole thing," he says. "I think when you get older, and you have some special people around you that are very young, I really believe you appreciate it more."