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The First Son: The Life of Donald Trump Jr. Aired 9:30-10p ET

Aired July 14, 2017 - 21:30   ET




[21:31:49] RANDI KAYE, CNN CORRESPONDENT: Donald Trump Jr., family man, business man, and his father's Defender in Chief. Tonight, a close up look at the president's oldest child, the one who has landed in the middle of a major controversy over a meeting in Trump Tower with a Russian lawyer during the campaign.

I'm Randi Kaye. And this is a CNN Special Report, "The First Son, the life of Donald Trump Jr."

(voice-over) Donald J Trump Jr., born to Donald and Ivana Trump on the last day of 1977, heir to a legacy, still being built, destined to loom large over Manhattan.

MICHAEL D'ANTONIO, AUTHOR, "THE TRUTH ABOUT TRUMP": I think one has to have some compassion for someone who is trust into this role of almost a prince of New York City.

KAYE (voice-over): Donald Trump Jr. grew as the empire grew around him. A toddler when his father made his name as a big Manhattan developer, revitalizing an old abandoned hotel, in grade school when ground was broken for Trump Tower.

DONALD TRUMP JR., PRESIDENT TRUMP'S SON: I remember playing with trucks on the floor of his office. You know, going trick-or-treating in his office.

KAYE (voice-over): To see dad, Don Jr. and eventually his siblings would need to visit him in the office.

TRUMP JR.: I think throughout our lives. He's always been there. It's usually on his terms. It wasn't a typical let's go play catch in the backyard, sort of father-son relationship.

KAYE (voice-over): And a typical relationship, that worked until the early 1990s when Donald and Ivana Trump divorced. The world read all about it.

TRUMP JR: I was 12. So it was a difficult time. I mean, certainly difficult reading about it in the papers every day on the way to school.

KAYE (voice-over): Don Jr. read about it, because Trump Sr. was talking about it.

D'ANTONIO: He said things that no man should ever say about his wife. In private, let alone in public. And I think it really affected Don Jr. And he went through a long period of time when there was real chasm between father and son.

KAYE (voice-over): They didn't talk for a year.

D'ANTONIO: I think Don Jr. identified very much with what his mother was going through with the pain that she felt. And I think he was quite angry.

KAYE (voice-over): Anger that died down as he grew up and headed to boarding school in Pennsylvania.

D'ANTONIO: He was sent off to a boy school in Central Pennsylvania, at the time when this happened. And he talks about that being kind of a saving grace in his life that he says this was an all-boy kind of place where he could play with the other kids. And, not necessarily be a Trump.

KAYE (voice-over): His mother's father Milos Zelnicek helped too.

TRUMP JR.: Spent a lot of time with our maternal grandparents. They were from communist Czechoslovakia.

KAYE (voice-over): He would visit them for several weeks every summer.

D'ANTONIO: His grandfather on his mother's side, I think was probably the key male role model for Donald Jr. growing up.

KAYE (voice-over): Outside Prague Zelnicek taught him how to fish and hunt.

TRUMP JR.: You can pull the trigger twice you will get two shots out of it.

[21:35:02] KAYE (voice-over): During the presidential campaign, Donald Trump Jr. and his brother Eric showed off their hunting skills to CNN's Jake Tapper.

TRUMP JR.: We got into it very young age. We had a grandfather, who is a blue-collar guy, electrician from communist Czechoslovakia.

KAYE (voice-over): Love of the outdoors came from his maternal grandfather. From his paternal grandfather Fred Trump, he learned about work.

TRUMP JR: I remember as a kid we go spend the weekend with them and it was, wow, what do you want to do? It was, I don't know, I'll do anything you want. Well, I guess, we go collect a rent.

KAYE (voice-over): Collect rent from tenants who leased Fred Trump's apartments in Brooklyn, in Queens.

TRUMP JR.: He didn't understand how to relate to a child in a way. It was just a worker. And hat's what he did.

KAYE (voice-over): In beginning in his early teens it's what Don Jr. did too. He was the son of a billionaire. He didn't need to work. But his father made him.

TRUMP JR.: He always wanted to make sure we understood the value of a dollar. My first job was as his dock attendant.

KAYE (voice-over): At one of his father's properties in Atlantic City, New Jersey.

TRUMP JR.: Out on docks. It was nice. And I had to work. But you were hooking up boats. And you're sort of running around. It was a lot of fun, making minimum wage and tips.

KAYE (voice-over): The work soon got tougher.

TRUMP JR.: Going into some landscaping. Utilizing heavy equipment and I'm 15 years old. So wait a minute, I'm older, I'm working much harder. There's no longer a tip component. And so I remember going to him about halfway through the summer being like this, I'm working so much harder. How come I'm still making minimum wage and I don't even have the tip component. I'm actually making less, he's like, you didn't ask, why would I pay you more than you're willing to work for?

KAYE (voice-over): Ask for what you need. An early lesson, Donald Trump Sr. taught his eldest, another.

TRUMP JR.: Don't trust anyone.

KAYE (voice-over): It was something Don Jr. says his father began telling him early on.

TRUMP JR.: Don't even trust me. And one day, he was like said, do you trust me? And I remember saying, yes, of course, you're my daddy, and he just looked at me very disappointed as though I hadn't learned this lesson as a 7-year-old kid.

KAYE (voice-over): Other lessons.

DONALD TRUMP, (R) PRESIDENT OF THE UNITED STATES: When my children were growing up bigger, when they didn't even know what drinking was, I'd say, no alcohol, no cigarettes, no drugs.

IVANKA TRUMP, PRESIDENT TRUMP'S DAUGHTER: Every day of our life. Every morning, don't drink, don't do the drugs.


UNIDENTIFIED MALE: Every morning, before school without fail.

KAYE (voice-over): A lecture Trump Sr. gave regularly, in part, because his brother Fred drank too much and died young.

TRUMP SR.: He got hooked on alcohol, just hooked. And ultimately, it just was devastating. KAYE (voice-over): A lesson Don Jr. didn't take with him when he followed his dad's footsteps into the Wharton Business School at the University of Pennsylvania.

D'ANTONIO: He was a bit of a wild child. I mean, there are stories of Donald Trump, the elder, showing up to see his son during his college years, and then having some real conflicts that were heard by everyone in the hallway of the dormitory. So this --

KAYE (on camera): Over what?

D'ANTONIO: Oh, I think it was over whether this young man was pulling himself together.

KAYE (on camera): Did that cause a problem in their relationship?

D'ANTONIO: Oh, I think, Don Jr. is drinking and carousing definitely offended his father.

KAYE (voice-over): After college, despite the degree in business, Don Jr. didn't head for dad's empire, but away from it. Aspen, Colorado, where he fished, and hunted, skied, tended bar, and drank.

D'ANTONIO: I'm not sure that it was clear that he was going to ever fall in line.

KAYE (voice-over): He returned home in 2001, following an arrest for public drunkenness during Mardi Gras in New Orleans, where he spent 11 hours in jail.

Back home, he joined the family business. Something he said was a choice. Something he always wanted to do. Trump biographer, Michael D'Antonio isn't so sure.

(on camera) Would you say that Donald Trump Jr. chose his own path or was he raised to take over the family business?

D'ANTONIO: You know, I don't think any of the Trump children really chose their own path in life. If any one of them had said, I'm out of this, they would have found themselves really isolated and perhaps almost banished from the family structure. This business and the family are one in the same.

KAYE (voice-over): Back on the path, Don Jr. began to employ the lessons he learned on the floor of his father's office. Work hard. Work often.

TRUMP JR.: I used to love getting the call at like 5:00 in the morning on a Saturday, being like why aren't you in the office? I feel like, I am in the office. He's like, no you're not, because I am.

KAYE (voice-over): By 2005, he was showing off Trump's newest building and his soon to be wife.

TRUMP JR.: My fiancee, the very lucky, Vanessa Hayden. KAYE (voice-over): Vanessa Hayden, a former Wilhelmina Model became Vanessa Trump in 2005. Soon after, they became parents, five children in seven years.

[21:40:02] TRUMP JR.: What are you doing? What are you doing? Yeah, buddy, first time without a vest. Good job.

I got you.


TRUMP JR.: I love you.

KAYE (voice-over): And as the kids grew, so did Don Jr.'s involvement in his father's empire. Joining the apprentice.

TRUMP SR.: Don, tell them what you are looking for?

TRUMP JR.: You'll be judged on three criteria.

KAYE (voice-over): Promoting it.

TRUMP JR.: It's plenty of company that would kill for the kind of free press that we get. You know it's really a great tool.

KAYE (voice-over): And moving into a corner office as an executive vice president. When he could, he go to upstate New York where he'd fish.

D'ANTONIO: He would withhold his last name from people. And, may know he's a good fly fisherman. But they don't know that his last name is Trump. And I can relate to that. I think most of us could. We wanting some refuge from all of the attention that Trump's received.

KAYE (voice-over): Ahead, how that last name would catapult him into on to the campaign trail and into controversy.

TRUMP JR.: It take's a unique character to want to be able to do this. To go up against, I think it's fair to say, the most corrupt candidate in the history of the presidency.


[21:45:15] TRUMP JR.: I'm 38 years old. I may not quite be a millennial but I'm not that old. Yes. But I am the father of five young kids. And I want to make sure that the America will live them is better that the one I got. And that's not happening right now.

KAYE (voice-over): Donald Trump Jr. stumping for his dad and echoing his father's promise to make America great again.

TRUMP JR.: As I've traveled across the country for these last few weeks now, now that I've been a politician for 12, maybe 13 days. It's incredible to see the outpouring, the warmth, and we are just excited. I mean, I really love what my father is doing here. He really loves this country.

KAYE (voice-over): During the campaign, Don Jr. was one of his father's greatest champions.

D'ANTONIO: He wants to go through this brutal process to back -- to be able to give back. I mean he's truly, you know, it's incredibly selfless. And it's amazing to see.

KAYE (voice-over): Also one of his greatest defenders on Russia.

TRUMP JR.: I can't thing of bigger lies. But that exactly goes to show you what the DNC and what the Clinton camp will do. They will lie and do anything to win.

KAYE (voice-over): And more, at times playing attack dog.

TRUMP JR.: It takes a unique character to want to be able to do this, to want to take this on, to go up against, I think it's fair to say, the most corrupt candidate in the history of the presidency.

KAYE (voice-over): Along with his sister Ivanka and brother Eric, Don Jr. had a tremendous influence on his father during the campaign. From helping convince him to fire his first campaign manager, Cory Lewandowski.

TRUMP JR.: Were we involved in talking about this with him, sure.

KAYE (voice-over): To persuading his dad to choose Mike Pence as a running mate.

(on camera): How much influence would you say Donald Trump Jr. had over his father during the campaign?

D'ANTONIO: I think Donald Jr. communicated with his father what a lot of Middle America, what those people were feeling. And his instincts were right.

KAYE (on camera): Would you say Don Jr. helped his father or hurt his father on the campaign trail?

D'ANTONIO: Oh, I think during the election campaign Donald Trump Jr. helped his father far more than he hurt him. I think there was a constituency that would not have been receptive to Donald Trump but for his son's efforts to make that connection. He came across as a real sportsman who understood what guys who hunt and fish are interested in. And, reassured them that his father was a OK.

TRUMP JR.: I'm a big outdoors man. I'm a big hunter. Unfortunately I'm wearing a suit and not carhartts or camo. I would much rather be in a tree stand right now in Iowa.

I'm looking at all saddles up there. Saying I should put up a tree stand and be hunting right now. But, I'm hunting something else until November.

KAYE (voice-over): But like his dad, Don Jr. courted controversy. He compared Syrian refugees to skittles. He wrote on Twitter, "If I had a bowl of skittles and I told you just three would kill you. Would you take a handful? That is our Syrian refugee problem." Backlash online was fierce.

President Obama's former speech writer, John Favro, weighing in with this picture of a bloodied Syrian child in Aleppo writing, hey, Donald J. Trump Jr., this is one of the millions of children you compared to a poison skittle today.

TRUMP JR.: I don't want it to be a distraction. But you know to me, it was a simple metaphor. I guess I'm a straightforward guy.

KAYE (voice-over): Straightforward? Perhaps, but it got him into trouble again, when he said this.

TRUMP JR.: Without the media this wouldn't even be a contest. But the media has built her up. They've let her slide on every indiscrepancy on every lie, on every DNC game trying to get Bernie sanders out of this thing. If Republicans were doing that they would be warming up the gas chamber right now.

KAYE (voice-over): The anti-defamation league which works to end anti-Semitism urged Don Jr. to stop making holocaust jokes and retract his statement.

TRUMP JR.: I didn't say anything about the holocaust. I was talking about media bias. I was talking if you are conservative it's essentially capital punishment.

KAYE (voice-over): Under the glare of the campaign spotlight, he continued to stumble. Playing off Hillary Clinton's basket of deplorable comment, Don Jr. posted on Instagram, this movie poster from "The Expendables" re-titled, The Deplorables.

But look closer, over his father's shoulder, is Pepe the frog, a popular symbol among white supremacists. A spokeswoman for then candidate Trump tried to clean up the mess, "Don Jr., like Mr. Trump, disavows any groups or symbols associated with a message of hate."

[21:50:03] D'ANTONIO: Donald Trump Jr. learned to be provocative at the foot of the master. There's no person more provocative than his dad. And I think it can become almost thrilling to be the guy who says outrageous things. And for Donald Jr., I think this was thrilling but it was also perilous.

KAYE (voice-over): It seems the more the younger Trump opened his mouth the more he opened himself up to criticism. An avid hunter and national rifle association member, Don Jr. found him self defending a big game hunt when this photos made the rounds on social media.

Don Jr. and his brother Eric proudly posing with trophy kills from a 2012 Zimbabwe hunt, a leopard, a water buffalo, a massive crocodile hanging from a noose in a tree. And this, Don Jr. holding the tail of an elephant in one hand a large knife in the other.

Animal activists sounded the alarm. But the younger Trump pushed back saying villagers were grateful for the meat.

TRUMP JR.: I've always been a hunter. You know, something that I've done for a long time. It's tough to talk about something like it. Come on, I get it. You know the reality of the situation is, you know, there's a lot of things that are tough to talk about.

Once you get exposed to it, you realize it's not -- it's not just like this savage thing that, you know, people try to make it.

KAYE (voice-over): Don Jr.'s love of hunting so strong, he once even joked, that he might run the Department of Interior one day.

TRUMP JR.: So, I don't know if I might be the head of it or just informing them. But, you know, rest assured for all the hunters and shooters out there they would know, you know, I would have his ear.

KAYE (voice-over): At the Republican National Convention just months before his father would win the White House.

TRUMP JR.: Good evening. I'm Donald Trump Jr.

KAYE (voice-over): Don Jr. made his most public push to convince voters his father was the only choice.

TRUMP JR.: A president who will unleash the greatness in our nation and in all of us, who will give the hard working men and women, who built this great country, a voice once again.

That president can only be my mentor, my best friend, my father, Donald Trump.

And when we elect him, we'll have done all that. We'll have made America great again, greater than ever before.

KAYE (voice-over): The speech played well. But it was quickly overshadowed by questions of conflict of interest.

After his father's historic victory, Trump's team defending Don Jr.'s role on the Transition Executive Committee vetting candidates for cabinet positions. Transition members argued none of it blurred the lines between Trump's business and the government.

JASON MILLER, TRUMP TRANSITION SPOKESMAN: The transition team has been very transparent. And the fact that Donald Trump Jr. is on the transition team, that he is someone who is helping us form this government.

KAYE (voice-over): Coming up, the first son trades the campaign trail for the corner office, stepping into his father's shoes.

KELLYANE CONWAY, COUNSELOR TO THE PRESIDENT: He has agreed to step away from everything that has to do with the Trump organization. He is turning over management of his wildly successful business to his two sons.

(COMMERCIAL BREAK) [21:57:20] KAYE (voice-over): The election of Donald Trump Sr. to president of the United States meant another thing for Donald Trump Jr. Stepping into his father's outsized role at his own company and fully assuming the life he once ran from.

TRUMP SR.: My two sons who are right here, Don and Eric are going to be running the company. They're going to be running it in a very professional manner.

KAYE (voice-over): Since his father took office, Donald Jr. took the helm of the Trump organization, globetrotting to continue to grow the company's real estate and licensing empire, Dubai for a golf course opening.

TRUMP JR.: See the incredible vision that Sheikh Mohammed has been able to put forward in this country is truly awe-inspiring.

KAYE (voice-over): Vancouver for a new Trump hotel.

All while operating in the bubble of secret service protection as the first son. And all while the absence of Donald Sr. the businessman looms large.

TRUMP JR.: What is it like to doing all this without your dad?

He was such a great sounding board. Did not having that to go to is definitely something you miss.

KAYE (voice-over): Something else Donald Jr. apparently misses about his father?

TRUMP SR.: Say hello to Don Jr.

KAYE (voice-over): The raucous campaign that he rode to a stunning victory.

TRUMP JR.: I thought I would be going back to my regular job. I thought I would be really exited about that. But, you know, once you got a little bit of taste of that action it's hard to leave.

`You know, I guess -- listen, deals are still exciting. But when you're sort of guy out there every day, 24/7, fighting in this thing it's like a great fight, the intensity.

KAYE (voice-over): Despite sitting atop the Trump business empire, Donald Jr.'s attention for politics has many Trump watchers wondering if that is where his true faith lies.

KAYE: What do you think the future holds for Donald Trump Jr.?

D'ANTONIO: You know, up until the middle of 2017, I would have said that Donald Trump Jr. is destined for a life in politics. I would have imagined him to hold a high office, maybe, United States senator, maybe governor.

But I think what he is seeing in his father's first six months and in the campaign, may have sobered him up. You know this is not an easy role for anyone. And, he has witnessed his father struggle to get some traction in Washington.

So, my idea now is that 10, or 20, or 30 years from now he'll be Donald Trump businessman. He'll have an office in Trump Tower. And he'll preserve the family legacy.