Donald Trump on Letterman, 1986-87

You know , most Friday afternoons we tape a piece for our program on the streets of New York City .

Now , this of course , takes planning , meticulous preparation and a lot of hard work .

So it was only a matter of time before we said to hell with it .

Instead , we decided to wander around aimlessly , pick up a couple of strangers and hang around with them all afternoon and hear boys and girls is what happened .

Hi , how are you ?

Good .

How are you ?

What's your name ?

Right outside their hotel .

We met Neil Brdy and Tanya Anderson just in from Louisville , Kentucky for a weekend vacation .

What are you doing right now ?

Um , we're just getting ready to go out and do a little sightseeing .

And would you mind if we came along with you ?

Would that bother you ?

Because as it turns out we really have nothing to do today .

That's too bad .

Yeah , they planned to spend the afternoon sightseeing and agreed to let us tag along .

I'm guessing it was the jet lag right here .

Taxi .

What Empire State Building and step on it .

Yeah .

Yeah , that's the Lincoln memorial over there .

Yeah .

Right over there .

See the towers .

That's Lincoln and his wife .

Well , that's the Golden Gate Bridge .

You can't see it because of the .

It is beautiful .

You guys are my retinas .

My card is , this is gonna look like something left over for the Patty Hearst kidnapping .

Yes , there's memory .

The I love , here's the card .

This is going to your Peggy and Lyle Peggy and , and it says New York is horrible .

The people are nasty .

The city is dirty and everyone is very mean .

How you doing ?

Good .

How are you ?

I want you to meet some people , some friends of mine .

They're in town from Louisville .

This is Neil and his girlfriend Tanya .

Neil .

Tanya .

Why don't you ?

Come on in Peach Margaritas .

Do you know about current power ?

You just heard of it ?

Is he really ?

He just saved , you know .

Hi .

How are you ?

Are you the security man ?

Yes .

You carrying heat ?

Do you have a gun on you ?

Yes .

Show us your gun here .

I think .

Let me pat you down .

Come on , come on , come on , come on over here .

Let me just see if I can find where your gun is , please .

No .

What is it ?

That's $10,000 .

10 grand .

I don't know .

That might be a little showy with that necklace .

Foxes are what ?

They're clubbed to death .

No , no , no .

Well , they have to be very carefully put to sleep .

Are they're shot in the head ?

Thank you .

Very much for going in .

Thank you .

Oh , my gosh .

Don Dave Letterman .

Nice to see you .

How are you ?

Would you like to come into the office ?

Yeah , let's , let's go into the office because I need to talk to you about the heating in my building .

Don , where , where is Doug flutie ?

For heaven's sakes .

Doug , I have one more question and then we're out of here .

It's the middle of a Friday afternoon .

You didn't know we were coming .

You said come on up .

How busy can you be ?

I have nothing to do .

You know my chi I have nothing to do .

I wish I had more to do .

What would you be doing if you go to Louisville ?

We'll do a couple of real estate deals in Louisville .

There's a spot over here down on the carpet .

Look into that .

Thank you very much .

Bye bye .

All right .

Let's get out of here .

Don't touch anything .

Let's pull , let's keep doing .

That's about it .

And after this , you're pretty much on your own .

Nice meeting .

You take care .

Have a good time .

Bye bye .

Keep your hand on your wallet .

Bye bye .

Got very nice people from Louisville .

We'll be right back with Mr Wizard has enough money to give everyone in the audience tonight a million dollars .

Ok .

Ok .

We'll see what kind of mood he's in .

Uh , ladies and gentlemen , please welcome the author of this book right here , Trump , the Art of the deal .

Donald Trump .

Hi , Donald .

Good to see you .

Nice of you .

Nice of you to stop by .

Thank you , baby .

You know , at the , at the beginning of the show I said you either love him or you hate him .

Now , do you find that that's true or does everybody love you or does everybody hate you ?

Now , most people love me and a few really have great distaste for me .

And why , why , why is it that those people , that few would not care for you because you're so .

No , no , I don't think so .

It's just , I sort of speak my mind a little bit , a little bit like you in that respect .

Yeah , a little bit , like a little bit like me .

Not too much .

How much , how much are you worth right now as you're sitting right here ?

Zero idea .

David .

It depends on what's happening with the world and the market , but the million dollars for each person in the audience sounds like it could be an intriguing idea .

Do you , do you make more money ?

You own casinos ?

How many casinos do you own ?

We have four casinos , four casinos in , at Paradise Island , Atlantic City .

And it's really been very fabulous .

Now , do you make more money from the casinos or more money in real estate development ?

Well , probably real estate in a sense , but real estate is an appreciation business .

Whereas the casinos are cash flow and I don't know , I never really even think of it in those terms .

I tried doing a great job .

I think we have the best hotel casinos in the world and hopefully I have the best real estate in the world with Trump Tower and everything and that's what I like .

All right , let's get back to the assessment of your wealth for a second .

If you had to liquidate .

If you just decided I'm going somewhere else , I'm going to live in a trailer and you wanted to sell off and you wanted to sell off everything .

You'd start with your real estate development , all of your real estate holdings and whatever else you have in your casino and so on and so forth .

You sold everything .

How big would that check be that you put in your pocket when you headed west for the trailer ?

Well , I hate to disappoint but I have zero idea .

David , how come this seat is at such a low level ?

You know , I'm looking at him .

He's got this stage rigged folks .

No , no , but that seat is a good half 66 inches higher than I said .

And so am I Oh , but no , I'm serious .

I think , I think that they're not going to get you off that subject .

No , this is , I think , I think this is the kind of thing that people love to fantasize about because you were unquestionably one of the most successful men in the country .

If not the world and also one of the wealthiest .

So give us a figure that we might ponder here .

You'll never get it out of me , David , you'll never get it out of me .

You'll try , but you'll never get it .

Let's get something like , you know how we're gonna become more successful .

Let's talk about , I read something this afternoon that said in , in the bank right now you have $500 million in cash in cash .

Is that a fair ?

Which paper did you read that ?

Well , I can't divulge those sources .

You have ?

No , no , just tell me .

Is that not true or is that close ?

Am I nuts here ?

Well , I don't know .

I just , you have to tell me where you got that , David .

This is a very unusual interview folks .

Um , you , you won't put a figure .

Just an imaginary figure .

Never would .

Uh , a billion , you're worth a billion dollars , perhaps , perhaps , perhaps , perhaps .

Are we the low side of , perhaps the , um , what were you like as a kid ?

What , what kind of childhood did you have ?

Well , I had a good childhood , wonderful parents , really good parents .

And , and it was a good solid childhood .

I say very normal in a lot of respects , but a very , very solid child , uh , from a standpoint of family .

Are , are you a driven person ?

Are you , do you jump out of bed in the morning and just , I don't think of myself as driven unfortunately , I don't need lots of sleep .

Like some people and some people don't , I don't need that .

I would say that I'm somebody that enjoys what I do and I enjoy it so much that perhaps I do it well , but I really enjoy what I do .

I don't like to think of myself as driven .

I don't like to think of myself really as ambitious .

I just enjoy what I do do is , is what you do something you've always wanted to do .

I know your father was and still is a real estate .

The father was in the real estate business and I've , uh I've been in that and other businesses and different things .

Uh I like what I'm doing .

I just enjoy what I'm doing .

I love the real estate business and I love the other businesses that I'm in .

Could you , could you have done it without your father as a , as a support system ?

Uh , both emotionally and financially .

Did he help you out ?

Was very important .

And I learned a lot from my father more than anything else .

I learned a lot .

My father was out in sort of a tough business in Brooklyn Queens , rent control , property and various properties .

And it wasn't a great business .

It was a good business and he was a solid guy and a bright guy .

And I learned a lot from my father .

And I think if in terms of support , that would be the number one thing that I got from my father .

Have you , have you had failures ?

Big failures ?

Well , I , I , I don't look at failures as failures .

I think a failure is something that you really want to learn by .

I , I would say that I haven't had too many and I wanna keep it that way .

I like .

What's the biggest bath you've taken on a deal ?

I don't know if I can answer it yet .

I mean , let's see what happens so far .

I've been very fortunate , but I mean , we've all been fortunate .

Markets have been going up other than a few weeks .

Did you get hurt in the stock market ?

Not particularly , but I think everybody gets hurt because when you lose a trillion dollars or whatever throughout the world , I suspect everybody's hurt indirectly .

I'm in the real estate business .

You sell apartment , you sell this , you sell that perhaps people don't have as much .

Everybody gets hurt by that .

David , let me ask you one more of these silly questions and I promise after we do the commercial , we'll go on to other topics , then we're going to get serious .

Well , I didn't say that .

What would it take ?

What kind of a hit would it take to get your attention where you would maybe need a drink where somebody came in and said , Don , we got some bad news .

Yeah , that , that's 7-Eleven in Akron .

Well , what up ?

Hopefully David , I wouldn't be in a position where I'd have to take that kind of know that .

I know .

We're just , we're just pretending .

I just want to tell you , you act like you're running for something .

Now , we , we'll do a commercial .

We'll let him think some of these over and try and get it straight out .

Ok , Donald Trump is here .

You're on the cover of the new issue of People magazine .

I don't know what I'm beating around the bush here .

I don't know why you're being so goofy about this .

It says on the cover you're a billionaire .

It does .

So when you says it , I would have to believe it when people , um , what's the deal with you ?

And , and Ed Koch is , is this an old irritation between the two of you or is this something that's really not ?

Ed Koch is a man who I've , I've liked at some points in terms of , I have no objection to Ed , except for one thing , he's not a very capable or competent mayor .

He's done , he's done , he's done a bad as most of you .

New Yorkers will probably know he's done a pretty bad job running New York and that hurts me and it hurts everybody .

And when I see somebody that's not competent and he's running something and something that I have a big , really , a big stake in it bothers me and I do something about it .

Are you speaking from a position of somebody who has a lot of really , really special interest in the city .

No , it's not .

I do have a special interest .

I have a special interest in New York .

New York City is a hot city .

It's a great city .

It's the greatest city in the world according to many and according you're here and we're also here and I hate to see some of the things happening with New York that have happened under the Koch administration .

So I hit him pretty hard in the book , but I hit him fairly in the book .

I hit him very , fairly , probably very hard in the book , but very fairly .

Is it a kind of a pointless defense to say that this city is so big that it is actually unmanageable to a certain extent and he's doing the best , he can sort of just ending it day to day .

I don't think so .

I mean , I hope that's never a defense of anybody .

I did the Wellman skating rink in four months for two million or $2.5 million .

They started seven years before that and were able to build it .

I think they spent something like $15 million .

This is a huge ice skating facility in Central Park , which the city was seven years , seven years , seven years , they could not get it , they could not build it and we did it in four months .

So , you know , you say , hey , it's big and everything else and give them a little bit more time .

But the fact is that's a disgrace .

The zoos are a disgrace , the subways , the schools .

Um , but , but , but , but it's really management , it's management , it's competence , its capability , it's , it's just basic ability and Ed Koch doesn't have it .

Yeah .

But you're speaking again from the over the fence and private enterprise .

He's trying to run a municipal administration .

It can be done .

You think it could be done ?

Absolutely by the right person , it could be done .

Any thoughts .

I mean , would you want to be mayor of the city ?

I did run very well if I was mayor , but I would not want to be the mayor of New York .

Is there something you do want ?

No , I just want to keep doing what I'm doing .

I mean , I'm on your show .

You're a fantastic show .

You're a star in my book .

Everyone's talking about it .

I know that we wrote all about David in the big book .

Now , that's another thing we came up to you that one afternoon completely unannounced .

We were in the lobby of the Trump Tower facility up the road there and we just called up and said , can we come up and see Don ?

And they said , come on now , how busy can you be ?

Uh , but you were a lot of fun , by the way , coming up with a lot of fun and , and I must say , I thought that was very gracious of you to do because obviously you've got a lot better things to do than , than goof around with me .

You're right .

Yeah .

And what about the , are people trying to draft you to run for a president up in New Hampshire ?

Well , I guess a lot of people want to see this country .

It's a shame .

What's happening ?

Japan , Saudi Arabia Kuwait .

They're all , everybody's taking advantage of the United States .

People know that if certain people are running a country that it won't happen .

I mean , when you look at Japan not paying for the defense , we're defending Japan , we're losing billions and billions of dollars .

We're fighting for AIDS help and for farmers and for this and that , and it's a shame and the Japanese folks who I respect greatly but they're not , they're not treating us fairly .

They're really not treating us fairly .

Kuwait , Saudi Arabia , they're not paying us anything for the services we're rendering .

And I think it's a disgrace and I think people look at certain people and maybe me , if , if I were in a position , this country , believe me would not be ripped off like it is and it is just being ripped off so badly by our so allies .

So that's a pretty strong statement .

So now are you saying it's strong ?

I think it's fair and by the way , I have tremendous respect for the Japanese .

I , I do a lot of business with the Japanese and they smile about it too .

They know it .

The country is losing billions and billions of dollars to Japan and we can't afford to lose .

And it's a shame .

But so are you saying this by way of indicating that you could do it better ?

And you do intend to run for president ?

I'm not going to run for president .

But I , I think somebody in eight years , if you came back , would you have a different answer in four years ?

I tend to doubt it .

I really tend to doubt it , but I just think that there are so many ways that this country can straighten itself out and we're not going about those ways , cutting farm aid is not the appropriate thing , cutting help for the homeless and help for the poor and welfare .

Certain things can be done that really will mean big dollars to this country and those things are not being done right now .

Let me ask you one other question .

Um , because I know you have other appointments and stuff to get to if you go to dinner and the bill is like , say $25 how much of a tip would you throw down ?

Yeah .

Oh , you know the way I feel about tips , if somebody does a super job , I give more than anyone .

And if somebody does a lousy job , I probably give less than anybody .

And that's the way I feel about life .

Life should be , you should be rewarded .

For confidence and capability in doing a job and having a smile on your face .

Maybe if that's the case .

And I'm a pretty good tipper when somebody's good .

And I'm a pretty lousy tipper if somebody's not good .

So that's the way it is .

But , you know , sitting here listening to this stuff , it seems to me you are dying to get to some public platform to superimpose those feelings upon the American awareness .

Well , maybe , maybe so , but I'm not , I , I would like to have the feelings known and let somebody else do it and it can be done if it , if it's carried , if the ball is carried correctly , it can be done .

Yeah , but if you want something done right here is the book .

It's Trump , the art of the deal and this is Donald Trump .

Donald , thank you very much for coming for 12 seasons .

Our next guest has broadcast the NFL today with Brent Musburger .

He is a man who knows the angles and the odds on everything from the White House to the Super Bowl .

Folks .

Please say hello to Jimmy the Greek .

Hi , Jimmy , how are you ?

Nice to meet you .

Thank you .

Thanks for being on the show that I can make it ali , but you can come on our show tomorrow then tell us what's wrong with the Giants .

All right , I'll be happy to do that .

Ok .

All right .

Let's I mentioned here the White House to the Super Bowl since we just mentioned it , since we were talking about Gary Hart .

Could you now give us odds on the Republican nominee , the Democratic nominee and the ultimate one , Gary Hart ?

Too , too much love has done for you .

What's that blows out your brain ?

Ok .

That's mine .

I see .

Ok .

Now , the Republican nominee , it's 8 to 5 .

That Bush beats door .

Now it's 6 to 1 .

You can't guess who the Democrats are going to be .

And I don't care who you take and it's 50 to 1 against Hart .

And are there , are there odds now on Cuomo being , uh , brought back into the fray ?

Well , if anybody would make them , it would be me and I don't think Cuomo wants to run , but I would have to make him a 20 to 1 shot only because he doesn't want to run .

If he would run .

He'd be a 3 to 1 shot .

If Aya Coca would run , he'd be 2 to 1 .

You know ?

Is that right ?

You think so ?

What about a guy like Donald Trump who looks like a candidate somewhere down the road ?

But won't , won't really say , you know , I'm glad you asked that .

But you see , there's a difference here .

There's a way of doing this .

Donald is a Republican sort of in the middle of the road .

He'd have to leave that side because Bush and do have that all tied up .

I'm talking about the delegates but if he would leave and go on the Democratic side , he could bury all these people .

Look at Hart .

I mean , all of a sudden he's number one .

I mean , that's an impossibility .

Now , Donald is Mr Trump is arrogant .

He's egotistical but , but he's smart and he's beautiful and he knows how to do things .

If he would switch to the democratic side , he could win the Democratic nomination because he knows how to put things together , put slates together in every state he could win because then he'd go against Bush and I'll tell you something , it would be a close election .

I know that sounds ridiculous .

Ridiculous because I think , I think when people , no , no , I mean , from the same point when you talk to Donald Trump , you think maybe in four years or in eight years .

But now to suddenly , uh , everybody there , David , but things have already started and for him to announce that he's switching parties .

I mean , who's going to accept that ?

And Reagan did not ?

All right .

Um , now how do we describe you ?

You're a professional gambler and I was a professional .

You don't gamble anymore ?

No .

Oh , except on the market every morning .

I get five or 600 shares of stock every day .

But most of your life you were , that's how you made 1962 .

I think you were the , the first gambler that Americans probably became aware of on a , on a national bet because I made the numbers first .

That was all , you know , I mean , I've been around for 50 years .

So , consequently , do you remember how you started gambling ?

What your first bet was the first big one ?

I remember the first time I bet $500 or more was on Lewis against smelling 1930 something , 39 or something .

I had to borrow $500 so I could lay 9 to 5 .

Had , had this been something you , you got from your family or your friends ?

Were they all gamblers as well ?

No , I was born in Steubenville .

I was born in Steubenville , Ohio .

I mean , and I was 25 before I found out that gambling was illegal because they had to live in gambling houses in a town of 40,000 .

We , you know , I say that , I mean , it's kind of cute but it's true if you had to exist , you either had to work in a coal mine or a steel mill or gamble .

And I thought that was easier when you were , when you were gambling regularly on any given weekend .

How many different bets at ?

How much money would you have out ?

No , no , you don't .

When I was gambling , I never played a lot of games .

I would wait and play a lot of money on one game .

Give us an example .

The big one that I lost in fact was Kentucky against Santa Clara in 1950 .

And I bet a quarter of a million on it .

But , you know , I'm sorry , a quarter of a million on one game .

Yeah .

But I lost it .

But , you know , I bet 50,000 on the other five bowl games that day and I won all five of them .

But you know what my wallet to give you a hand and , and , and you just , you , yeah , I broke even , but the whole thing about it , you know , today there's people in Vegas and around the country that do that every week .

I mean , it was , it's really mushroomed .

Hasn't hit your head .

Uh , do you , do you remember your single biggest win ?

And your single biggest loss was that at the quarter of a million ?

No big win was Truman against Dewey .

You know , really ?

You had money on that .

I didn't have to put up too much for that .

I wouldn't think so .

And how much did you end up bringing home ?

I took 17 to 1 .

I mean , it's a matter of record that I won 100 and 70,000 but Truman , but , uh , was around and somebody , you know , by the time the story was told and re he had me winning a million , 700,000 and I had the IRS on my back for about seven years after that .

How , uh , how are you and Brent getting along wasn't there ?

About five years ago ?

You guys got into a scuffle in a bar or something ?

No .

Listen , we've been together for almost 13 years .

We're entitled to one argument .

I mean , I , you , you have that many arguments with your wife every week .

Brent said something he shouldn't have said and I did something I shouldn't have done .

He and I are the closest of friends .

I sign on your show .

But somebody , somebody did get punched .

Right .

Well , it was about even a little punch out .

Did you hear that ball ?

We're entitled to one punch out .

Uh , this is , uh , this is the man you see every , I guess Saturday and Sunday now , right ?

Saturday and Sunday this week , right ?

And next week also , Jimmy , the great pleasure to meet you , Jimmy .

Thank you very much for joining us .