What did you think of Donald Trump a decade ago?

I didn’t read the whole thread.

But I remember him being a punchline for jokes as far back as the late 80’s. And nothing since then has changed.

I worked for SPY long ago and helped factcheck an article showing Trump was, in fact, bankrupt. This was in 1990 or 1991. His continuing existence outside jail or a cardboard box was infuriating but easy to understand–owe the bank $100 and the bank owns you, owe the bank $1 billion and…

After that I always thought of him as a fraud; I was surprised by the success of “The Apprentice” but paid it no particular attention, because there’s tons of successful bullshit on TV. And here we are.

I actually found DJT pretty amusing back in the day. He was a frequent guest on the Howard Stern show, which I listened to on my way to work & he came across as candid, honest, shallow, intelligent, and funny. I later watched him on The Apprentice & appreciated his politically incorrect style, which was a breath of fresh air at that time. Never in a million years expected that he’d ever be President of the United States though…

He used to be on Letterman a lot and Dave would pretty much mock him to his face.

My college roommate said he met him once and thought he was sort of a jerk but I didn’t have a huge impression of him (other than falsely assuming he was wealthy) before the Apprentice. It actually diminished my opinion of his wealth since someone who likes to bluster about being some hard-headed tough businessman but stooping to reality TV stunts that aren’t actually a measure of the contestant’s business acumen can’t be that great a businessman in actuality.

I remember that! Yeah, his bragging clearly included his supposed “wealth”. And still does.

Note the recent news that he got at least $413M from daddy. This guy has squandered an amazing amount of money.


I never saw him as a successful salesman. A successful conman, sure. Not quite the same thing (I hope). The key has often been convincing you to go into business with him to con “those” people only to discover later that he was conning you all along.

Oh, and the mob thing. Yeah, he was in business with mobsters going way, way back.

That’s a good point. You don’t see Warren Buffet hosting a show with Meatloaf and Gary Busey as stars. To the extent we thought of him at all he was this almost cartoonish person. I had no idea some people were taking his shtick seriously until recently.

I thought he was an arrogant blowhard but an insignificant figure. Famous for being famous. I heard about his bankruptcies and figured he would just fade away. Whoops.

I figured he was a typical belligerent New York con artist whose sphere of influence was limited to rich Manhattan suckers.

The techniques are the same; what’s different is what they sell.

Let’s see… first time I ever heard of him was in the 1980s, when he was notable for his supposed extreme wealth. I didn’t think much of it, other than I remember thinking that it must be a lot easier to become a billionaire if you start out a millionaire, than if you start out with nothing.

I recall that his series of wives/high profile divorces was newsworthy. Other than that, I recall him being involved in beauty pageants and “The Apprentice”, but really didn’t have much of an opinion of him other than thinking he seemed like a self-important dick.

He was, and always will be, the Avatar of Ostentation - a poor man’s idea of a rich man and a failure’s idea of a success.

I have some of those strips in a Doonesbury anthology - some of the lampooning was disturbingly close to the actual Trump.

I am so stealing that.

(On a side note, I just checked to see whatever happened to Robin Leach of “Lifestyles of the Rich and Famous” fame. Turns out he died in August of this year, age 76. In Las Vegas, natch.)

Here’s a time capsule. Al didn’t know how right he was. Glad he never lived to see Trump become president:

This pretty much sums up NY's attitude (and mine) about Trump in the 80s. I grew up here and during high school his face was always on the tabloids. No one could stand him and his buildings —it was such a symbol of the yuppie era. Who knew that this would come to define our time thirty years later?

As a Cleveland-area resident and Browns fan, I remember Trump stealing quarterback Brian Sipe for The Donald’s New Jersey Generals. After Sipe finally signed, a photo caption in one of the local papers noted that Brian was wearing his “new New Jersey jersey”, so at least the transaction produced a pun.

My brother’s friend Danny Kastner (who was known as Dan when I met him “back in the day”) appeared on Season 3 of The Apprentice and got fired in Week #3. I remember Trump saying something like “Danny’s a nice guy, but he could not lead.” I just found out Kastner now has a Wikipedia page, so his stint on Trump’s show might have opened some doors for “The Dan Man”.

He really wasn’t on my radar back then. I knew of him, but he was just kind of there in the background. Never read his book, watched his shows, etc.

Trump wishes he could have influenced rich Manhattan suckers.

Old money types and sophisticates have always seen him as a Queens-raised nouveau-riche short-fingered vulgarian who was fun to laugh at. Mock his taste in art and interior decoration. Take the free booze and hours-d’ouevres at his parties (not the good stuff, but hey, it’s free) and make faces behind his back.

This reaction from his social and intellectual superiors in New York is one of the reasons he’s such a vindictive, bitter old fuck.

“Short fingered vulgarian” I was another Spy reader. I miss that magazine.

Bombastic, narcissistic, asshole. He hasn’t aged well.

I had a vague idea of him being a wealthy media gadfly who loved to mix business and self-promotion, but I was too young to have consumed the early tabloid sensationalism and I never watched The Apprentice, so he wasn’t really on my radar screen until the birther stuff.

Said it first, said it better. I’ll just go with this. I like the term “huckster”.