Donald Trump often suggests that his greatest asset is his name, which he personally has valued at over $3 billion. What’s less commonly known is that the very first time he slapped his name on any product, it was on a pair of Cadillac limousines known as the Trump Executive Series and the Trump Golden Series. And he got Cadillac to build them for him by agreeing to order a run of limos he never bought.

Trump’s automotive ambitions were mentioned in his well-known ghostwritten book Trump: The Art of the Deal, in a section titled “The Trump Car”:

“A decision has been made to go into production on two Cadillac-body limousines using my name. The Trump Golden Series will be the most opulent stretch limousine made. The Trump Executive Series will be a slightly less lavish version of the same car.

Neither one has yet come off the line, but the folks at Cadillac Motors Division recently sent over a beautiful gold Cadillac Allanté as a gift. Perhaps they felt I needed more toys to keep me busy.”

The “most opulent stretch limousine made.” Even then, he had a gift for hyperbole.

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Soon, that pair of custom Trump-branded limousines did come off the line, and was unveiled at the Limousine and Chauffeur Show in Atlantic City in 1988. During the presentation, here’s what Donald Trump had to say, according to an issue of Limousine, Charter & Tour from that year:

Well, this began about two years ago when John and I were in Palm Beach. And I was saying “John, what Cadillac ought to do is come up with a design for an incredi­ble limousine that has the big headroom and all of the assets that anyone, could want.”

Later, I got a call from John and he said “Would you like to get in­volved with this design project?” I said “I know nothing about cars ex­cept what I personally like...” But be­tween myself, Cadillac, and John Staluppi at Dillinger...we went ahead and designed the car.

We built one, and we saw a lot of things we didn’t like. So we went back (several times), and this is what we produced. And we think we prob­ably designed the ultimate limousine to be found anywhere in the world.

You can see the kind of quality there is. We left nothing out. I’m very honored that they built me the first one and, frankly, I deserve it. I really am very honored and I would like to thank Cadillac and everyone else in­volved.

The best limo in the world didn’t exist, so Trump made it. Because he deserved it. Or so he said.

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The John Staluppi he refers to is a businessman, yacht and car collector, and someone with alleged ties to organized crime—the New York Daily News reported the FBI at one time identified Staluppi as a member of the Colombo family.

Staluppi that ran the company, Dillinger Coach Works (named after exactly who you think it’s named after), which did the conversion work on the limos. The Smoking Gun has a more extensive explanation of the supposed mafia ties of Trump’s partners.

The limos were pretty much exactly what you’d expect from a 1988-era Donald Trump, or today’s Donald Trump: luxurious, over-the-top, and with gold slathered over everything that stayed still just for a moment.

Pictures courtesy of FleetofCads

These limos had rosewood interiors and were equipped with a fax machine, TV and VCR (so you could tape Dynasty and watch it at your leisure), a paper shredder, writing desks, a pair of early NEC cell phones, and a cabinet with glasses and the delightfully-named Perm-a-Pub liquor dispensing system, for keeping everyone nice and liquored up while deals are getting done.

The exteriors were also suitably Trumpified, with larger grilles with vertically-oriented slats, sort of vaguely Rolls-Royce-ish, an enlarged greenhouse for more headroom (likely to provide arm/equipment clearance for the intense hair maintenance Trump requires), a large stainless-steel B-pillar panel, and, on the Golden Series, gold plated trim all over the place, including gold-stripe tires by Vogue.

Pictures courtesy of FleetofCads

So, sure, these are exactly the sorts of limos you can imagine Trump wanting. A recent story by Automotive News points out he said he wanted them so much, he arranged with Cadillac that if they worked with him on making them, he’d buy 50 limos for his personal use and to shuttle bigshots to and from his casinos in New York and Atlantic City.

This is bit different than how Trump portrays the arrangement in the book, which makes it sound more like Cadillac was just thrilled to build a Trump-branded limo, with gifts of gold Allantés and no mention of a 50-limo order.

But the GM’s Cadillac division at the time, John Grettenberger, told the story differently. Here’s what he wrote in his hard-to-find book Ready, Set, Go! My Life at General Motors, Cadillac, Oldsmobile, Opel, and Isuzu, again via Automotive News:

“He would input to the interior styling of the vehicle and allow Cadillac to use his name in promotional activity. By doing so he intended to purchase 50 of them for his personal use.

He was looking for means to transport high rollers from New York City to his hotel and casinos in Atlantic City and return.”

According to Grettenberger’s take, it seems like the order of the 50 cars was what made Cadillac open to the arrangement, along with Cadillac’s use of Trump’s name—which, to be fair, was a desirable commodity in 1987-1988, prior to Trump’s 1991 bankruptcy.

That’s why the way the Trump Car deal played out is so interesting. Also from Grettenberger’s book:

“The two prototypes were built but when it came down to approving the transaction and placing a purchase order for the fifty limos, nothing happened!

Donald gave all sorts of reasons for a delay, purchased one for “his father,’ but no order for the remaining forty-nine. I’m not even sure what happened to the second prototype.

So much for the Trump limousine!”

So, when it came down to Trump actually closing the deal and buying the promised 50 limousines, apparently Trump graciously decided to buy... one, which he said was for his dad. Allegedly, he didn’t even buy the whole initial production run of two, reneging on 49 Trump Limousine orders and effectively killing the whole project.

It’s not just Grettenberger who was expecting to build more than two of these land yachts; contemporary news reports like this AP article of the era suggest that “Several hundred of the limousines may be produced annually,” and that the limos would cost between $55,000 and $65,000 (or between $112,000 and $133,000 in today’s money).

Nobody seems to know where the second prototype is (the other one seems to be in the hands of a European collector, which explains the modified headlights and taillights), and Cadillac really got nothing at all out of the deal.

What we do know is that Cadillac never got the order for the full run of 50 cars, and never got to make use of Trump’s name in any promotional or advertising context.

If you step back and look at the Trump Car “deal,” it could easily cause you to wonder if Donald Trump got Cadillac to take the considerable time and effort to design and build him (or, sure, his dad) a custom limousine at essentially no development cost to himself, beyond the purchase price of the final car.

If one did follow this line of reasoning, one could also note that he even managed to get his reportedly mob-connected friends at the Dillinger Coachworks company some cash out of the deal.

One way or another, Trump ended up with the very fine personalized custom limo, the one he wanted in the first place.

I hope this has been a good lesson in the exquisite Art of the Deal.