Bob Stupak and his Caddy

Sep 29, 2009 5:03 PM
Gaming Insider by Phil Hevener |

Red Cadillac jump started Vegas career

Bob Stupak headed straight to Las Vegas when he returned to the U.S. from Australia in the early 1970s. Vegas was his kind of town, as he would tell friends and acquaintances. There was no place else he wanted to be.

The attitudes that flourished in the fertile soil of the gambling business during those years produced a perfume of sorts, a complement to his constant embrace of the outrageous.

During those years in Australia, the high school dropout from Pittsburgh had made a lot of money selling coupon books of one kind or another. Stupak lived in hotels, enjoying the good life that went with room service and maid service.

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"I liked having people pick up after me, not having to deal with my own dirty laundry," he told a Las Vegas acquaintance.

He rented a Las Vegas apartment, but several days of that brought him face to face with the grim reality of his new surroundings. There wasn’t anyone to deal with the dirty laundry issue, to provide clean towels on a regular basis. And how was he supposed to live without room service?

There had to be a better way, Stupak decided. Turned out there was. He went over to Caesars Palace and negotiated a long-term rate that made the Palace his new home. Yes, indeed, Caesars Palace was the place to be, full of the personalities and gambling that made Las Vegas his choice of towns. And there were lots of fresh towels and room service to boot.

He wandered the resort’s dimly lit corridors day and night as his moods drove him – gambling, drinking, eating, hanging out. Soaking up the ambience. There was no such thing as too much of a good thing.

And at that time in his life, he could certainly afford it. Tomorrow would take care of itself. Life beyond the Caesars front door held little interest for him.

So he’s walking through the convention area one day at a time when the leftovers from a gathering of some kind were being packed up and moved out. One of those items was a bright red Cadillac convertible. The sight of it stopped Stupak in his tracks. He walked around it. He admired it. He had to have it.

He located the person in charge of the meeting and the Cadillac and said he wanted the car. Now! The person to whom he spoke raised his eyebrows, perhaps thinking that he had heard things could happen this way in Las Vegas. A deal was negotiated and Stupak very quickly found himself the owner of that Cadillac convertible. It was a vehicle that seemed to speak his name.

But what to do with it?

Owning the car did not mean Stupak was ready to leave Caesars, to drive his Cadillac and go, well, where?

There was no place else he cared about being. So he found the person in charge of such matters at Caesars and issued these instructions: "Park it out front where I can see it from the door and feel good about having a car like this."

They did as instructed and Stupak returned to enjoying the good life at Caesars Palace for a few days or several weeks. Telling this story years after the fact, Stupak was unclear on certain elements of the time line.

But one point he makes: "I never drove the car anywhere, not even once."

What happened was one day a Caesars Palace official located him and said he was sorry to be the bearer of sad tidings, but…

Apparently, a drunk had forgotten the difference between the brake and gas pedal or whatever and had driven another car into the side of Stupak’s beautiful red Cadillac with enough force to guarantee the Cadillac would never be the same.

The incident seemed to jar Stupak, to bring him back to the surface, out of his hibernation, as it were. It was time to leave Caesars, and he did, embarking on the first steps in a long series of ventures that would forever guarantee him a place on the list of Las Vegas personalities who made a difference.

Question? Comment? E-mail me at: Phil Hevener