Dollar Bills and Vegas Thrills

How to Get a Fine Cadillac on Her Back

Ofer Levin GTI
4 min readAug 26, 2019

Ben Stein said, “Every soul deserves a shot at a Cadillac, but not everyone should be guaranteed a Cadillac.” Well, I unexpectedly had my shot when I was a tender 21 years old. I had no idea that what was meant to be a run of the mill family visit would turn into an epic adventure, fraught with danger and disaster. I also had no idea that this would be the vanguard event that would lead to a lifelong obsession with car trips, cars, car engines and everything else to do with cars. As you may have guessed by now, this is the story of my very first road trip rand the crazy stuff that happened on it.

Uncle Gary Needed Help

Aunt Deborah had apparently called my parents to complain about the huge mess uncle Gary was making renovating the downstairs bathroom. I was persuaded to go for the long weekend to help him, under the premise that I was saving their marriage! I still think it was a ploy to get me with family so my parents won’t feel guilty for booking a trip to Costa Rica over the Thanksgiving holidays. I wasn’t complaining though, Aunt Deb’s pumpkin pie is legendary!

It’s All About the Pies

I flew to San Diego where uncle Gary picked me up, ready for a relatively boring weekend of renovating and eating (and peacekeeping!) The pie eating was going to be the good part. As suspected, there wasn’t much to do with the bathroom except some grouting which we finished off in a couple of hours. Uncle Gary cracked open a beer and, for the first time ever, offered me one as well. Then he took me to the basement garage.

Behold: Sugarplum

Sugarplum is (was) a 1960 Persian Sand Cadillac Eldorado Convertible. You may be wondering what the heck ‘Persian Sand’ is. It’s this insanely gorgeous metallic pink color a limited range of Cadillacs came out with in the 1960s. Never thought the words pink and gorgeous would come out of my mouth together but when I saw this grand beast in all its pink glory, I was gobsmacked. In fact, I drooled a little. Two beers in and uncle Gary allowed me to sit in the driver’s seat, a couple more Coors and we were revving her like there’s no tomorrow.

This isn’t my uncle’s Caddy. It’s not even the right year. But that color is still gorgeous.

This was quality time with my uncle who had a lot of stories about road trips and other adventures in the Caddy and I was all ears, just loving the pictures he was painting of an endless horizon on a long open road to distant places where adventure awaits.

And Then I Begged

I became was so besotted with this magnificent car, that I begged uncle Gary to let me drive it, but not to the corner shop as you may reasonably expect — I wanted to take her all the way to Vegas! My angle was that I had to do the trip ‘just one more time’ in honor of uncle Gary’s many fun trips to Vegas. I said, “It’s sacrilege to let her sit here in her San Diego dungeon and miss out on the bright lights!” “Just one more time, uncle Gary. I’ll take photos!”

Vegas is the Answer, No Matter What the Question is

I’m not sure how many beers it took before my uncle finally gave in. But only after he flung some dollar bills at me and made me promise to play the slots and win a million greenbacks for him. And off I went into the night in search of bright lights, showgirls and more beer.

And Then it Was Day

Unfortunately, after dollar bills raining on me, the next thing I can remember is being very sober, and upside down — and that everything was extremely bright. Yes, I was still in Sugarplum and, besides a few scratches that probably didn’t even come from the crash, I was 100% okay. Sugarplum, not so much. There I was, in a ditch with the finest cars I’d ever driven. I had no idea where I was or how I managed to roll such a massive chunk of steel! Of course, I had to call uncle Gary, who had the mother-in-law of hangovers, to come to get me.

I never made it to Vegas.

Not Even a Million Pies Could Fix This

Instead of the million greenbacks, I promised to win, all I had for uncle Gary was saying sorry a million times. I can’t quote exactly what my uncle said because it had so many cuss words in I’d risk getting banned from the internet. He was spitting mad and stayed that way for a really long time. All I could say was sorry. These days we laugh about it, but it took years to get to that. Obviously, he never offered me a beer again.

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Ofer Levin GTI

Ofer Levin GTI — Experiencing Cars and Engines. Welcome! I am Ofer Levin (aka GTI), and this is where you can read about things that matter to me.