Ask Jack: Trading in Your (Chance at a) Chevy for a Cadillac-ack-ack?

Way before the book Rich Dad, Poor Dad existed, I had my own financial angel and devil on my shoulders in the form of my grandfather and mother, respectively. Granddad retired at 54 and lived more than four decades in perfect comfort based on the investment decisions he’d made prior to retirement. My mom is… well, let’s just say she didn’t retire at 54.

Mom always had champagne taste and a debutante’s contempt for anybody who did not. When my grandfather decided to buy himself a Cadillac shortly after retiring, my mother told me, in quite snippy fashion, that it was “a used Cadillac, like what a loan shark would drive.” I don’t know what I thought I was going to find in Granddad’s garage when I got there, but the six-month-old ice-blue Eldorado Biarritz that he’d actually bought wasn’t it. He took me to the grocery store in it. When we went to the register, he took out a coupon book.

“Granddad,” I asked, “why do you use coupons if you have a Eldorado with a stainless steel roof?”

“Johnny,” he winked at me, “that’s why I have one.

Shortly afterwards, my father bought a Town Car. It was brand new, which pleased my mother. But in my heart of hearts I always liked Granddad’s Eldorado better, all the more so because I knew he got it cheap. Every time I manage to buy something outrageous at a steep discount, I think of my sharp-dealing grandfather and his delight at never paying retail for anything. Which brings us to today’s questioner, who is considering following in the old man’s footsteps, after a fashion.

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  • Redapple2 jeffbut they dont want to ... their pick up is 4th behind ford/ram, Toyota. GM has the Best engineers in the world. More truck profit than the other 3. Silverado + Sierra+ Tahoe + Yukon sales = 2x ford total @ $15,000 profit per. Tons o $ to invest in the BEST truck. No. They make crap. Garbage. Evil gm Vampire
  • Rishabh Ive actually seen the one unit you mentioned, driving around in gurugram once. And thats why i got curious to know more about how many they sold. Seems like i saw the only one!
  • Amy I owned this exact car from 16 until 19 (1990 to 1993) I miss this car immensely and am on the search to own it again, although it looks like my search may be in vane. It was affectionatly dubbed, " The Dragon Wagon," and hauled many a teenager around the city of Charlotte, NC. For me, it was dependable and trustworthy. I was able to do much of the maintenance myself until I was struck by lightning and a month later the battery exploded. My parents did have the entire electrical system redone and he was back to new. I hope to find one in the near future and make it my every day driver. I'm a dreamer.
  • Jeff Overall I prefer the 59 GM cars to the 58s because of less chrome but I have a new appreciation of the 58 Cadillac Eldorados after reading this series. I use to not like the 58 Eldorados but I now don't mind them. Overall I prefer the 55-57s GMs over most of the 58-60s GMs. For the most part I like the 61 GMs. Chryslers I like the 57 and 58s. Fords I liked the 55 thru 57s but the 58s and 59s not as much with the exception of Mercury which I for the most part like all those. As the 60s progressed the tail fins started to go away and the amount of chrome was reduced. More understated.
  • Theflyersfan Nissan could have the best auto lineup of any carmaker (they don't), but until they improve one major issue, the best cars out there won't matter. That is the dealership experience. Year after year in multiple customer service surveys from groups like JD Power and CR, Nissan frequency scrapes the bottom. Personally, I really like the never seen new Z, but after having several truly awful Nissan dealer experiences, my shadow will never darken a Nissan showroom. I'm painting with broad strokes here, but maybe it is so ingrained in their culture to try to take advantage of people who might not be savvy enough in the buying experience that they by default treat everyone like idiots and saps. All of this has to be frustrating to Nissan HQ as they are improving their lineup but their dealers drag them down.