Buying a Car


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Money Matters

May 8, 2026 by Scott Crosby

Buying a Car

There are actually a number of ways to buy a car.  Are we talking about haggling with the salesman and settling on a price being an option, or on something else?  

In this case, the focus is on just one issue:  having a particular strategy for buying a car.  There are plenty of car-buying strategies.  This has been my approach since 1981.

When I was thirty years old, I decided to buy a Cadillac.

Of course, at thirty years old, the price for a new Cadillac is stratospheric.  In fact, all my life I have considered the price of a new car – any new car – to be too high.  

Further, buying a typical average-priced car was really not what I wanted to do.  I wanted a car I could enjoy driving, and I wanted a luxury car, with lots of standard features that are not found on other cars.  In other words, a Cadillac.

S1294-1.jpgThe answer, I learned is surprisingly simple:  buy a three year old Cadillac.

That sounds simple, but the conditions of the sale make it more complex.  The goal is to buy a car that is literally “as good as new”.

What makes buying a three-year-old Cadillac is how much the value of a new car depreciates.  By the end of the third year, the price of a Cadillac depreciates by at least a third.

The second criterion is the previous owner of the car.  A doctor or a lawyer is likely to buy a new Cadillac, and then trade it in after three years for another Cadillac.  Doctors and lawyers tend to be conservative drivers, so their three year old trade-in is likely to be in good shape.  

That leads to a third criterion:  only buy a used Cadillac from a Cadillac dealer.  Doctors and lawyers do not trade in a Cadillac to buy a Chevrolet or Ford.  A Cadillac for sale on a Chevrolet dealer’s used car lot was traded in by someone who could not afford a Cadillac, which might mean that the car was not cared for properly.

The bottom line is that, using this strategy, you are able to purchase a like-new Cadillac at a bargain price.

But Cadillacs in good shape are quickly re-sold.  Get to know a long-time salesman on the Cadillac used-car lot.  Let him know what you want:  year, model, color, etc., and ask him to call you as soon as he has a trade-in that fits your parameters.  Do not accept a car that does not have your list of features.

You will need an appropriate down-payment – about a quarter of the selling price – and have a good enough credit history to get a loan to pay off the rest of the cost.

A down-payment depends on your being able to save money.  A loan depends on you building up a good credit history; i.e., always paying your bills – your mortgage, your previous loans, you credit cards, etc.  Being a financially sensible person is one of the conditions on which this strategy depends.  

Ask for a 36-month loan.  Be able to afford to pay off the loan balance in three years.

After you have paid off the loan, three years later, drop by to visit your favorite salesman.  Ask him to once again begin looking for a three year old Cadillac with the features you want.  

Do not be in a hurry; if it takes several months, that is fine.  This process works best when you are patient.  Be a buyer who consistently sticks with a particular salesman, and who waits for the salesman to do what you asked him to do.  He knows he will be making a sale, and will only call when he has a car that he knows you will like.  You will be rewarded by having first crack at any trade-in which he thinks you will want.  

You will also have the enjoyment of driving a three-to-six year-old luxury car in good shape year after year, for as many years as you use this strategy.

 

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