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My brother and I are going to take a road trip this weekend to go hunting for classic cars. It should be a fun trip, but he seriously has no clue why we are actually going. What he does know is that we are going to spend three days on the road zipping around the state meeting private sellers who have a classic car listed online as being for sale. My brother thinks that we are going to just spend some brother-brother time on the road together admiring a mutual passion. I think he probably should have done more reading up on classic car buying before this adventure.

In truth, he has no idea he is likely to be driving home with one of those classic cars. His wife recently got laid off from her corporate job, but got a small golden parachute and severance package with it, as she was a somewhat prominent manager within the organization. My brother knows that she is out of work, but he has no idea how much money landed in her lap, nor what she intends to do with it. Now that she is out of work for a while, as is he, she wants to take a road trip with him.

They have discussed it for a few years, and when I say road trip, I mean weeks, if not months, on the road. But she wants to fulfill a dream of his of him driving a classic car on this trip. So she told me how much money she is willing to spend on a car, but she wanted me to go along, because I am more likely to know things about classic cars and make sure my brother gets the one that wants and loves.

Which of the classic cars are we looking at will it be? I am honestly not sure. My brother is kind of a Chevy fan, but he is not particularly dedicated to one single brand, make, or model. I could list a dozen classic cars he has talked fondly of in the past.

In truth, I will not really know which one it is until we are in some guy’s garage or front yard and I see my brother’s body language. When I see the primal lust in his eyes and a price my sister-in-law can tolerate, I will start haggling the owner and then give my brother the shock of his life.