Dick Bott, 73, a retired investment banker living in Westchester County, N.Y., on his 1968 Mercury Cougar XR-7 convertible, as told to A.J. Baime.

My dad was a career Goodyear executive, so I grew up crawling around tire stores. I was a car nut almost from birth. He agreed to pay for half of my first car. When I went to Princeton, there was a rule that dated back to the days of F. Scott Fitzgerald against students having cars on campus. But my junior year, that rule changed. I said, “OK, dad, I have my half. Let’s go get a…

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