Winning Back America Excerpt: AFTER SCHOOL

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My parents encouraged me to get out of the house at a relatively early age. In the summers, this meant getting a job. My first summer job was as a counselor at a sailing camp at age fourteen. I was paid in French fries and hamburgers.

When I was sixteen, I worked with two other teenagers on the Big B cattle ranch near Belle Glade, Florida, which is a town eighty miles northwest of Miami on the southeast shore of Lake Okeechobee. We were two sixteen-year-olds and a fifteen-year-old out on our own in the world, for the summer at least. The three of us lived in a little apartment above the ranch office, and we worked ten hours a day, six and a half days a week, earning $1.15 an hour for the first six days and $1.25 on Sunday—at that time, Florida agricultural minimum wage.

Most of the time, we worked clearing land for the cattle ranch. On Sundays, our job was to spot the planes that were dusting crops or killing weeds. We’d stand on either end of a field holding poles to guide the prop plane as it swooped down and sprayed. I remember feeling the cool mist of the herbicide on my bare chest as the plane went over. At the time, we thought nothing of it.

Everybody else working the ranch was Cuban. Castro had nationalized the ranches in Cuba, and these workers had come to America, dropping down a notch in status in the process. The owner of the ranch in Cuba was the manager of the ranch in Florida, the forklift operator in Florida had been the manager in Cuba, and the ranch hand in Florida had been the forklift operator in Cuba. The manager was the only one who spoke any English, so we learned to speak some Spanish (a lot of which could not be repeated in polite company, as I learned a little too late).

Another year, I worked in the back office of a brokerage house on Wall Street. In the summer, the family moved out to Long Island while my father stayed in the city to work. When we got to be old enough, each of the Dean boys worked summers in the city and lived with my father. He liked having us around. In those days, the financial services industry was not yet computerized, and my brothers and I helped keep track of the voluminous paper records.

When I graduated from high school, my father wanted me to take an extra year before I went to college, as he wished he had done himself. I followed his advice and got an English-Speaking Union scholarship to a boys’ boarding school in England.

It was a great experience, but I found the restrictive reputation of English public schools to be well earned. I enjoyed the English dry sense of humor, but a British public school is pretty cruel and the rules are strict. When I was in England, I played rugby and basketball. At home, I was by no means a good basketball player, but in the land of “football” and cricket, I was Jerry West and Pete Maravich.

This time abroad did give me the opportunity to travel, which I’ve never forgotten. I went to Tunisia for Christmas, and visited Corsica and Sardinia. A group of us drove in a Land Rover to Istanbul through Bulgaria and Yugoslavia in the spring of 1967.

To go off on my own for thirteen months at age seventeen was an eye-opening experience, and I thank my parents and the English-Speaking Union for it.