William Joseph Kennedy, Jr., was born in Albany, New York, on January 16, 1928, to William Joseph and Mary Elizabeth McDonald Kennedy. Kennedy grew up as an only child in a working-class family whose Irish ancestors had come to Albany five generations earlier. Kennedy’s mother worked for many years as an accountant, while his father moved from job to job as a barber, foundry worker, pie salesman, and deputy sheriff.

The older Kennedy was a regular in the saloons, political clubs, and pool halls of Albany’s North End, and, like many other young Irish Catholics, he became a petty player in the city’s great political machine run by boss Daniel P. O’Connell. As a child, Kennedy often accompanied his father, who served as a ward heeler, making rounds to the gaming rooms and meeting halls where bribery, payoffs, and crooked dealings were the custom.

On his own time, Kennedy visited the pool halls and bowling alleys and followed with great interest the careers of all the day’s legendary baseball players and hustlers. At the same time, in keeping with his Irish Catholic upbringing, the young Kennedy served as an altar boy and attended Christian Brothers Academy in Albany. After high school, Kennedy enrolled in Siena College, a Franciscan school in Loudonville, New York, where he originally planned to study chemical engineering. A failing grade in geometry, however, made him decide to switch his major to English. In preparation for a career in journalism, he served as editor of the college newspaper; he received his bachelor’s degree in 1949.

After college, the younger Kennedy accepted a position as sportswriter with the Post-Star in Glen Falls, New York. He continued his journalism career as a sports editor and columnist for the United States Army newspapers and rose to the rank of sergeant before completing his military service in 1952. He then returned to his native Albany to join the Albany Times-Union as a reporter covering city hall.

Growing tired of his job and of Albany itself, Kennedy accepted a job in Puerto Rico and in 1956 became the assistant managing editor for a new English-language newspaper called the Puerto Rico World Journal. The newspaper went out of business only a few months after his arrival, and Kennedy moved to Florida, where he briefly worked for the Miami Herald. Returning to Puerto Rico in 1957, he served as Puerto Rican...