As a youth, Golenbock was a fan of the New York Yankees. His favorite players were Mickey Mantle and Whitey Ford. During his days at Dartmouth, Golenbock started writing about sports. In addition to writing for The Daily Dartmouth, he wrote for The New York Times and The Boston Globe. He developed a friendship with former Yankee Red Rolfe who thrilled the young writer with stories of Lou Gehrig, Joe DiMaggio, and Lefty Gomez.
A few years after graduating from law school, Golenbock was hired to work in the legal department of Prentice-Hall Publishing where he convinced the head of the trade book division to allow him to write on the Yankees. The resulting work, Dynasty: The New York Yankees 1949-64, became a best seller.
Golenbock went on to write five New York Times best sellers. Some of his most well known books are The Bronx Zoo (written with Sparky Lyle), BUMS: An Oral History of the Brooklyn Dodgers, Personal Fouls, American Zoom, and Wild, High and Tight: The Life and Death of Billy Martin. He also co-wrote Balls with Graig Nettles, Guidry with Ron Guidry, Bats with Davey Johnson, Number 1 with Billy Martin and They Called Me God with Doug Harvey.
The Forever Boys documented the Senior Professional Baseball Association, a look at major league baseball from the eyes of retired ballplayers. Golenbock spent the 1989-90 season with the St. Petersburg Pelicans for an intimate look at the league.
Golenbock wrote a children's book called Teammates, about the friendship between Jackie Robinson and Pee Wee Reese. It was selected by Redbook Magazine as one of the ten best children's books of 1990.
In 1991, Golenbock released Fenway, a history of the Boston Red Sox. He interviewed many former players for the book. He followed it up a few years later with Wrigleyville, an oral history of the Chicago Cubs, and The Spirit of St. Louis, an oral history of the St. Louis Cardinals and St. Louis Browns.
Golenbock was a radio sports talk show host in 1980 on station WOR in New York City. He was the color broadcaster for the St. Petersburg Pelicans in 1989-90 and has been a frequent guest on many television and radio talk shows including Biography on A&E, and The Fifty Greatest Athletes and The Dynasties on ESPN.