He received a master's degree in history from Columbia University. His thesis studied the Panic of 1873 and its effects on New York City, and focused heavily on workers' demands for public works. It was written under the supervision of Richard Hofstadter. Gutman later dismissed it as "boring conventional labor history."
Gutman was awarded a doctorate in history from the University of Wisconsin-Madison in 1959. His doctoral dissertation was on American labor during the Panic of 1873 and supervised by Howard K. Beale. During this time, Gutman worked with the eminent labor scholars Merrill Jensen, Merle Curti and Selig Perlman, who had turned the University of Wisconsin-Madison into the cradle of modern American labor studies.
He later married Judith Mara, and they had two daughters.
Gutman then took a position teaching history at the State University of New York at Buffalo beginning in 1963. At SUNY-Buffalo, Gutman began adapting more statistical and quantitative methodologies to the study of American history. But in 1964, the preeminent British social historian E.P. Thompson came to the United States expressly to visit Gutman. "Gutman's insights into the strengths of working-class resistance to industrial capitalism and the realization that one source of this resistance lay in traditions and ideas derived from previous forms of social organization made Thompson's emphasis on culture and the 'making' of the working class particularly attractive." Gutman's essay "Protestantism and the American Labor Movement" appeared in the American Historical Review in 1966. It not only put him in the forefront of the "new labor history" movement, it also cemented his already-considerable reputation.
Gutman left SUNY-Buffalo in 1966 to take a job at the University of Rochester. During this time, he conducted most of the research for his massive, path-breaking work, The Black Family in Slavery and Freedom, 1750–1925.
Gutman left SUNY-Buffalo in 1972, and became a professor of history at the City College of New York. He joined CUNY's Graduate Center in 1975, and stopped teaching at CUNY in 1975 to teach full-time in the graduate program.
In 1977, Gutman received a grant from the National Endowment for the Humanities (NEH) to teach labor history to union members. The series of lectures, called "Americans at Work," continued until 1980. The lectures attracted widespread attention from unions, workers and Gutman's peers for their engaging style, detail and application to current events in the labor movement.
The enthusiasm generated by the NEH lectures led Gutman to co-found the American Social History Project at CUNY Graduate Center. The project, funded by NEH and the Ford Foundation, began collecting original documents, oral histories, biographies and other historical documentation relating to the history of labor and workers in the U.S.
Gutman is considered one of the co-founders and primary proponents of the "new labor history," a school of thought which believes ordinary people have not received the proper amount of attention from historians. He developed a critique of the "Commons school" of labor history which focused on markets and minimize other factors such as technological or cultural changes and working people themselves.
Gutman has also been criticized for his quasi-Marxist theoretical leanings. It is clear that Gutman at one time may have been an academic Marxist. But by the late 1950s, Gutman had moved away from Marxism. Instead, Gutman retained "what he called 'a really good set of questions' that Marx had inspired (e.g., what were workers, not just leaders, doing on a day-to-day basis?). These questions reshaped labor history and also appealed to students of Afro-American history."
Gutman was often criticized for overemphasizing the experiences of working people and blacks as historical agents, and "sometimes summarily dismissed as a 'romantic' and lacking in sophisticated 'theory'…".
Gutman is best known for two major studies of slavery in America: Slavery and the Numbers Game: A Critique of "Time on the Cross" (1975) and The Black Family in Slavery and Freedom, 1750–1925 (1976).
Gutman systematically took Fogel and Engerman to task on variety of fronts. He argued they relied on evidence from a single, unrepresentative plantation. He also noted the authors were extremely careless in their math, and often used the wrong measurement to estimate the harshness of slavery (for example, estimating the number of slaves whipped rather than how often each slave was whipped). In Slavery and the Numbers Game, Gutman argued that Fogel and Engerman also routinely ignored better, readily-available data as well. Gutman roundly criticized Fogel and Engerman on a host of other claims as well, including the lack of evidence for systematic and regular rewards and a failure to consider the effect public whipping would have on other slaves. Gutman also argued that Fogel and Engerman had fallen prey to an ideological pitfall by assuming that slaves had assimilated the Protestant work ethic. If they had such an ethic, then the system of punishments and rewards outlined in Time on the Cross would support Fogel and Engerman's thesis. Gutman conclusively showed, however, that most slaves had not adopted this ethic at all and that slavery's carrot-and-stick approach to work was not part of the slave worldview.
Gutman's critique was so thorough that later reviewers called Time on the Cross "severely flawed and possibly not even worth further attention by serious scholars."
Gutman's work was widely praised. It not only constituted an excellent example of social history for its focus on individuals but it challenged long-held conventional ideas about the slavery's effects on black families. Oddly, this came just as Gutman had argued a year earlier for the relative harshness of slavery in Slavery and the Numbers Game.
Along with David Brody and David Montgomery, Gutman was editor of the Working Class in American History series at the University of Illinois Press. In the late 1980s, the University of Illinois Press established the Herbert Gutman Award for the best book in American history published by the press.