Whaples graduated from the University of Maryland in 1983 with B.A.'s in economics and history, and received his Ph.D. in 1990 from the University of Pennsylvania. His Ph.D. thesis, "The Shortening of the American Work Week: An Economic and Historical Analysis", won the Allan Nevins Prize from the Economic History Association.
Whaples began teaching at the University of Wisconsin-Milwaukee in 1988. He moved to Wake Forest University in 1991, and was chair of the economics department there from 2006 to 2013. He has served as book review editor of EH.Net since 1996 and was director of EH.Net from 2003 to 2008. He has argued that the United States penny should be eliminated, an argument he has supported with a study he conducted regarding the effects of eliminating the penny on prices. In 1995, he conducted a survey of economists regarding the effects of Franklin D. Roosevelt's New Deal policies on the Great Depression, and found that they were almost evenly split regarding whether his policies "served to lengthen and deepen" the Great Depression.
He and his wife, Regina, have five children (two sons and three daughters).
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