Rappaport's career began as a Concord real estate developer, a successful occupation that largely enabled him to self-finance in his 1990 Senate attempt against Senator John Kerry. Though the polls showed early on that Rappaport, a GOP start-up, had a shot at the Senator, the campaign fizzled out by November, and he ended up losing by 13%. Rappaport was then elected as the Massachusetts Republican Party Chairman, a position he would hold from 1992 to 1997. After being rumored as a possible Lt. Governor to then-Governor Jane Swift, Rappaport jumped in the Lt. Governor's race in 2002, only to then be beaten by Mitt Romney's hand-chosen running-mate, Kerry Healey.
Mr. Rappaport remains actively involved in numerous civic and charitable organizations, including serving in a number of leadership positions for the Combined Jewish Philanthropies. He is also a member of the Board of Trustees for the Dana Farber Cancer Institute  as well as the Board of Overseers of Boston's Children's Hospital.
- "New Boston Fund, Inc. - Senior Management: James W. Rappaport - Chairman, CEO and Director". Boston, MA: New Boston Fund, Inc. Retrieved February 8, 2011.
- "Management Expertise: Jim Rappaport, Chairman". Boston, MA: Specialty Hospitals of America, LLC. Retrieved February 8, 2011.
- "Rappaport Foundation: Board: Jim Rappaport". Boston, MA: Phyllis and Jerome Lyle Rappaport Foundation. Retrieved February 8, 2011.
- "THE 1990 CAMPAIGN; Massachusetts: Accentuating the Negative". The New York Times (New York: The New York Times Company). October 31, 1990. ISSN 0362-4331. OCLC 1645522. Retrieved February 8, 2011.
|Party political offices|
|Republican nominee for United States Senator from Massachusetts
|Chairman of the Massachusetts Republican Party