James Rappaport (born 1956) is a real estate developer, entrepreneur, attorney, philanthropist, and Republican politician from Massachusetts.^[1][2]

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James Rappaport received his education from Wharton School of Business and the Boston University School of Law.^{[citation needed]}

Rappaport initially pursued a career as a real estate developer in Concord, which provided him with the means to self-finance his 1990 Senate campaign against Senator John Kerry.^[1][2][3][4] Although early polls indicated that Rappaport, a newcomer to the GOP, had a chance of defeating the senator, his campaign lost momentum by November, and he ultimately lost by a margin of 13%. Subsequently, Rappaport assumed the role of Massachusetts Republican Party Chairman, serving from 1992 to 1997.^[2][3] While there were speculations about his potential candidacy as Lieutenant Governor under then-Governor Jane Swift, Rappaport entered the Lieutenant Governor's race in 2002,^[2][3] only to be defeated by Kerry Healey, who was hand-picked by Mitt Romney as his running mate.

Rappaport maintains active engagement in various civic and charitable organizations. Notably, he holds leadership roles within the Combined Jewish Philanthropies and serves as a member of the Board of Trustees for the Dana Farber Cancer Institute^[5] and the Board of Overseers of Boston's Children's Hospital. Additionally, he is the co-founder and chairman of the board of Specialty Hospitals America (SHA), LLC.^[6]

• United States Senate election in Massachusetts, 1990