Rappaport initially became a real estate developer in
Concord, which provided him with the means to self-finance his
1990 Senate campaign against Senator
John Kerry. 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 lost by a margin of 13%. Rappaport was then appointed
Massachusetts Republican Party Chairman and served from 1992 to 1997. After being rumored as a possible candidae for
Lieutenant Governor under then-Governor
Jane Swift, Rappaport entered the
Lieutenant Governor's race in 2002 but lost to
Kerry Healey, who was hand-picked by
Mitt Romney as his running mate. ==Current activities==