Five of the last seven Massachusetts governors have been Republicans. The Republican Party is so small that it requires independent (unenrolled) voters to win. This aligns with these voters, particularly those of those who are unenrolled or independent. The success of this strategy can be attributed to strong connections with voters and financial resources. This year, Gov. Maura Healey will be challenged by three Republicans, one of whom will be endorsed at the Republican Party convention. Republican Gov. Bill Weld (1990 -1997), Mitt Romney (2002-2006), and Charlie Baker (2016-2024), all Republicans, were elected to two terms respectively.