Early Political Career
In 1976, Capuano was elected to the Somerville Board of Aldermen, representing Ward Five, the seat once held by his father. He served one term, stepping down in 1979 to run for mayor of Somerville. In the 1979 mayoral election he faced Eugene Brune, Paul Haley, and incumbent Thomas August. He lost the nomination to Brune, who defeated August. He ran again in 1981 to challenge Brune, placing second in a three-man runoff election. Capuano promoted his vote against Proposition 2½ and criticized Brune for expanding the mayoral staff in the face of tight city budgets, while Brune touted his prevention of service cuts after Proposition 2½ passed. Capuano lost in the general election with 40 percent of the vote.
Capuano served as chief legal counsel for the Massachusetts General Court's Joint Committee on Taxation from 1978 to 1984. He left the committee in 1984 to join Beacon Hill law firm and lobbying group Joyce & Joyce. In 1985 he returned to the Somerville Board of Aldermen as an at-large member.
He ran for mayor of Somerville a third time in 1989 and won the election. He served as mayor from 1990 to 1999, where he earned a reputation as a hands-on administrator. One of his priorities was to lower the city's population density, the highest of any New England municipality, by using state grants to demolish several buildings and replace them with playgrounds and parking spaces. He also oversaw a reduction in class size to 19 students.
Capuano ran for Massachusetts Secretary of the Commonwealth in the 1994 election. Capuano was seen as a conservative-leaning party outsider, running against former state representatives Augusto Grace and William F. Galvin for the Democratic nomination, and struggled to obtain support among party leaders. During the race he framed himself as an advocate for the poor and urban communities. He criticized state aid formulas which, he argued, left poorer municipalities such as Somerville and Boston with less per-capita revenue than wealthier communities such as Cambridge and Brookline. To appear on the Democratic primary ballot required the support of at least 15 percent of delegates in the June state party convention. In what the Boston Globe deemed "an embarrassing defeat", he was pushed out of the race with only 13 percent of delegate votes. When asked why he staged the difficult race to begin with, he responded, "Because I wasn't ready to run for governor."
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