[citation needed] Connolly won an at-large seat on the Boston City Council in the November 2007 election.

[7] The acknowledgement came after a Boston Herald columnist accused Connolly of sending the unsigned, unattributed flyers.

Connolly finished second of 12 candidates in the preliminary election in September 2013, behind State Representative Marty Walsh.

[14] On March 27, 2013, Menino announced that he would not be seeking election, changing the dynamics of the race, making it the first open-race for Boston mayor in thirty years.

[15] Connolly framed himself as an education-focused candidate, making improving Boston Public Schools the central issue of his campaign.

In the primary, the editorial board of The Boston Globe made a dual-endorsement of both Connolly and John Barros.

[24] Among factors credited for his loss in the mayoral general election was a last-minute half-million dollars in television advertising against Connolly and in support of Walsh, funded by the Boston Teachers Union.

Connolly was a supporter of charter schools, and his education reform proposals had run into opposition from the union.