Brennan represented part of Portland in the Maine House of Representatives from 1992 to 2000 and in the Maine Senate from 2002 to 2006. In 1992, he was elected to Maine's 37th House District. In 1994, he won re-election to a second term with 70%. In 1996, he won re-election to a third term with 75%. In 1998, he won re-election to a fourth term unopposed. In January 2002, incumbent State Senator Joel Abromson died. A special election was held in March 2002, and he ran in the vacant 27th District and won with a plurality of 41%, defeating Republican Sally Vamvakias by just 10 votes. In the November 2002 election, he defeated her in a rematch 53%-40%. After redistricting, he decided to run in the newly redrawn Maine's 9th Senate District and won unopposed. In 2018 Brennan returned to the Maine House of Representatives after easily defeating the Republican in District 36..
Committee assignments
He served as chair of the Education Committee, the Health and Human Services Committee and the Joint Select Committee on Health Care Reform. He served as Senate Majority Leader.
On December 8, 2011, Brennan led his first city council meeting as mayor. The meeting featured a 4+ hour discussion on whether to allow OccupyMaine, which was part of the Occupy movement, to obtain a 6 month permit to use two-thirds of nearby Lincoln Park. Brennan and 7 other councilors voted against the permit, while West End City Councilor David Marshall was the lone supporter of the permit. Upon the passage of Maine's same-sex marriage law, Mayor Brennan stated that he would look into the possibility of opening Portland City Hall at 12:01 AM on December 29, 2012, the day the law takes effect, to issue marriage licenses in order to have the first legal same-sex wedding in Maine occur in Portland. He also stated that he wanted to attend the first same-sex wedding in the City, whenever that might be. In 2013, Brennan was a vocal supporter of a plan to sell two-thirds of Congress Square Park to Rockbridge Capital. The plan was subsequently defeated via a citizens' initiative in June 2014 by a vote of 51.5% to 48.5%. In his 2014 State of the City address, Brennan proposed a municipal minimum wage increase. In 2015, the City Council voted in favor of a plan to increase the minimum wage to $10.68 per hour. Brennan opposed a citizens initiative to increase the minimum wage to $15 per hour by 2019. Mayor Brennan announced on June 3, 2015 that he would seek reelection but was defeated by old rival Ethan Strimling.
Personal life
Brennan lives in Portland with his wife, Joan Martay. They have two grown children, Travis and Ryan.
*Note: Through 14 rounds of instant runoffs, Brennan extended the lead he built on Election Day. During the retabulation process, second choice votes for lower ranked candidates were systematically reallocated to higher ranked candidates until an individual claimed more than 50 percent of the total.