Strimling's first run for public office was for the Portland City Council in 1999. He was defeated by incumbent Jack Dawson by just 24 votes. During a recount, the City Council awarded 35 disputed ballots to Strimling after his campaign argued that voters who filled in a blank line below his name had intended to vote for him. After the Council decided to preliminarily award Stimling the election longtime city councilor and former Mayor Cheryl A. Leeman commented "This is the worst example of politics that I've seen in my years in this chamber." When Dawson appealed the decision to Maine Superior Court, Strimling announced that he would step aside and Dawson was awarded the council seat. During this race Strimling mistakenly took contributions in violation of Maine campaign finance law but commented "If I had known, I'd have complied" In 2002, Strimling ran his first campaign for the
Maine State Senate to succeed
Anne M. Rand. He was elected in his first race with 74% of the vote and again in 2004 with 76%. He was elected for a third term in 2006. In the State Senate, Strimling was the Chair of the Labor Committee and also a member of the Taxation Committee. He has also served as Chair of the Criminal Justice and Public Safety Committee, and in 2006, was Co-Chair of Maine's Homeland Security Task Force. In 2008, when Democratic Congressman
Tom Allen announced that he would challenge U.S. Senator
Susan Collins, Strimling declared that he would run for
Maine's 1st congressional district. In the June 10 Democratic primary, Strimling finished fourth with 5,833 votes (out of 55,382 votes cast). He was succeeded in the Maine Senate by fellow Democrat
Justin Alfond. In February 2010, when Strimling was appointed to the New England board of the
Anti-Defamation League, he became the first Maine resident to be appointed to the position. On July 26, 2011, Strimling formally announced he was running for Mayor of Portland. Fellow former State Senator
Michael F. Brennan won the
election. Strimling and former
Republican State Senator
Phil Harriman wrote the "Agree to Disagree" column on the
Bangor Daily News website, which was named the "2013 Best State Political Blog" by
The Washington Post. They are also political analysts for
WCSH TV, working in tandem. On May 23, 2014, Strimling and Harriman wrote the last
Daily News column and started writing their column for the
Portland Press Herald on May 25. Strimling also is an analyst for
WGAN radio. On August 18, 2015, Strimling announced his intention to launch a second campaign for Mayor of Portland in the
2015 election on November 3, 2015. He won the race without needing an
instant runoff, obtaining 51% of the vote. Incumbent Mayor
Michael Brennan conceded the race at about 10 PM on election night. Strimling announced his intention to seek a second term as Mayor in the
2019 Portland, Maine mayoral election on June 23, 2019. Strimling lost to Kate Snyder. After his tenure in City Hall ended, Strimling became active in the Maine branch of the
Democratic Socialists of America. In 2020, Strimling played a leading role in People First Portland, a campaign to pass five municipal ballot initiatives to raise the minimum wage to $15 an hour, enact rent control, ban facial recognition surveillance, limit short term rentals, and a Green New Deal. Four out of five initiatives passed (only the short-term rentals limit failed) despite being outspent by the Portland business community and the opposition of Mayor Kate Snyder. In 2021 Strimling funded a
push poll showing
Maine Senate President
Troy Jackson leading former governor
Paul LePage in a hypothetical matchup in the
2022 Maine gubernatorial election with current
Governor of Maine Janet Mills also polled against LePage. == Personal life ==