During Michael's term as an at-Large member of the City Council, and under his leadership as five-term president of that body, the City of Boston finally enacted a transgender protection ordinance, an effort which he helped lead. During his time on the City Council, Michael worked effectively both publicly and behind the scenes, along with his friends and supporters in Boston’s GLBT community, to help persuade state legislators on the issue of same-sex marriage. He became, in 2001, the first Boston citywide elected official to publicly support and endorse same-sex marriage in Massachusetts at a time when the mainstream debate focused on whether same-gender civil unions should be allowed. While the marriage bill was pending in the legislature, he organized and attended the first meeting of South Boston GLBT constituents with then-state Senator Jack Hart, organized a similar meeting with then-State Representative Brian Wallace, and personally lobbied former classmates from Boston College and Boston College High School, and other friends serving in the state legislature, to support the measure.
In a 2009 article published in Bay Windows, Michael's close friend David J. Breen -- a longtime political activist who has served on the Board of Directors of Fenway Community Health Center, DotOut, and the Massachusetts Gay & Lesbian Political Caucus -- wrote that "Michael's record on gay issues is outstanding. He was one of the first elected officials to publicly come out for marriage equality -- before the Goodridge decision," and concluded that "Michael shares our values and concerns and best embodies a new generation of experienced leadership to move our city forward".