During his city council tenure, Schiff worked to ease ordinances prohibitive to small businesses, especially microbreweries, and strongly advocated against a publicly funded stadium for the Minnesota Vikings.

In January 2013, Schiff began a campaign for mayor of Minneapolis in the 2013 election but after an unsuccessful DFL endorsement convention, dropped out of the race and backed eventual winner Betsy Hodges in mid-June.

According to The Buffalo News, Schiff had painted a mural along the school's stairwell that referenced "drugs, safe sex, AIDS and racism" in the style of artist Keith Haring.

[6] The American Civil Liberties Union became involved in an extended legal fight over the constitutionality of Polka's censorship, and a New York Supreme Court Justice sided with the Lewiston-Porter School Board.

However, Robert and Rita Schiffhauer, Gary's parents, soon joined the PFLAG Chapter in nearby Buffalo, NY in order to understand and support their son which they continued to do throughout their lives.

Schiff's official public statement is that he shortened his name in an effort to move the memories of bullying that he said made his youth "an act of survival".

Wearing signs that read "$old," suggesting that their human rights had been traded for Federal grant money, Schiff and the six other students were arrested by University Police and each charged with misdemeanors.

[9] From 1993 to 1995, Schiff directed the Progressive Student Leadership Exchange (PLSE), a program modeled on the Civil Rights Movement's Freedom Summer.

[19] Schiff, at the time working as a teaching assistant in the University of Minnesota's Hubert H. Humphrey School of Public Affairs[13] on his way to earning a master's degree in urban planning,[18] took a leave of absence to run for a seat on the Minneapolis City Council against Michael Guest and Kathy Thurber in 2001.

[22] He was sworn into office on December 17, 2001, earlier than his fellow councilmembers, when Thurber resigned from her seat to assume the position of deputy director of Perpich Center for Arts Education.

[23] In his first term, Schiff sponsored and cosponsored numerous legal reforms to the Minneapolis Zoning Code that reduced bureaucratic obstacles for small businesses and housing developers, including a measure that permitted sidewalk cafes to use permanent outdoor furniture[24][25] and a change in city zoning code that facilitated the construction of denser and more affordable housing.

[30] In July 2004, the Minneapolis City Council passed a ban on indoor smoking in bars, restaurants, pool halls, and bowling alleys by a 12-1 margin.

[34] Beginning in 2008, Schiff and other city leaders contended with local ramifications of the 2008-2012 global recession, which included spate of foreclosures in economically distressed neighborhoods.

[37] In February 2012, a reporter for the Minnesota Daily wrote that Schiff is "possibly the most active and popular City Council member" and noted that 60 percent of Ward 9 voters reelected him to a third term in 2009.

[40] With colleague Elizabeth Gidden, Schiff co-sponsored the "Surly Bill," an ordinance that permits breweries to sell pints of their products on-site.

[13] The University of Minnesota's Hubert H. Humphrey School of Public Affairs hosted the first mayoral debate on March 27, with Schiff among the five declared candidates who were seeking the DFL nomination.

[57] Schiff received endorsements from the Minneapolis Firefighters Union,[58] state representative Karen Clark,[59] and former Vikings punter Chris Kluwe,[60] among others.

[61] When Schiff backed Hodges with the intention, according to the Star Tribune, of preventing Andrew from receiving the 60% of votes needed to win the endorsement, he lost the support of the Minneapolis Firefighters Union.

[71] He sits on the board of In the Heart of the Beast Puppet and Mask Theatre and has served as co-chair of the capital campaign of the Little Earth for United Tribes.