The Boston Phoenix was an icon of Boston arts and counterculture coverage for five decades. Stories and viewpoints that didn't receive coverage in Boston from other newspapers were extensively written about in The Phoenix. Major local subjects were reported on, from women’s movements, to school desegregation, and later, Occupy Boston. The Boston Phoenix wrote hundreds of articles about the Vietnam War between 1969 and 1975, including the anti-war movement, draft counseling, and the issues returning veterans faced.

As part of a larger plan to expand The Boston Phoenix to other metropolitan areas, Mindich established The Miami Phoenix on September 18, 1974, which only ran for one year before its final issue on September 3, 1975. In 1988, Mindich continued to expand the holdings of his media company, when the Phoenix Media/Communications Group (PMCG) acquired The NewPaper in Rhode Island. The paper was renamed The Providence Phoenix in 1993 and ran for nearly thirty years before the final publication on October 17, 2014. In 1993, the group grew to include The Worchester Phoenix, which ran until 2001. The Phoenix also extended into Maine with the publication of The Portland Phoenix, which ran from 1999 to 2014, before being sold to the Portland News Club LLC. In 1990, PMCG purchased Stuff Magazine, a lifestyle and arts magazine, from publisher Robert Birnbaum. On November 24, 1997, PMCG launched a biweekly arts and lifestyle magazine titled Stuff at Night, which ran until 2011. The Phoenix Media/Communications Group also bought the Spanish-language weekly El Planeta in 2008, which was sold back to its original owner in 2012.

In 1983, PMCG acquired the WLYN-FM signal and turned it into WFNX—a sonic manifestation of The Boston Phoenix. The WFNX audience was initially restricted to downtown Boston and portions of the North Shore due to Federal Communications Commission (FCC) broadcast restrictions. It initially wasn’t profitable, but the rise of grunge music in the early 1990s gave the station recognition as an alternative music hub. WFNX became the first station to air Nirvana and Pearl Jam in Boston; moving the station to the forefront of the rebellious grunge movement. DJ Kurt St. Thomas, who would later become WFNX’s program director, gave Nirvana’s album Nevermind its world premiere on August 29, 1991. The radio station sponsored numerous annual music events in the Boston area including the infamous Green Day concert in 1994 which resulted in a riot at the Hatch Shell.

Despite its commercial leanings, WFNX was quite a progressive radio station. In July 1997, as a moment of defiance against the FCC’s Safe Harbor Laws, WFNX broadcasted Allen Ginsberg’s controversial poem Howl in its entirety. The FCC declined to bring a suit against the station, marking a victory for First Amendment protections. WFNX also debuted the talk radio show, One in Ten, becoming the first commercial station to feature GLBTQA content. On July 20, 2012, PMCG sold their license to 101.7 FM to ClearChannel, and WFNX switched to online streaming. The streaming service was short-lived, as it ended on March 19, 2013 after the announcement that The Phoenix would be closing.