Before he was "No Money" Mike, people called Connolly "Big Mike" — starting in middle school. By the sixth grade he was so tall that he exceeded the size limit for Pop Warner football. Though Connolly spent his early years in Milton, his parents divorced when he was five, and he and his mother moved to Norwood. There, he was raised in the Jefferson Drive housing projects, a bleak duplex wasteland off Route 1 where he remembers cops regularly ramming down doors and people fighting in the streets over drug debts.
By middle school, Connolly was excitable and mischievous. But after years of causing trouble, he says he finally smartened up in time for ninth grade. In 1992, Connolly's father brought him to the Boston College football team's home opener against Rutgers, and the experience left a lasting impact. "It changed me overnight," he says, his smile stretching wider than usual. "My dad was back in my life, and I immediately made up my mind that I was going to get a college scholarship."
Following a star turn as a Norwood High School Mustang, Connolly accepted a full ride to play offensive line at Duke, where he led a triple life as a jock, a political junkie, and a computer-science major with sights set on the tech boom. After graduation, Connolly took a job with an electrical company in Norwood, only to find suburban office life less than fulfilling. "I was making a good living, but after a while, it wasn't enough for me," he says. Connolly currently works for a Hewlett Packard–owned software company in Boston, where he manages custom applications built for law firms. "At the time, I thought that I could go to law school, get a job making $180,000 a year, change the world, and have it all."
Connolly's bourgeois fantasy imploded with the housing bubble, and in 2008, after graduating from BC Law, he was laid off by a Boston real estate law firm — before his contract even started. In the following years, he stepped back from the lure of luxury, and began working for the US Census to pay school loans while embracing his progressive instincts on the side (he also started playing lead guitar and singing with the funny Cambridge folk band Pelvis McGillicuddy). That all led him to Rootstrikers, a group that Harvard Law professor Lawrence Lessig founded to "fight the corrupting influence of money in politics," and after that to Occupy, where he showed up for the initial planning meetings and went on to join the legal working group. A year later, Connolly's Facebook page still features a picture of him beaming on the first Occupy Boston march, his meaty fist raised higher than any sign in the crowd. "Occupy was like that Boston College game," he says. "It changed my life forever."