Inspired by his personal bible, the Prisoners' Self-Help Litigation Manual, in Concord he picked his first legal fight. After he and others became sick from toxic paint fumes that were seeping into unventilated cells, Guglielmo convinced an inmate on a painting detail to sneak him a look at the can, to confirm that its contents were toxic. Then Guglielmo threatened to beat the prisoner unless he summoned officers.
The officers ordered Guglielmo back to his cell. Guglielmo proceeded to type up his first lawsuit.
"If you said anything," he says, "they'd give you a beating, and you'd end up in the hole. So I did what I could do, and I sued."
The paint-can lawsuit came to nothing. But the realization that he could shake authorities through the law transformed him. Driven by the same compulsive energy that almost got him killed on the outside, he because a serial litigant — smacking the institution and individual guards with suits over everything from negligence to assault and human-rights violations.
"Michael came to the view that, in order for him to survive, he needed to stand up for himself," says attorney Alan Cronheim, who represented Guglielmo as a public defender for the Manchester assault charges, and as his private counsel in prison and during his parole hearings years later. "It was his anti-authoritarian approach to incarceration, and also a way of gaining credibility and self-respect."
"The irony of my confinement," says Guglielmo, "was that I got an education in an environment that was not at all conducive to learning."
In 1989, Guglielmo formed what might be the world's most dangerous legal team.
Transferred to state prison in Somers, Connecticut, he met two fellow inmates whose smarts he could appreciate: Russell Manfredi, a Hartford cardiologist who beat his wife to death with a baseball bat, and Richard Crafts, the ex-airline pilot who famously fed his wife's body through a wood chipper. The three teamed up to battle injustice behind the walls.
Crafts, who was as handy in the print shop as he was with a wood chipper, made Guglielmo some business cards that read "Certified Legal Assistant." Working with his new allies, Guglielmo began his crusade to hold corrections officials responsible for a slew of alleged atrocities — the wholesale beating of incoming prisoners, complete with handcuffed perps being attacked by dogs and body-slammed through tables. And thanks to Manfredi, the murderous doctor, the team's reports were technically sound and medically unimpeachable.
Guglielmo proceeded to collect affidavits from anyone who observed or endured the extraordinary violence. He would maneuver to have prisoners sent to the library, the infirmary, or wherever he could safely take their testimonies and have Manfredi inspect their injuries.
In his shrewdest move, Guglielmo leaked their findings to reporters at the Hartford Courant, which followed up with a bombshell investigation that led to an FBI inquiry and the firing of two guards, one lieutenant, and even a captain.
The fallout from Guglielmo's first legal victory was harsh. Somers guards physically brutalized him, he says, and wracked him with false allegations in an attempt to scare him out of practicing law. Still, Guglielmo pushed forward, and again humiliated institution higher-ups with a suit charging that officers endangered a vulnerable inmate by bunking him with a known predator who raped him. It was the final straw. In 1993, Guglielmo was sent back to Concord.