
In December 1986, prosecutors in Pinellas County, Fla., had a problem. They had just failed to secure a death sentence against Jack Pearcy in the 1985 killing of 14-year-old Shelly Boggio.
The night before her nude body was found with 31 stab wounds, floating in the Intracoastal Waterway, Shelly had spent time drinking alcohol and smoking marijuana with Pearcy, his girlfriend and his two male roommates. Pearcy, a 31-year-old with an extensive history of violence against women, who had pursued Shelly in the months before her death, eventually gave a convoluted and contradictory confession that laid most of the blame on one of his roommates.
Though jurors found Pearcy guilty of first-degree murder, they recommended a life sentence rather than the death penalty that prosecutors sought — “a monumental blow,” as journalist Pamela Colloff explains in Catch the Devil: A True Story of Murder, Deception, and Injustice on the Gulf Coast, her engrossing and damning book on the case.
Securing death sentences in first-degree murder cases was the primary goal of prosecutors at the time in Pinellas County, where the nation’s Reagan-era tough-on-crime ethos found its apotheosis. Florida led the country in death sentences during this period. “But even by Florida’s standards, Pinellas County stood out,” Colloff writes. “Prosecutors sought the death penalty in nearly every first-degree murder case that came before the state attorney’s office.”
But the state had another chance to secure a death penalty — against Pearcy’s roommate, 40-year-old James Dailey. A Vietnam War veteran who struggled with alcoholism, Dailey had no connection to Shelly, and he maintained his innocence. Investigators had no physical evidence to tie him to the case, only Pearcy’s self-serving statements. So lead detective John Halliday turned to a tactic the state had used again and again: finding a jailhouse witness who would testify that Dailey had confessed to them.