Even with the state holding a record number of executions (19) in 2025, a Jacksonville man continues to dodge that penalty.
Jacob John Dougan, Jr., perpetrated one of the most heinous hate crimes in Jacksonville history, yet he may have set a record for escaping justice longer than anyone in America.
He was sentenced to death – three times — for the vicious murder of Stephen Orlando in 1974, the year Richard Nixon resigned as president.
But Dougan, whose first death sentence was more than 50 years ago, remains alive. The Florida Supreme Court ordered that he be given a new trial almost 10 years ago and he has been sitting in the county jail since then, waiting for that to happen while lawyers file endless motions on his behalf.
How does it take 10 years to bring someone to trial?
Orlando, who was 18 when he was killed, would be on Social Security today. He had white skin. That was the reason he was murdered.
Dougan and the four thugs who helped him torture and murder Orlando, had black skin.
Along with four other men who called themselves the “Black Liberation Army,” Dougan’s goal was to kill white people and start a “revolution and racial war,” court records show.
Evidence included a note left near the body. It was in Dougan’s handwriting and read: “Warning to the oppressive state.” Dougan also made tape recordings bragging about the murder, which cruelly were mailed to the victim’s mother and the media.
In 2016, the Florida Supreme Court upheld a lower court’s decision to grant Dougan a new trial, citing errors.
Dougan’s co-defendants were Elwood Clark Barclay, Dwyne Crittendon, Brad W. Evans, and William Hearn.
Barclay ultimately got a life sentence. Crittendon got 199 years. Evans got the same as Crittendon but was paroled in 1989. Hearn turned state witness and served only five years.
The prosecutor handling the case declined to speak to Eye on Jacksonville.
That caused us to suspect incompetent prosecution was the reason for delay.
But one local defense attorney suggested that the State Attorney’s Office may not want to hold a trial for Dougan.
After 50 years, most witnesses are dead. Any witnesses still alive could have faulty memory. Evidence may have disappeared into dusty bins somewhere.
The worst outcome would be to hold a trial and have a jury find Dougan not guilty of something he did. That would delight the anti-capital punishment crowd but would be a horrible miscarriage of justice for the victim and his family.
For some, it might be better to let Dougan die in prison at the end of a wasted life. He can console himself with the fact that he beat the system.
