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But listeners of the Friday-night show haven't heard him complain recently. That's because for the past two months Dewey has been in the Harris County Jail, charged with failure to register as a sex offender.
After his last move, he notified Delia Hester, the Houston police officer who oversees the monitoring of sex offenders who are not on probation or parole, exactly where he would be staying.
But compliance with this law was more difficult than that. The 60-year-old military veteran could not make the round trip of 20-plus miles to Hester's Mykawa Road office to personally tell her of his change of location.
He's now looking at a potential ten years in prison because of that and another problem even more basic: How does a sex offender report his home address when he's homeless?
Critics of the offender-registration rules see Dewey, a previous rebel against the regulations, as a prime example of the inherent flaws in the complex law.
He received a 16-year sentence in 1984 for sex with the underage teen, serving five years in prison and 11 more on parole. For the last seven years of that term, he was considered such a model parolee that he didn't even have to report to officials in person, but merely sent them a letter with his address and related information.
In 2000, his parole officer knocked on his apartment door to inform him of a new Texas law. He would now have to register as a sex offender for the rest of his life. Had Dewey's parole ended just six months earlier, the law would not have applied to him.
Within a year, he decided to challenge the law. He reasoned that the Constitution prohibits retroactive, or ex post facto, punishment -- that new laws can't add to the penalties a person receives for a crime committed before those laws existed. Sex-offender registration laws were passed 15 years after he was convicted, so Dewey believed the requirements amounted to additional and illegal punishment.
Ray Hill, Dewey's friend and the host of The Prison Show, says the impacts of the law were enormous and unwarranted. "As a result," Hill says, "thousands of people like Dewey that posed no threat to anyone wound up under sex-offender laws."
Dewey informed HPD -- and announced several times on The Prison Show -- that he would no longer be registering as a sex offender. But after he was arrested at his job and jailed, he discovered that the U.S. Supreme Court had already rejected the ex post facto argument. It ruled that requiring someone to register as a sex offender was not considered punishment. Dewey wound up with a 180-day jail term.
He insists that ruling ended his days as a crusader against the law. "There's nothing I can do about it," he explains.
However, health problems almost put him back in jail last year. He complained about being dizzy and breathless, and doctors diagnosed his illness as tuberculosis. The Veterans Administration sent him to a sanatorium in San Antonio. A warrant was issued for his arrest then, but HPD's Hester got it dropped after Dewey informed her by letter that he was hospitalized.
Returning to Houston last year, Dewey stayed at Harmony House, a sort of halfway house for convalescent homeless men. In September, a grant he had from a veterans' group ran out -- and so did his luck with the registration law.
About three weeks before his arrest, Dewey says, he called Hester saying he'd be at downtown's Star of Hope Mission for a few days until he could find a job and return to Harmony House.
On November 9, Hester dispatched two deputy constables to the mission to verify Dewey was there and tell him to contact her. Two days later, they were back -- this time to make the arrest. His apparent crime is that he didn't, or couldn't, make the long trip to HPD's Mykawa Road facility in southeast Houston to personally report the change.
Activists for former inmates are hardly the only ones complaining.
"It's the very essence of overbroad legislation," says prosecutor Charles Thompson. "There are a bunch of different ways in that code you can fail to register as a sex offender. It's a very technical set of regulations."
Those regulations require that sex offenders notify HPD in person every time they "change address." Thompson adds that the city could be liable for damages if there is an incident with an offender and it can be shown that the city didn't strictly enforce the law's provisions.
Hill told attorney Sean Buckley about Dewey's situation, prompting Buckley to represent him pro bono. "There's no legislation that gives any guidance on dealing with registered sex offenders who are homeless," Buckley says.
"We've got someone who doesn't have a car, money for a cab or a bus -- if the bus even goes out there," says Buckley, "and they knew where he was."