His star-crossed participation in a stickup attempt in Reno, Nev., earned him 26 years in prison in an era of drastic change in U.S. justice policy, from the rise of the tough-on-crime approach to its more recent fall from favour.
Witherow shared his story during a conference in Washington, where there is bipartisan momentum behind a number of justice reforms designed to reduce prison costs and increase rehabilitation of inmates.
His initial plan, back then, was to tie down a jewelry store owner while one of his accomplices brandished a sawed-off shotgun. As it turned out, the store owner had a gun, too, and the plan went off the rails.
Witherow was eventually tracked down and sent to the slammer. Because of his seven prior convictions, mainly for robberies, he received an especially long sentence for attempted robbery with use of a weapon.
This was in 1984.
When he arrived in the Nevada prison system, he recalls, prisoners were able to get out early for good behaviour, and some of his fellow inmates were getting college degrees. Witherow himself managed to turn his life around when he got paralegal training.
But he says things changed pretty quickly.
"It was just the start of the maybe-we-should-get-tough-on-crime era," said Witherow, whose jailhouse training has helped him request pardons, push for better health care, and fight for sentencing reform as head of the Nevada chapter of Citizens United for Rehabilitation of Errants, where he's been involved since his 2010 release.
"It was all about tough on crime but nobody thought, 'How we gonna pay for it?'"
The prisons filled. Sentences grew longer, education programs were chopped.
The power dynamic shifted in jail, he said. Guards once had control because inmates hoped to earn early release for good behaviour, he said. But when those opportunities faded, he said, the gangs took over increasingly rowdy jails.
He described how a neo-Nazi gang once tried extorting money from him, then tried forcing him to join. Witherow said he responded by concocting a jailhouse rumour: that he was obtaining a knife, and would use it to stab three of them to death. The Aryan Warriors eventually left him alone.
Witherow said things started changing in the early 2000s, as Americans became concerned about the financial burden. Those concerns accelerated, he said, after the financial crisis and recession.
A federally funded study, released last week, says states' combined prison costs have increased 400 per cent since the 1970s. About 40 states have now relaxed at least some of their drug laws, and imprisonment levels have dropped in the U.S. for the first time in over a generation.
Witherow is 64 years old now, and he's feeling hopeful.
"I am optimistic that there is a pushback now," he says.
"People are finding out that tough on crime does not work."
He offers a message to Canadians when told about the mandatory minimum sentences being added to their Criminal Code: "Don't fall into the trap of tough-on-crime."