On horseback six days a week since March, the former Lansing-area policeman is trying to win converts to the idea that prohibition has failed and drugs should be legalized. Wooldridge claims that America's 35-year anti-drug effort has brought terror to inner cities, diverted police from more serious business, clogged the courts and prisons and ruined families.
But the problem shows no sign of going away.
"And as you know drugs are cheaper, stronger and more readily available today," said Wooldridge, a member of Law Enforcement Against Prohibition (LEAP). The organization was formed in 2002 to change drug policy. Members include former police officers, probation officers and others who worked in law enforcement.
LEAP wants to end drug prohibition laws enacted since the Nixon administration and replace them with policies that make drug abuse a medical issue. The organization contends that legalizing and regulating drugs is a more humane approach, and by taking those steps the government would knock out major criminal organizations and eliminate one of terrorism's major funding sources.
Wooldridge is riding from Los Angeles to New York, a 3,300-mile trek he hopes to complete in October. He covers 25 to 30 miles a day and is accompanied by a recreational vehicle pulling a trailer and back-up horse.
He made a trip in 2003 from Georgia to Oregon on a different horse without a support vehicle.
In the 90-degree heat Monday afternoon, the lanky 53-year-old Wooldridge dismounted along Red Arrow Highway in Bridgman to rest for a few minutes and allow his horse, Sam, to nibble the grass.
Curious passersby stopped to ask questions after seeing the horseman wearing a cowboy hat and a T-shirt bearing the message, "Cops say legalize drugs -- ask me why."
Some people disagreed, but others wanted to know more about LEAP and why a long list of ex-police officers believe drug policies must change.
"That's the way it goes," said Wooldridge, who lives in Ft. Worth, Texas. "People come out of the woodwork."
Wooldridge worked as a patrol officer and detective for 18 years in DeWitt and Bath townships in Clinton County. He became known as "Highway Howie" for his strict enforcement of drunken driving laws.
But from the start he believed that enforcement priorities were wrong, with police spending time searching cars for marijuana when more serious crimes needed attention.
His wife transferred to the Dallas area in 1994, and Wooldridge took an early retirement from police work and joined her.
He later got involved in the effort to lift drug prohibition, worked as a lobbyist in Texas, and plans to work for LEAP in that role in Washington, D.C.
Wooldridge said about 10 illegal drugs -- among them marijuana, cocaine and heroin -- net billions of dollars for drug gangs, but also for terrorist organizations. For 11 years production of illegal drugs has been the top source of funding for terrorist organizations, Wooldridge said.
Remove it, he said, "and all those Third World thugs are cut off at the knees."
Berrien County Sheriff Paul Bailey, asked for comment Monday afternoon, said he does not agree with legalizing any drug unless through a doctor's prescription.
"I think we keep fighting it and we educate people," Bailey said.
The sheriff's department's Narcotics Unit is supported by a property tax, but the millage also pays for education programs and treatment.
"I think we've made improvements in our hardest-hit area, Benton Harbor," Bailey said.
According to LEAP, more than 2.2 million Americans are in jail or prison. Each year 1.6 million people are arrested for nonviolent drug offenses, more per capita than any other nation.
He said increasingly punitive drug laws have not steered people from taking drugs, something only education and a strong sense of personal responsibility can do.
"You can't get rid of drugs. But you can get rid of the black market and the illegal drug trade," he said.
Despite the billions of dollars spent on enforcement, drugs are readily available in every part of the country, Wooldridge said.
While in a small town in Wisconsin recently, Wooldridge discussed drugs with a 14-year-old girl and her parents. The parents were surprised to hear from their daughter that she knew how to get heroin within an hour.
That does not mean the girl was using heroin, Wooldridge said, because she had the "good sense" to avoid the drug.
"At the end of the day you have to rely on personal responsibility and education," Wooldridge said.
The illegal status of drugs is at the heart of the assaults, thefts and other crime that goes with the trade, Wooldridge added.
When the United States repealed Prohibition in 1933, the national murder rate fell sharply to where had it been before Prohibition began in 1919.
The federal government is taking an ever-greater role in the drug war, and laws are becoming more Draconian, he said.
A pending bill to amend the Controlled Substances Act, sponsored by U.S. Rep. James Sensenbrenner Jr., R-Wis., would make it a felony for a person who witnesses certain types of drug activity to fail to report it to police within 24 hours.
The bill claims to intend to protect children from drug trafficking, but is in reality "a national snitch bill," Wooldridge said.
He speaks to dozens of community organizations and said the reception he gets these days is quite different than when he got involved in the effort eight years ago.
"At first people thought I was a lunatic," he said. "But over the past three years, I don't know what happened, but people started thinking, 'Maybe I'll listen to him a little bit.'"
At least some form of drug legalization, with programs for addicts managed by the government, has been adopted in Switzerland, Germany, Belgium, the Netherlands and England.
We are careful not to duplicate the efforts of other organizations, and as a grassroots coalition of prisoners and social reformers, our resources (time and money) are limited. The vast expertise and scope of the various drug reform organizations will enable you to stay informed on the ever-changing, many-faceted aspects of the movement. Our colleagues in reform also give the latest drug war news. Please check their websites often.