SOUTH PORTLAND — In October 1968, appropriately dressed in an African dashiki shirt, jeans and sandals, Brad Fox was arrested for trying to deflate a tire on a police van that held his friend and fellow activist Abbie Hoffman.

Hoffman, who was by then famous as the leader of the anti-establishment Youth International Party, or Yippies, was in Washington, D.C., to testify before the House Un-American Activities Committee. Its members planned to grill Hoffman about violent clashes that occurred between police and anti-Vietnam War protesters at the 1968 Democratic National Convention. Hoffman and his wife, Anita, were arrested when he showed up for the hearing wearing a shirt that looked like the American flag.

Fox was one of the Yippies protesting outside the building, according to The Associated Press. A black-and-white photograph captured the moment when he nonchalantly pressed a tire valve with a stick to release some air. Police arrested the 20-year-old Fox and put him in the van with the Hoffmans, he said.

“I spent the night in the D.C. jail,” recalled Fox, who is now 68. “It was lovely, especially the lunch they served, which was a piece of cheese between two pieces of bread.”

Forty-seven years later, Fox is still bucking the system and fighting for underdogs as a South Portland city councilor. He has been in the news recently for helping opponents of a proposed propane gas depot at Rigby Yard, and he has upset some fellow councilors while doing it, especially when he flouted state law and city policies related to email use.

It’s the latest chapter of a captivating and somewhat controversial life that led Fox from 1960s protests in New York City and Chicago to Berkeley, California, where he eventually settled and became a public school administrator. His career and his former wife brought him to Maine in 2005, when he became a school principal in Brewer and began a period of personal and professional turmoil that stretched over the last decade.

Fox has gained some traction since he retired and landed in South Portland several years ago. His election to the City Council in November 2014 put him back in the thick of things because there’s mounting public dissent over petroleum distribution and storage operations in the city. The future of the propane depot proposed by NGL Terminal Supply Co. hangs in the balance, in large part because of Fox’s efforts, and he is unapologetic.

“I would do it all again because if I hadn’t, we’d already have a propane facility built over there,” Fox said.

FIGHTING THE POWERFUL

Fox has been railing against “the man” since he was a kid. He grew up in the Bedford-Stuyvesant neighborhood of Brooklyn, New York, the only child of a real estate broker.

During visits with his mother’s family in Virginia, Fox was shocked to see segregated public bathrooms and black residents living in ramshackle houses. He was only 12, but he challenged his uncle’s bigoted statements.

“When he talked about states’ rights (over federal intervention), I said, ‘What do you mean states’ rights? What about human rights?’ I’ve always been interested in news and politics, the way other people are interested in sports,” he said.

Brad Fox, 20, tries to deflate a tire on a police van outside the Cannon House Office Building in Washington, D.C., on Oct. 6, 1968. Inside the van were anti-war activists Abbie Hoffman and his wife, Anita, who had been arrested because Hoffman was wearing a shirt that looked like the U.S. flag. Hoffman, who was the leader of the anti-establishment Youth International Party or Yippies, was there to testify before the House Un-American Activities Committee about clashes that had occurred between police and protesters at the 1968 Democratic National Convention in Chicago. Fox, who was a Yippie organizer, also was arrested and jailed overnight. To his right is Jerry Rubin, another Yippie leader, with no shirt or shoes and a toy AK-47 slung from his shoulder.

Brad Fox, 20, tries to deflate a tire on a police van outside the Cannon House Office Building in Washington, D.C., on Oct. 6, 1968. Inside the van were anti-war activists Abbie Hoffman and his wife, Anita, who had been arrested because Hoffman was wearing a shirt that looked like the U.S. flag. Hoffman, who was the leader of the anti-establishment Youth International Party or Yippies, was there to testify before the House Un-American Activities Committee about clashes that had occurred between police and protesters at the 1968 Democratic National Convention in Chicago. Fox, who was a Yippie organizer, also was arrested and jailed overnight. To his right is Jerry Rubin, another Yippie leader, with no shirt or shoes and a toy AK-47 slung from his shoulder.

Fox went to college for a short time after high school but dropped out to join the growing counterculture movement. He fell in with Abbie Hoffman, Jerry Rubin and other prominent Yippies and began organizing demonstrations in New York City and beyond.

Fox was in Chicago when police attacked and tear-gassed thousands of protesters outside the 1968 Democratic National Convention. The Yippies nominated their own presidential candidate, an actual pig named Pigasus. When several protesters and the pig were arrested, Fox brought in another pig, Mrs. Pigasus, to beg for her husband’s release, and they were arrested, too, according to “Chicago ’68,” a book by David Farber.

Fox later moved to Berkeley, California, where he was arrested for cracking a joke to a police officer during the People’s Park protest known as Bloody Thursday, he said. A dispute over development of a public park led to a riot in May 1969, when police beat, shot at and tear-gassed about 6,000 demonstrators and then-Gov. Ronald Reagan called in National Guard troops to restore order.

“It was unbelievable,” Fox said. “The town was basically under martial law.”

SETTLING DOWN, MOVING TO MAINE

Fox eventually got a bachelor’s degree in radio and television from San Francisco State University in 1985 and operated a video production company for a while. After getting a teaching credential in 1990, he began a career in public education that quickly moved into administration. By 2002, he had a master’s degree in educational leadership from California State University East Bay and was principal of an alternative secondary school.

In 2005, Fox moved to Maine with his wife and two young daughters and became principal of Brewer High School. He and his wife had wanted to raise their children in the state where she grew up. Within a few months, they were divorced. Within a year, he resigned from the Brewer post to become principal of Camden-Rockport Middle School. Then he learned that he had colorectal cancer.

“Everything fell apart,” Fox said. “I was going through a very rough time.”

Fox started his new job and cancer treatments in tandem, sometimes wearing an intravenous chemotherapy bag while at work, he said. Before his first year in Camden was up, the board of directors for School Administrative District 28 decided not to renew his contract.

A scathing performance review said Fox had been unprofessional, showed poor judgment, failed to work well with staff, refused to follow district policies, had poor communication skills and didn’t know components of the budget, according to published reports.

Fox disputed the superintendent’s assessment and said the district failed to provide assistance during his illness. A group of parents rallied to support him, to no avail. Fox hired a lawyer and filed a complaint with the Maine Human Rights Commission.

“I thought I was doing good stuff,” Fox said. “They wanted me to leave, I said no. They said goodbye, so I sued them.”

The district settled Fox’s claim in 2009, paying him $33,000 and his lawyer $22,000, according to villagesoup.com.

BACK IN THE TRENCHES

In South Portland, Fox rented an apartment in the Brick Hill neighborhood and started working as a substitute teacher in local schools. After filing for personal bankruptcy in 2014, he was elected to the City Council to represent District 5, the western section of the city beyond Interstate 295, which he believes is neglected by city government.

“Where I live, we’re a very diverse community and it’s not reflected at City Hall,” Fox said. “I call it the Little U.N. because we have a lot of renters and minorities and new Americans.”

Fox’s concern for the disenfranchised was piqued last year when some residents grew worried about NGL’s proposal for a propane depot at Rigby Yard, which is off Route 1 between the Cash Corner and Thornton Heights neighborhoods. Some people feared that the project posed a public safety threat and was being fast-tracked for approval by city officials.

Fox responded by sharing information about the proposal through mass emails to constituents, councilors, city staff members and others. Some councilors expressed concern because Fox snubbed Maine’s Freedom of Access Act. He also insists on using a private email account rather than a municipal one, which violates a city policy. Some say Fox has fostered tension and distrust on the council and with the public.

“It’s a disrespectful and impetuous attitude that strikes me as unprofessional and certainly not in the spirit of working collaboratively,” said Councilor Claude Morgan. “It’s a mindset that says, ‘As long as we get what we want, it doesn’t matter what we do, because we’re the good guys.’ I think the lack of interest in transparency and following the rules is disturbing and erodes the public trust.”

Fox’s supporters include Councilor Eben Rose, a propane depot opponent who was elected in November. Rose said he and Fox view the council as a legislative body in a representative democracy rather than a board of directors to a corporation.

“Brad understands that going along to get along has its limits,” Rose said. “He speaks for the disenfranchised and believes they’re just as important as land and business owners. He understands that there are subtle rules of the game (that cause the system to be) stacked against the average person.”

Fox has no plans to change his approach. He wants to promote a more inclusive city government and reach out to people who have been left out. And he won’t give up without a fight.

“It’s been a wild ride so far,” Fox said. “I’m amazed I’m still alive. It wasn’t looking too good there for a while, but I’m pretty resilient.”