Frustrated by years of wrangling with city business restrictions and what he considers infringements of his First Amendment rights, Kenneth A. O’Brien—owner of the used bookstand on Mass. Ave between Linden and Holyoke Streets—said he plans to give away his entire inventory by April.

O’Brien, who said he has spent most of his life on the streets, recently found a home in Cambridgeport with his partner and pets. But the 55-year-old said slow business has made paying the rent difficult, and now he faces possible eviction from his home.

While O’Brien said “the streets of Harvard Square can actually be as comfy for me as indoors,” he wants to trade the bustling sidewalks of Cambridge for the tranquil wilderness of the Rockies.

“Living indoors actually hurts me physically,” the Cambridge native said.

The bookstand—officially named “Almost Banned in Harvard Square Booksellers”—is registered with the Harvard Square Business Association.

O’Brien said that if he cannot clear out his remaining 15,000 books in three months, he will have someone take them away.

WANDERLUST

After completing eighth grade, O’Brien left Cambridge to pursue the vagrant lifestyle popular among young people in the 1960s and 70s.

“It became addictive for me and I stayed on it,” he said.

O’Brien said that between hitchhiking and hopping freight trains, he has crisscrossed the country and held a variety of jobs.

“I left with 40 cents in my pocket and 80 pounds on my back, came back with a lot less weight and a lot more cash,” he said. “I learned how to walk into environments and survive.”

But O’Brien said that concern for his pets and his partner, Earlene French—whom he calls “Frenchie”—prompted him to return to Cambridge and establish a home off the streets.

“I’ve gone through a year of speed when I was a kid, drank really heavily for quite a while,” O’Brien said, “but I finally quit all the craziness because I got a dog.”

But he added that he was uncomfortable in the confines of a regular job and preferred self-employment.

“I’m psychologically incapable of working for anybody else anymore,” O’Brien said. “I have a tendency now to be overcritical of things, find ways of doing things better, ways of analyzing things down to the point where people get pissed off at me and tell me to screw.”

FIGHTING THE POWER

In June 2006, O’Brien started a bookstand with his friend Gary Kibler. Shortly thereafter, Kibler was arrested by Cambridge police for allegedly violating a city ordinance that outlined the regulations for selling merchandise on the street.

Kibler challenged the constitutionality of the ordinance, saying that the First Amendment protects his right to sell books.

The judge in the case, Jonathan Brant, dismissed the city’s complaint against Kibler because of insufficient evidence.

Brant, however, ruled that while selling books is constitutionally protected, the city reserves the right to implement time, place, and manner restrictions, and identified a 50-cent peddler’s permit that would allow Kibler to continue his business. According to O’Brien, Kibler soon left the bookstand.

O’Brien said he tried to obtain this permit, but found himself mired in bureaucracy. When the city granted his request in Sept. 2006, the permit included restrictions that put him on MBTA property.

In June 2008, MBTA officials asked him to move, but O’Brien said he refused to comply unless a federal judge ordered him to do so, as the city gave him permission to operate at that location.

“Unfortunately, sometimes the city will say one thing but the city’s not always right,” said City Councillor Craig A. Kelley, to whom O’Brien has voiced his concerns. “It may take a more vigorous challenge to figure out for sure that the city’s right.”

Denise A. Jillson, executive director of the Harvard Square Business Association, said she remembered O’Brien as a man of integrity who sought to gain credibility among local business owners.

Jillson said that when O’Brien first approached her about joining the association, she was reluctant to ask him to pay membership dues. But “he came back later with cash in hand and insisted I take his money,” Jillson said.

She added that O’Brien has always paid his dues in full—even when he had to pay in installments—and was actively involved with the organization.

“He attended the annual meeting, he asked thoughtful questions, he participated in our events and tried very hard to be a member in good standing,” Jillson said.

O’Brien said he has been “in and out” of the city solicitor and manager’s offices this past fall, seeking a “legitimate” business certificate, but to no avail.

In protest, O’Brien opened a second book stand in front of City Hall in December, hoping to publicize his plight. He handed out flyers stating, “I PUBLICLY ACCUSE THE CITY OF CAMBRIDGE OF CONSPIRING TO DEPRIVE ME OF MY CONSTITUTIONAL RIGHTS!!!”

“I was hoping they would arrest me for not having a permit,” O’Brien said. “I came to the point that I realized, no matter what, I’m not going to be accepted in the business community, at least by [city] officials.”

Kelley said that he still does not understand O’Brien’s complaint and that he doesn’t recall O’Brien’s presence outside City Hall.

“I don’t know what he wanted to do and I don’t know what he needed to do to get what he wanted,” Kelley said.

A DREAM DEFERRED

While the book stand was originally intended to be a means to support his family, O’Brien said he had hoped that the business could also give other homeless people an opportunity to become self-reliant.

“The basic plan behind that bookstand is still solid,” O’Brien said. “My business plan was in three years to have six tables and 15 to 20 low-income homeless people working there, spread throughout Cambridge and Boston.”

Jillson said that O’Brien serves the homeless of Harvard Square “in a very unique and powerful way,” often providing them with advice and referrals. O’Brien, who is known to buy coffee for acquaintances when business is good, even ordained himself as a minister online so that he could feed runaway teenagers without legal repercussions.

But because of his conflicts with the city—which he says is treating him as a “second-class citizen”—he intends to shut down his business and panhandle for the summer.

“Why should I be part of a society that doesn’t want me?” O’Brien said. “I decided to stop being part of the solution and [start being] part of the problem.”

He added that soliciting in Harvard Square can actually be quite profitable.

“A single adult male can make $50 to $100 a day,” O’Brien said, pointing out that Supplemental Security Income—government assistance for low-income and disabled individuals—only provides about $650 a month.

O’Brien said he never bothered to apply for this money before, as he was wary of becoming dependent on such aid.

But because he plans to close the bookstand, O’Brien said he will accept $9,000 worth of retroactive SSI checks to purchase supplies and rent a U-Haul for his journey. He said his knowledge of herbs, tinkering, and bartering will ensure that he will never have to panhandle again.

In years past, O’Brien has offered free books during the holiday season, but always with the stated intention of reopening his stand for business in the spring. But this time, O’Brien said his decision to close shop was final.

“Homelessness is supposed to all be crazy drug addicts and unruly people,” O’Brien said. “I was trying to disprove that, but I didn’t.”

—Staff writer Michelle L. Quach can be reached at mquach@fas.harvard.edu.
—Staff writer Peter F. Zhu can be reached at pzhu@fas.harvard.edu.