Harold Brown liked to tell the story of growing up so poor that his immigrant mother padlocked the icebox between meals to keep her seven hungry children from pilfering food the family would need for its next meal.
Years later he was faring better. In the mid-1950s, fresh from the success of building a doughnut shop chain, he bought his first rental property — a Commonwealth Avenue apartment building. One purchase led to another as he created a formidable real estate empire that his company estimates at $2.3 billion.
One of Boston’s most storied landlords and entrepreneurs, including a few chapters he probably would have liked to forget, Mr. Brown was 94 when he died Sunday in his Brookline home of congestive heart failure.
“They’re tough,” he sometimes said of the many challenges he faced along the way, from savvy negotiating opponents to courtroom attorneys, “but I’m tougher.”
Mr. Brown had only stepped down as chairman of The Hamilton Company in September, but he remained a hands-on chairman emeritus, despite declining health.
“Intellectually he was right there up until the very end,” said his brother, Ronald of Brookline.
“And he loved the deal,” Mr. Brown’s wife, Maura Nolan Brown, said of his affinity for the real estate business, which also never waned.
At one point in the 1980s — before legal troubles, a federal bribery conviction, and an early-1990s slide into Chapter 11 bankruptcy protection — Mr. Brown’s holdings were so expansive that he estimated he collected rent from one of every 15 tenants in Greater Boston.
In the late 1980s, he told the Globe that his companies included thousands of rental units and millions of square feet of commercial space — the equivalent of several Prudential towers. Known for his charm and his business acumen, he had also moved beyond real estate to invest in Hollywood films.
“Harold was unswerving in his advocacy for moderate-income housing, in his loyalty to all those associated with The Hamilton Company, and his enormous pride in providing generous support through his foundation to many nonprofit organizations serving communities in and around Boston,” Rusty Aertsen, Mr. Brown’s successor as chairman of the company, said in a statement.
Among Mr. Brown’s many philanthropic endeavors were launching The Hamilton Company Charitable Foundation and contributing to Franciscan Children’s, which serves the medical, mental health, and educational needs of children and adolescents. About 15 years ago, the Franciscan organization honored him with a community leadership award.
His other efforts included a financial rescue, in the late 1980s, of the Coolidge Corner Theatre and donating a $2.3 million building a couple of years later to house the Fenway Community Health Center.
Though his business kept expanding in the 1980s, the decade also proved to be one of the most difficult periods for Mr. Brown and his company. He signed a consent decree, which acknowledged no guilt, to settle a US Justice Department accusation that he and his rental agent had refused to rent apartments to blacks because of their race. Meanwhile, Mr. Brown prevailed in the state Supreme Judicial Court, which reversed a Boston Housing Court judgment that found he had discriminated against federally subsidized tenants.
And in a plea bargain that spared him jail time, he admitted in 1986 that he had given $1,000 to a city plans examiner in connection with a building permit application. Mr. Brown said then that “many real estate developers and property owners, as well as I, were victimized by a corrupt system at the Inspectional Service Department, which forced us either to pay or to suffer unnecessary and expensive delays.”
In a 1988 Globe interview, he said that “as for the bribery, it was wrong,” and he added: “I don’t think you can be as active as we are without making mistakes.”
Three years later, in 1991, his company was swept up in the real estate market downturn and he filed for bankruptcy protection, hobbled by more than $650 million in debt.
“I am an optimist by nature,” he had told the Globe a few weeks earlier, adding that “patience and staying power” are essential. “If history is any guide there is going to be an up cycle,” he said. “There always has been for the last 100 years. Why should this time be any different?”
Indeed, that optimism didn’t diminish as he guided his company back to fiscal health. “We’ll be back,” he told the Globe in 1996, as he emerged from the financial cloud. “Give me another three or four years.”
Born in Boston in 1925, Harold Brown was the fourth of seven children born to immigrant parents. Their father, Morris, ran a small wood-working company. Their mother was Dora Greenberg.
Mr. Brown told the Globe that his father had arrived in Seattle in 1915 as a penniless teenager from Russia who didn’t speak English. When a customs worker inquired about his name, he didn’t understand the question.
“The official looked at my father, who was very tanned, and said, ‘Brown as a berry,’ ” Mr. Brown said, and that became the family’s name.
The family lived in Allston when Mr. Brown was born and moved to Brookline while he was a child. In a 1984 interview, he recalled dressing in a bellhop’s uniform as a boy and tap-dancing for tips. That soon gave way to $2 gigs playing saxophone and clarinet at vaudeville shows and wrestling matches.
He graduated from Brookline High School, where he played baseball and acted in plays, and from the Massachusetts Institute of Technology with a bachelor’s degree in metallurgical engineering.
Mr. Brown was a Navy officer who served during World War II and was recalled during the Korean War.
Before entering the real estate business, he had worked for a valve manufacturer and had expanded a single doughnut shop outside of Chicago into a chain. Buying that first Commonwealth Avenue apartment house changed the course of his life.
“I ended up with a lot more than the $25,000 I paid for the building and I said to myself, ‘This is a good business,’ ” he told the Globe in 2004.
Mr. Brown’s first marriage ended in divorce.
Despite his financial success, he remained frugal, including on the tennis court, where he was a very competitive player who preferred to keep using old tennis balls.
More recently, he had given up tennis for daily workouts on an elliptical machine, and at 75, he noted that he had cut back from 450 to 350 sit-ups each morning.
It was while playing tennis that he met Maura Nolan, who was a teaching tennis pro and became his tennis partner through the years. “His big statement was, before we were married it was about 50-50, but afterward, he never won a game,” she said.
They married in 1995. “He was the love of my life,” she said.
In addition to his wife and brother, Mr. Brown leaves his three children, Lisa Brown Piper of Burlington, Harley Oliver Brown of New York City, and Jameson Pruitt Brown of the South End. A funeral service will be held at 10 a.m. Wednesday in Congregation Kehillath Israel in Brookline. Burial will be private.
Ronald said his brother, who was known for his work ethic, had been “enormously creative and innovative in building a real estate empire,” and “was one of the innovators in the rehabs of older housing stock in the Boston area and supplying moderate-income housing, basically just for working-class people.”
In a Globe interview, Mr. Brown shrugged off a question about what prompted him to work so hard for so many years.
“I don’t know if there’s any driving ambition,” Mr. Brown said in 1984. “If we don’t acquire, what would we do? As in life, if you stand still, you are really going backward.”