D. Herbert Lipson, 88, who transformed Philadelphia Magazine in the 1960s from a business-promoting arm of the Chamber of Commerce to a formidable showcase for investigative journalism and the exemplar of the urban magazine genre, died Monday at the Hospital of the University of Pennsylvania.

Recently beset with heart difficulties, Mr. Lipson died following surgery for another ailment, said his son, David, chairman and CEO of Metrocorp, publisher of Philadelphia and Boston Magazines, who described himself Monday evening as in "shock."

D. Herbert Lipson
Family photo
D. Herbert Lipson

"You don't think a guy like that can die," David Lipson said. "He's a bigger-than-life character. It's just hard to believe."

Born in Philadelphia and raised in Easton, Pa., Mr. Lipson was the son of a newspaper owner, S. Arthur Lipson, who moved to Philadelphia to get into the magazine business, thinking it less hectic than newspapers. Arthur Lipson ultimately would buy Greater Philadelphia Magazine from the chamber of commerce. Mr. Lipson went to work for his father in 1953 at what became Philadelphia Magazine, one year after graduating from Lafayette College.

Mr. Lipson became publisher in 1963, and "Greater" was removed from the magazine's title four years later. He became the owner in 1968 with partner Ralph Lopatin. Lopatin died in the early 1980s, leaving Mr. Lipson as sole owner.

Wanting a publication less business-focused and more like the New Yorker or Esquire, Mr. Lipson and Alan Halpern, who would serve as the magazine's editor from 1951 through 1980, turned it into a title with impact, hiring investigative journalists. Its big break came in 1967, when one of those hires, Gaeton Fonzi, wrote an exposé about then-Inquirer investigative reporter Harry Karafin, revealing his willingness to accept payment from subjects in exchange for not writing negatively about them. Karafin later was convicted on 40 counts of blackmail and corrupt solicitation and sentenced to four to nine years in prison.

Under Mr. Lipson, especially in the 1960s and ’70s, “Philadelphia Magazine consistently did what I considered top-notch investigative reporting and broke stories that most newspapers, most news organizations, would have been proud to publish,” said William K. Marimow, a former editor of the Inquirer and now vice president of strategic development for the newspaper’s owner, Philadelphia Media Network.

The Karafin story fulfilled what drove Mr. Lipson's publishing agenda, said his son.

"He wanted to write the stories that would create the talk, which would create the conversation," David Lipson said. "That's what brought him his early success, and he never wanted to lose that. He would say to me, 'David, you got to have balls.'"

His writers loved him for that.

"Herb had a set of brass cojones. He fought for great reporting, great investigative reporting. He did it even when he got sued," said Lisa DePaulo, who worked for Mr. Lipson for more than a decade in two stints at Philadelphia Magazine. "When you look at where the magazine business is today, wow, we need a lot more Herbs. We certainly need more of them today."

As supportive as he was of reporters, he could be equally insufferable to his editors, firing several who succeeded Halpern, with whom he had "one of the greatest love affairs of all times" professionally speaking, DePaulo said.

"His most contentious relationships were with his editors," Mr. Lipson's son acknowledged. "He demanded quality. He wanted stories that had juice that would stimulate conversation. He wanted stories to cover people that mattered. He wanted bold and clean design, headlines that get people to read."

David Lipson recalled his father's telling him, "You have to grab people by the collar and tell them to read this."

Tom McGrath, the magazine's current editor, said Mr. Lipson was "a very tough guy to work for," and never left him wondering what he thought of a story once it was published. Mr. Lipson did not read stories before they were published, McGrath said.

"I would always sort of wait for the call from Herb," said McGrath, who started at the magazine in 2003 and became editor in 2010. He last interacted with Mr. Lipson about a week ago. "When he wasn't happy, he wasn't shy. When he was critical of something, as much as I might have resisted at first, he was often right."

McGrath said Mr. Lipson's influence on the magazine industry could not be overstated.

"Without him, the city magazine as a genre doesn't really exist," McGrath said.

That format had a great many fans, who took to Twitter on Monday to express their devotion to Philadelphia Magazine upon learning of Mr. Lipson's death.

The readers mattered most to Mr. Lipson — even if that meant making an advertiser unhappy, McGrath said.

"He was a good and successful businessman, but somewhere along the way he figured out, as long as he had the readers, the advertisers would follow," McGrath said. "It wasn't that he didn't care about business. He understood the readers came first."

He wasn't as steeped in the publishing industry's current priority – the move to digital. As the number of print subscribers declines, newspapers and magazines are trying to make up the lost revenue with online publications.

"He liked the internet, he liked our site," David Lipson said, but "he was still all about the magazine."

Mr. Lipson equated stories in print as having "a lot more weight, a lot more meaning," said his son, who, after graduating from Pennsylvania State University in 1978 as an advertising major, went to work for his father in advertising sales at Boston Magazine. David worked there for 6½ years before moving to New York to work with Mr. Lipson at another publication he owned, Manhattan Inc., which Mr. Lipson sold in the late '80s. David became Philadelphia Magazine's associate publisher in 1986 and publisher two years later.

Father wanted son in the business. A daughter, Sherry Litwer, joined it, too, currently working as director of home and real estate advertising at Philadelphia Magazine.

By and large, Mr. Lipson was indistinguishable from the industry that dominated his career, his son said.

"You can't talk about my father without talking about the magazine," David said. "It would be like talking about Joe Paterno without talking about football."

His hobbies were few, yet "he lived such a life," said David, 61, of Bryn Mawr. Mr. Lipson traveled extensively, often to Europe, and always stayed in top hotels, his son said.

"This young boy from Easton, Pa. — man, did he have taste," David said with a laugh. "The finest clothes, the finest food, the finest drink."

His other passion was Philadelphia itself.

"He loved Philadelphia, but nothing made him angrier than the slow progress of the city," David said.

In recent years, the magazine lost some of its luster in two race-related controversies — a March 2013 cover story by a white writer, "Being White in Philly," which drew the anger of then-Mayor Michael Nutter; and an October 2015 cover photograph of white children illustrating a story about the city's majority-black public schools, for which McGrath apologized on the magazine's website.

Mr. Lipson's unwavering opinions were routinely on display in Philadelphia Magazine's "Off the Cuff" feature. His last piece appeared in the January issue, in which he weighed in on the recent explosion of sexual abuse and harassment claims, acknowledging their seriousness but worrying about the response.

"I'm trying to understand why when we have a cultural problem to address in this country, we feel the need to beat it to death," he wrote. "…I'm afraid we're going to see various litmus tests in the workplace that, rather than promoting common decency, demand rule-bound formality."

Mr. Lipson married three times and had three children. Most recently, he divided his time between homes in Margate, N.J., and Naples, Fla.

In addition to his son and his daughter, he is survived by his wife, Carol; another daughter, Debbie Claremon; a sister, seven grandchildren, and one great-grandchild.

A private funeral service will be held Wednesday. The family plans to hold a public memorial in about a month.