Asked if he supports marijuana legalization, an issue dear to many City Paper readers, Ein, 53, volunteers nothing more than that he has never smoked pot. He also acknowledges that he is not steeped in City Paper lore, and he struggles to recall an article that left a lasting impression.
"I wouldn't say I was a voracious reader," Ein said, adding that in his younger years he read the weekly to learn "who was playing at the 9:30 Club."
"Once in a while," he said, "there'd be a story I'd read."
Ein's purchase of City Paper has stabilized the rickety finances of a free weekly that for 36 years has served, intermittently, as an ink-stained finger in the eye to D.C. mayors, council leaders and developers.
Ein's acquisition also provided him a new platform in the District's civic swirl, where politics, business and journalism intersect.
"It gives him a political sword, depending on whether he wants to use it," said Terry Lynch, executive director of the Downtown Cluster of Congregations. "It's a vehicle for swaying local opinion."
The history of American journalism is rife with tycoons turned publishers, men such as Mort Zuckerman, the real estate developer who owned the New York Daily News until this past September, and Amazon.com founder Jeffrey P. Bezos, who purchased The Washington Post in 2013.
"We've seen it for the past 140 years going back to William Randolph Hearst, when incredibly rich people come forward and lose incredible amounts of money on publications," said Jack Shafer, City Paper's former editor who is Politico's media columnist. He said Ein "fits the bill of the vanity press mogul" who "want a public base."
"They always think they can do it better than the vanity mogul before them — that they have the special sauce to stop the losses, and it's rarely true," Shafer said. The new role, he said, can include unanticipated headaches, such as angering allies who become the unhappy focus of news coverage.
"Owning a publication is like putting a target on your back," Shafer said. "If you're Trump, you don't blame The Washington Post for coverage. You blame Jeff Bezos. When people don't like what's in City Paper, they're likely to attack Mark Ein."
Another risk: City Paper faces crushing economic pressures that have doomed alternative weeklies nationwide, an R.I.P. list that includes the Boston Phoenix, San Francisco Bay Guardian and Baltimore City Paper. Like conventional newspapers, free weeklies have lost advertising dollars to the Internet. But they face the additional challenge of getting no revenue from subscribers.
"Their audiences were aging hippies, not young people, and I don't think they renewed themselves," said Rick Edmonds, a media business analyst for the Poynter Institute. Referring to millennials, he said, "Those folks may prefer digital and may not read print newspaper or weeklies at all."
Ein declined to detail his plan for building City Paper, saying it is a work in progress that he is discussing internally and with external advisers, a group that includes sports magnate Ted Leonsis and celebrity chef José Andrés.
But one area he hopes to expand is the weekly's distribution. He also said he is aware of the city's younger demographic and his vision for City Paper includes covering "life in D.C." and ensuring the paper is available where new residents live and play.
At the same time, he also said he has no interest in influencing the paper's editorial direction and that his well-connected friends should not expect him to run interference if they don't like a reporter's line of inquiry.
"I'm not going to impose story ideas," Ein said. "My personal points of view are not going to dictate what the City Paper does."
'Mark lives large and well'
At his 2013 wedding to Sally Stiebel, then 28, many of the couple's guests — an assembly that included Sen. Mark R. Warner (D-Va.), who co-officiated, Valerie Jarrett and Vernon Jordan — danced to the Village People's "Y.M.C.A."
No, not a wedding singer's rendition.
The original group performed, the cost of which Ein declined to disclose except to say, "Not as much as you'd think."
Ein can be studiously guarded, though in a smiling, affable way. In an interview, he declined to reveal his net worth, or specify where he owns property in the Hamptons, or what he paid for City Paper, except to say it was more than the reported $50,000. He also wouldn't identify for whom he has voted, though he described himself as a centrist who has supported candidates from both parties. He has donated mostly to establishment Democrats such as Hillary Clinton, records show.
Yet Ein's life is anything but colorless. His outings with famous friends have been well-chronicled, whether it was actress Ashley Judd or former vice president Joe Biden, whom he invited to share his courtside seats at a Washington Wizards game last year.
"Mark lives large and well," said Carol Joynt, a television news producer who interviewed Ein in 2012 as part of her "Q&A Cafe" series. "He's not a jerk throwing around money. He buys things that matter to him. He is quiet quality."
During her interview with Ein, Joynt asked the businessman to cite his childhood heroes.
"When I was in high school, it was Donald Trump," he told her, adding that the developer was "sort of an icon when I was growing up."
"I think his family — I actually know some of them — I think they're terrific," Ein said, describing Ivanka Trump as "amazing" and her husband, Jared Kushner, as a "great guy."
Reminded of those remarks, Ein said: "Really? Jeez. Wow. I don't remember that."
He declined to offer an assessment of Trump's presidency, except to say that the contemporary political climate has convinced him that "serious, good, high-quality journalism is deeply important."
'Journalists aresaving our world'
Ein's holdings includes his primary residence, a 15,000-square-foot estate overlooking the Potomac River that was "inspired by the Renaissance palaces of northern Spain," a real estate agent says in a promotional video. In New York, he owns a $4 million apartment in SoHo. He also owns the Georgetown mansion that once belonged to former Post owner Katharine Graham, a place he bought for $8 million soon after her death in 2001.
In 16 years, Ein has never spent the night.
He was stymied by a neighborhood review board's objection to his designs for a two-story addition, a concept that also roiled his neighbor, developer Calvin Cafritz. "This is Georgetown — not Potomac," another neighbor sniffed to the board.
So the house remains vacant, with an annual property tax bill of $72,000, though Ein insists he still hopes to eventually move in.
Not that he doesn't get any benefits for the property, the exterior of which he allowed Steven Spielberg to shoot for "The Post," the film about Graham's decision to publish the Pentagon Papers.
In exchange, Ein said, he scored four tickets to the Washington premiere.
Ein grew up in Chevy Chase, Md., and is well-grounded in local history. His father, Dan, is a prominent allergist and his mother, Marion, is a health-care consultant who survived the Holocaust. Ein graduated from the Wharton School of the University of Pennsylvania and went to Harvard Business School before working at the Carlyle Group and Goldman Sachs and striking out on his own.
In all of his investments, Ein said, he prefers a hands-off management style and settling in for the long-term. He promises a "long runway" for City Paper, which he bought after the weekly's owner, SouthComm, threatened to cut staff salaries by 40 percent in December and its editor, Alexa Mills, got in touch with him.
His advisers on the purchase, before and after, have included a cross-section of Washington associates, from 9:30 Club owner Seth Hurwitz to City Paper alumnus Jake Tapper of CNN to Harry Jaffe, the Washingtonian writer who at first told him, "Don't do it."
"Then I changed my mind," Jaffe said, noting that a need exists in the District for local journalism with the demise of the website DCist and bankruptcy of the Current newspapers.
Since Ein's purchase, City Paper is hiring, and it announced the addition of Tom Sherwood, the veteran political reporter who recently left NBC4. Ein said the support he has received reflects the public's growing appreciation for journalism.
"I'm troubled by the attacks on the press, the norms and the institutions of our country," Ein said. "To some extent, journalists are saving our world."