the money problems began when Duke dumped DoubleTake. "I’ll tell you literally what [Duke] said to me," Coles recalls. "This just gets me so —" he cuts his sentence short, dramatically burying his face in his hands. "I’ll try to be grown up and say I pity them, but pity is a form of anger." He pauses. "They called me in and said, ‘You’re spending the capital down.’ I said, ‘The money was given in order to get a business going.’ [They said], ‘You’re spending capital down. You can’t do that.’ I said, ‘This is our money." Coles’s voice cracks. "They have the money and I left and I took the magazine North." Does he still harbor resentment? "I wouldn’t be human if I told you I didn’t have any resentment," he admits. "‘Disappointment’ would be a polite way to describe it. But if you want to use the word ‘resentment,’ I won’t object."

In 1999, DoubleTake came to Somerville’s Davis Square, a milieu one staffer says Coles regards as "less snotty" than Cambridge, with 75,000 subscribers and 13 employees in tow. But its funding had been left behind at Duke, and with a history of money flowing in like tap water, the publication didn’t have a clue how to handle its finances. "It creates a sense of unreality," admits Coles. "You’re going on your own sweet way and you don’t pay any attention to anything because there’s a pocketful of money there." And so, publishing fundamentals were ignored: there were no substantial marketing efforts, no direct-mail campaigns, not even a sound renewal strategy; when subscriptions expired, subscribers weren’t notified.

"I think we put out a great magazine, but the numbers were declining," recalls former deputy editor Albert LaFarge. "I remember complaining to Bob, ‘Oh the circulation has fallen by half since I’ve been here.’ And he was outraged to hear that. He said, ‘I had no idea.’ I mentioned it to [then-CEO] Jim Hart, and he said something like, ‘Oh great, that’s just that many fewer issues — the printer’s bill will go down and the mailing will be less.’ The financial situation was so dire that losing a reader was almost like saving a buck."

Still, the magazine’s financial woes can’t all be attributed to lack of income. Since going independent, DoubleTake has received millions in grant support. Although it’s unclear exactly how much the quarterly has raised, two publicized grants totaling $2.25 million — from Newton’s Institute for Civil Society and an unnamed donor — came in when DoubleTake first landed in Boston. But the publication’s insistence on editorial excellence — from its thick paper stock and full-color pages to its marquee-name contributors — expended resources quickly. While most other glossies were paying freelance contributors $1 to $2 per word, DoubleTake writers earned up to $5 a word — and since some pieces ran as long as 10,000 words, a single article could theoretically cost as much as $50,000. "One of the reasons DoubleTake is so great," says current publisher Hugo Barreca, "is it’s always inclined to spend money on content and producing an excellent-looking magazine rather than on marketing."

A perfect example of how the magazine emphasizes content over practical considerations, Barreca points out, was a special issue published after September 11. "There was a philosophical reason for putting that out," he says. "But that was basically an expense of over a quarter of a million dollars. It was just an extra issue that year. It didn’t have any extra newsstand sales — newsstands had a lot of stuff on 9/11. It was basically a big cost item."

By 2002, DoubleTake had emptied the piggy bank and lost more than 50,000 subscribers. Office rent was overdue. The printer’s bill remained unpaid. The quarterly’s editorial staff — by this point, a skeleton crew of six — abandoned the duties for which they’d been hired, reorganized as a fundraising and public-relations operation, and scrambled to salvage the magazine. Last August, the Boston Globe reported that DoubleTake had shafted some freelancers by not paying them; Coles promised to remit by Labor Day. By the end of November, the freelancers still hadn’t seen their checks.

Some blame this enfeeblement on former CEO Jim Hart. One staff member recalls that a prominent DoubleTake backer wanted to contribute $20,000, and Hart never bothered to complete the paperwork necessary to receive the gift.

Regardless of who or what, exactly, was at fault, the magazine was in trouble. Lowenstein, who’d been there for fewer than six months, began fielding furious phone calls from freelancers’ agents. "‘This is an outrage,’ they’d say. ‘Yes, it is,’ I’d say. ‘You’re all frauds,’ they’d say. ‘No,’ I’d tell them, ‘we just don’t have any money.’"

BRUCE SPRINGSTEEN’S involvement with DoubleTake traces back to a dying man’s letter. In 1989, a cancer-stricken Walker Percy scrawled an admiring missive to Springsteen. At the time, the rock-and-roll star wasn’t acquainted with Percy’s work, so he didn’t answer; Percy passed away the next year. It wasn’t until 1997 — after discovering Percy’s novel The Moviegoer, an existentialist meditation on one Southern cinephile’s search for purpose and authenticity, and meeting Percy’s nephew Will backstage — that Springsteen responded to the author’s widow. "The loss and search for faith and meaning have been at the core of my own work," Springsteen wrote of The Moviegoer’s influence on him. Will Percy later interviewed the rock singer for DoubleTake in the fall of 1997. Although DoubleTake traditionally disdains celebrity, Springsteen’s musical mission matched the magazine’s inclusive sensibility. "That’s my intent," Springsteen told Will Percy. "To establish a commonality by revealing our inner common humanity, by telling good stories about a lot of different kinds of people."

That same year, Will Percy took Coles, who’d profiled Will’s famous uncle for the New Yorker, to a Springsteen performance in Lowell. After the show, they went backstage to meet the superstar; that night, the doctor and the Boss struck up an acquaintance that later evolved into a friendship. Over the next few years, Springsteen sent postcards, attended at least one of Coles’s classes at Harvard, and even stayed as a guest in his Concord home.

So last December — when DoubleTake’s mountain of debt had escalated to hundreds of thousands of dollars, and when the publication’s subscription base had plummeted to 20,000 — the staff suggested that Springsteen, or another friend of his stature, might be willing to help. "As things got more and more desperate," recalls Kicklighter, "we mustered the courage to ask Bob if maybe he could ask Bruce Springsteen to help." Coles first FedExed a letter and then called Springsteen. The singer graciously agreed to do a benefit show.

Even then, however, the magazine seemed prone to subverting itself. In January, Springsteen’s management met with DoubleTake staff to discuss the terms of the upcoming engagement. They settled on the Somerville Theatre — it was directly below the office and red tape was nominal — and ticket prices, which would range from one row of $100 seats to $5000 in the front. And although Springsteen’s reps told the DoubleTake staff "to put the word out," they apparently didn’t mean to broadcast the event to the press. "They said, ‘See how you do in terms of selling tickets at those prices.’ We interpreted that as to get the word out publicly," admits Kicklighter. "They interpreted it as getting the word out to our personal contacts. You could say it was poor communication on both sides or you could say bluntly, ‘We fucked up.’"

A few days after the magazine announced the concert, Springsteen’s representatives issued a counter-statement calling DoubleTake’s initial release "premature" and "inoperative," and said that further event confirmation would come specifically from Springsteen’s spokespeople. "Somebody’s face is beet red right about now," posted a user on the message boards of Brucespringsteen.net.

Suddenly, DoubleTake found itself on the other side of the camera lens. "Sources in Rock Land say Springsteen and wife, E Street Band guitar gal Patty Scialfa, won’t take the stage at the Davis Square theater on Feb. 20 for DoubleTake, the cash-strapped documentary maggie," blabbed the Boston Herald’s Inside Track. "We hear the Jersey couple are furious on two fronts. First, that DoubleTake, seeing Better Days ahead in the $$$ department, couldn’t wait to release the info to fuel a frenzy of ticket sales.... But what really hit a sour note with the Boss, we’re told, is the alleged $1,000 to $5,000 ticket price!"

To the public, the underlying ironies were endless. Bruce Springsteen — paladin of the proletariat, working-class white knight, real American hero — was playing an "intimate evening of music and conversation" for mainly rich folks, people who could afford to drop a bundle for a seat. And the prices were pitched to a lofty scale in order to help DoubleTake, an entity devoted — like Springsteen himself — to documenting "ordinary life," and one that had subsisted on handouts from rich people and was now strapped because it had, among other financial missteps, overpaid its contributors. The situation seemed like philanthropy at its most fraudulent: the rich and the intellectual elite were co-opting the plight of the lower-middle class for their own advantage, and were now patting themselves on the back — all in the name of "social reflection."

But that’s the story in a vacuum, without background or proper perspective. Five grand may be steep for benefit-concert tickets, but in the world of philanthropic largesse, five grand isn’t a lot — and that is the sort of environment that had begotten DoubleTake. Moreover, the magazine required around $1 million not only to cover its debts, but to plan for the future. To meet that goal in a small venue like the Somerville Theatre, ticket prices would have to be expensive, even for a two-night engagement. And Springsteen wasn’t profiting from the fundraiser; he was supporting a friend’s noncommercial project. But alas, managerial incompetence had obscured the event’s good intentions.

Ultimately, the highest ticket face value was $2500, a greater number of seats were sold for $100, and Springsteen stood on stage for nearly three hours each night for two nights, raising close to a million dollars. The raspy-voiced star answered audience questions about his creative processes, revealed the genesis of song lyrics, and, without being asked, autographed posters for Somerville Theatre workers. Still, according to Backstreets magazine, the Springsteen fans’ quarterly, during the second night’s Q&A — a period marked by gushing testimony rather than incisive questioning — one audience member inquired, "What’s the worst mistake you ever made in your career?" "This!" Springsteen reportedly retorted. "This right now."