Touring the downtown offices of Sun-Times Media with Michael Ferro, its chairman, is like chasing a newspaper being blown across an O’Hare runway. We zip through glass doors that open with a click when he presses a keycard onto metal plates, into the Wonka-esque wonders of the candy and ice-cream room he ordered built for employees last year, and then through the blinging, pinging foosball and Pop-A-Shot game room he also had installed. “This [game room] is the new water cooler,” Ferro says, his voice an almost urgent rise and fall in which every fourth word seems underlined, traces of a Long Island accent still evident.

We breeze through the corner domain of the Chicago Reader, the alternative weekly for which Ferro and his partners shelled out nearly $3 million in May 2012. (“The Reader is what we wish everything was like. Self-sufficient. They make money. Great morale.”) We float through the vibrant blue-walled environs of Ferro’s year-old baby, the weekly magazine Splash (“Chicago’s Dose of Style, Society, and Celebrity”). And then to the office of Ferro himself.

Seemingly guarding the entrance is a life-size mummy fashioned from folded dollar bills, lying on its back in a rectangular glass case.

“Oh, that,” Ferro says with a wave of a hand when I ask about it. “It was created by Scott Campbell, this renowned tattoo artist. I thought it would be funny. Everyone else thinks that it used to be full of money and we’ve been carving it out to pay for everything and this is what’s left: the carcass. To me, it means either you can’t take it with you or the death of paper.”

In December 2011, this wealthy tech entrepreneur became the unlikely lead investor in Wrapports, a holding company formed by a dozen prominent Chicagoans to purchase the owner of the Chicago Sun-Times. (The CEO is former Newsday and Chicago Tribune exec Timothy Knight.) Some $20 millon later, Ferro and company controlled the second-biggest newspaper in the third-biggest city in the nation, the hallowed home of Mike Royko and Roger Ebert and eight Pulitzer Prizes, the epitome of a tough blue-collar underdog.

Turns out Ferro stood at the forefront of a trend. The ensuing months witnessed a flurry of other rich men without media experience snapping up important newspapers—including, in August alone, Red Sox owner John Henry’s $70 million purchase of The Boston Globe and Amazon founder Jeff Bezos’s $250 million purchase of The Washington Post.

If reporters thought that Ferro’s entrance into their world would make him more accessible—he hadn’t agreed to an interview since the twin towers stood— they were wrong. He wouldn’t even grant his own newspaper an interview. Last year he backed out of a scheduled Q&A with this magazine at the eleventh hour. When I told his representatives that I was doing a feature on him and the Sun-Times with or without his cooperation, he finally capitulated.

And so on a sweltering September morning, I head to the concrete riverfront building that houses Wrapports and the Sun-Times (where I worked as a reporter from 1997 to 2003). On the 10th floor, I approach an art-gallery-chic reception area occupied by two female assistants wearing short skirts and high heels. (Several staffersr efer to them as Ferro’s Angels.) “Who did you say you were?” the blond one asks me with a frozen, uncertain smile. I wonder whether this interview is about to get canceled. Again.

But after a few minutes Ferro appears, sporting a silver-flecked goatee, rectangular Ralph Lauren eyeglasses, an open-necked shirt, and a dark blazer with a subtle windowpane check—a uniform adopted by Silicon Valley hipsters a decade ago. Trailed by a smiling PR rep and by Sun-Times editor in chief Jim Kirk, he pumps my hand once, making a flicker of eye contact before jamming his hands in his pockets and striding toward the door for that breakneck office tour.

Ushered into his office afterward, I’m surprised by how small it is. It contains two black leather chairs, two modern white ottomans, and a green tempered-glass desk, the surface of which holds not one scrap of paper. Holds nothing, in fact, but a small tablet computer. “This is actually kind of dirty for me,” Ferro says with a straight face. “I’m a guy who does not like messes.”

Yet he is nearly two years into one of the messiest industries around. Newspaper revenues continue to erode, and the smartest media minds around the country still have not found a convincing business model. The Sun-Times continues to bleed red ink. As Ferro burns through investors’ money and alienates many of his own employees, some wonder if he is really cooking up a viable digital model to ensure the survival of the Sun-Times or whether he’s just another ego-driven entrepreneur who cares more about hanging with celebrities than about quality journalism.

There’s no arguing that Ferro has a lot on the line, including tens of millions of his own money and his credibility with some of the most powerful people in town. The citizens of Chicago have much at stake too. Uncertainty shadows the city’s only other major daily, the Tribune (owned by the Tribune Company, Chicago’s parent). Tribune is in the midst of splitting itself in two: its newspapers and other publications in one company, its faster-growing broadcast and digital properties in another. Wrapports—at least at one point—was angling to buy Tribune assets. (As a condition of our interview, Ferro would not answer questions involving Tribune. A Tribune spokesperson also declined to comment.) Bottom line: For anyone who cares about the future of journalism in Chicago, what Ferro does matters.

When I ask Ferro’s employees and associates what he’s like, they tend to chuckle ruefully, sigh, or groan. Detractors say he has a scattered, almost manic energy that manifests as a short fuse, an impatience that prevents ideas from blossoming, even downright rudeness. One former Sun-Times editor relates Ferro’s early 2012 introduction to then metro editor Shamus Toomey (who has since joined a growing exodus of the newspaper’s top staff to DNAinfo, the hyperlocal news website started by Joe Ricketts, patriarch of the family that owns the Chicago Cubs). Ferro, without making eye contact, gave Toomey a quick handshake and said, “Nice to meet you, James.”

Ferro is “a fire hose of thoughts and ideas and opinions and expressions and unwarranted challenges to orthodoxies that didn’t need to be challenged,” continues the editor (who, like many other journalists I spoke to, asked not to be identified for fear he could hurt his career). “He’d come up with ideas where we’re thinking, OK, we’ve already tried that, and here, let me show you the disastrous results. I give him credit for trying a lot of things, but so often it was about snap judgments. you’re dealing with a guy who isn’t really interested in dialogue or opinions other than his own.”

Jim Kirk, a longtime Chicago business editor who was hired as the Sun-Times’ editor in chief and senior vice president in May 2012, admits that he had his doubts when Ferro first approached him. “I almost didn’t take the job,” Kirk says. “He likes to be critical of things he doesn’t think work. And there was a lot of criticism of traditional media in general. And in the discussion, I’m thinking, He’s criticizing a lot of places I’ve worked at [including the Tribune and Crain’s Chicago Business]. I don’t think that’s going to work.” Eventually, Ferro won him over.

Ferro’s supporters don’t deny that he has “ants in his pants,” as one put it. Indeed, they believe that it’s part of what has made him successful. Guy Chipparoni, president of the Chicago public relations firm Res publica Group, who has worked for Ferro, likens him to the old cartoon of “a neutron and a proton meeting each other in a sock drawer—bing bing bing!” Even John Canning Jr., the initial driving force behind the purchase of the Sun-Times and a man whom Ferro reveres, recognizes his protégé’s distracted energy. “I kind of to his face described him as Rain Man,” says Canning, the cofounder and chairman of big private equity firm Madison Dearborn Partners. “He’s got all these ideas, and he really needs a short-handled-broom man to just kind of pick out the brilliant ones and get rid of the rest of them.”

By all accounts, Ferro has grown to relish the spotlight of fame that media ownership brings—as long as he is the one controlling it. (“I just like my privacy,” he tells me.) He has rubbed elbows with actor Jim Belushi, rapper Lupe Fiasco (who calls him “a genius”), and former Playboy centerfold Jenny McCarthy, all of whom he has persuaded to write a rotating column. Invitees to his lavish 47th birthday party at Chicago Cut Steakhouse in July included Mayor Rahm Emanuel and “what looked like a convention of CEOs,” including Aon CEO Greg Case, former UAL CEO Glenn Tilton, and McDonald’s chairman Andrew McKenna Sr. (also a Wrapports investor), reported Crain’s Chicago Business.

Photographs of Ferro have appeared prominently in his own publications, including one in the Sun-Times of his family at a 2012 Cubs game—a photo that disturbed many who value the importance of editorial independence. “Is this Ferro dude for real?” marveled Robert Feder, a longtime Chicago media critic who once worked at the Sun-Times (and whose blog recently began appearing on the Tribune’s website), in his column at the time. “By what stretch of the imagination could anyone consider it newsworthy that the owner of the Sun-Times attended a Cubs game with his family?” (Kirk says the decision was made by editors in the newsroom.)

At different times during my tour with Ferro, and later during our sit-down interview, I see glimpses of what everyone talks about: the impatience, the malapropisms, the hands in and out of pockets and thumping the table to make a point, the obvious flashes of boredom, the exasperation at questions he either doesn’t like or thinks are dumb, the rising voice when he feels put on the spot. It’s clear that he’s not used to being challenged. It’s clear that this interview is risky for him. But he doesn’t shy from a single question.

Ferro grew up in Merrick, New York, a commuter town halfway between Manhattan and the Hamptons that is perhaps best known as the hometown of Amy Fisher, a.k.a. the Long Island Lolita, and of disaster-prone actress Lindsay Lohan. Ferro’s father, who worked in real estate (his mother was a homemaker), got a job in the Chicago area when the boy was 15.

With his parents and two sisters, Ferro moved from Merrick to the western suburbs, where he enrolled in Naperville North High School. By the time he graduated, Ferro says, he had already chosen his career: “I wanted to run companies.”

While still at Naperville North, he launched a roof-sealant business that eventually grew to 70 employees and would help pay his way through college. At the University of Illinois at Urbana-Champaign, he studied psychology. “I was just having fun,” Ferro says, explaining why he chose the major. “What I really wanted was to be in computers.” He began to dabble in programming.

In 1992, Ferro sold his company, Chem Roof, to an equipment manufacturer in Lisle for a sum he declines to disclose. And then, in 1996, he launched the venture that would change his life. Click Commerce (initially named Click Interactive) provided software programs to businesses that helped them with marketing, commerce, communication, and more. Click landed such big clients as Motorola and the motorcycle maker Kawasaki. With a bravado that would become his trademark, Ferro told a Sun-Times reporter that $1 trillion in commerce could be conducted in the near future by companies using click commerce’s software suite.

That never happened; not even close. But Click was enough of a hit to make Ferro a new darling of Chicago’s moneyed set. He cemented his reputation when he took the company public at exactly the right time: in 2000, just before the dot-com crash. On paper, the IPO made him a millionaire many times over. Later, in 2006, Illinois Tool Works paid $292 million to acquire Click, with Ferro clearing a cool $65 million.

In short order, Click tanked. ITW wrote off its investment. But Ferro had already moved on. With the windfall, he set up his own private equity firm, Merrick Ventures. “I did it because a lot of members of the community came forward and said, ‘We want to work with you in tech,’ ” he says.

Ferro placed one of Merrick’s big bets in 2008, in the midst of another stock-market crash. The firm paid a reported $20 million for a controlling stake in publicly traded Merge Healthcare, a health records and imaging software company that was on the brink of bankruptcy. Ferro became Merge’s chairman, moved its headquarters from Milwaukee to Chicago, and replaced its CEO, among other changes. The market cheered, sending the stock soaring from less than 50 cents a share when Ferro bought in to more than $7 a share by September 2011.

Alas, Merge would hit turbulence, too: Its stock price began to tumble around the same time that questions were being raised about deals between Merge and other firms controlled by Ferro. According to reporting by Crain’s Chicago Business last year, Merge’s audit committee of independent directors reviewed only four of 11 transactions with companies in which Ferro has an interest. While not illegal, that’s a no-no in good-governance circles because such deals may fail to maximize shareholder value.

“The related-party transactions had nothing to do with the stock-price decline,” responds a Merge Healthcare spokeswoman. She adds that the number of transactions reviewed by the audit committee, as reported by Crain’s, was “factually inacurrate.” Ferro declines to speak about anything related to the company, citing plans to take it private.

In August, Merge reported quarterly results so dismal that Ferro took the drastic step of publicly apologizing and stepping down as chairman. At presstime, the company was trading at $2.68 a share.

But well before then—when Ferro was still riding high—he received an intriguing phone call. On the line was Ferro’s mentor and champion, John Canning Jr.

Over the years, Canning and Ferro had partnered on several investment deals. More than that, they had become good friends, serving on many of the same civic and philanthropic boards, including those of the Field Museum and the Museum of Science and Industry. Their wives, too, had become close. (Ferro married Jacqueline, now 42, in 1996; they have three children, ages 16, 14, and 12. The family lives in a Gold Coast high-rise, making frequent getaways to homes in Lake Geneva, Wisconsin, and in Palm Beach, Florida.)

Canning enjoyed socializing with the feisty young tech entrepreneur. “I thought, He has a pretty good sense of humor,” Canning told me. “It’s a self-deprecating humor. He’s able to laugh at himself. He’s kind of a free spirit.”

One of the ventures for which he and Ferro had teamed up was the Chicago News Cooperative. Led by James O’Shea, a former managing editor of the Tribune, it started in 2009 with a noble mission: to create and sell news stories about Chicago on a nonprofit basis, possibly creating a new model for public interest journalism. Though the cooperative scored the prestigious job of supplying stories to The New York Times, the effort was ultimately untenable. It folded in February 2012.

With the Sun-Times floundering in the wake of the unexpected 2011 death of its owner, James Tyree—the popular Mesirow Financial CEO who had bought the bankrupt paper two years before for $5 million and the assumption of about $20 million worth of debt—O’Shea saw an opportunity. He argued to Canning that the newspaper was worth saving.

“Well, it is the Sun-Times—a major metropolitan newspaper in our town,” Canning remembers thinking.

He agreed, with one caveat: They needed “to find a Tyree kind of guy, ’cause I’m not going to spend any time on this.” Hence Canning’s fateful summer 2011 call to Ferro.

The younger man’s first reaction was no. “I don’t know anything about the newspaper business,” Ferro says he told his friend. “I like to be in businesses that I know something about.”

But the more Ferro thought about it, the more intrigued he became with what he saw as parallels between the worlds of software and journalism. “Programmers and journalists are very similar,” Ferro explains. “They all like to do their own thing, they want to build their own product, they’re all very opinionated, and they’re very intelligent.

“So I came up with this idea. I said, I believe there’s a way to use these traditional print assets to build new digital properties, and leverage the distribution and the eyeballs, the readership, to launch those properties.”

Tapping their network of powerful Chicagoans, Canning and Ferro put together an investor group that would be dubbed Wrapports. The name signifies a merging of the “wrap” of a traditional print publication with the “ports” of tech ventures, Ferro explains.

Initially, Ferro kicked in about $10 million; Canning, $5 million. The other investors put in smaller amounts. “Nobody [else] contributed more than $4.7 million,” Canning says.

In December 2011, they negotiated a purchase price of about $20 million for Sun-Times Media, which owned not only the money-losing namesake paper but also seven suburban dailies and the Pioneer Press chain of 32 suburban weeklies. That Ferro became chairman, Canning says, “was kind of a precondition to doing the deal.”

As time went on, the investments increased. Sources close to Wrapports estimate that to date the team has spent $60 million, in part to pay for new launches and to keep the business afloat as it works toward profitability.

Even the most old-school Sun-Timesers realize that newspapers are fighting for their lives. Consumers continue to abandon print in droves. Meanwhile, advertisers pay far less for ads on newspapers’ websites or digital editions than they once paid for them in print. What about digital paywalls? Sure, they collect money from readers, but they typically lower traffic, which in turn hurts ad revenues. In short, newspapers today are dicey investments. So why are so many rich people buying them?

For one thing, their value has plummeted so dramatically that they can be had for a song—from a mogul’s perspective, anyway. Warren Buffett’s Berkshire Hathaway has shelled out $344 million over the past two years to buy 28 mostly small-market newspapers. That price is practically a rounding error for a man whose net worth is pegged by Forbes at more than $58 billion.

Today you don’t even have to be particularly rich to own a big-city paper. At $20 million, Sun-Times Media “cost less than Michael Jordan asked for his house when he first listed it,” points out Mike Conklin, a former writer and editor at the Tribune who now teaches journalism and media at DePaul University.

Despite the industry’s struggles, there’s still cachet to owning a major newspaper, observes Marshall Sonenshine, an investment banker who runs Sonenshine Partners in New York City. “You can be a civic leader by owning a newspaper,” he says, “just like you can be a civic leader by putting $100 million into the public library.”

Don’t forget the ego factor, says Ken Doctor, a media analyst at research firm Outsell in Burlingame, California. “Vanity looms large in all of these things. … In almost every case, there’s an element of, ‘I’m smarter than everyone else.’ It’s an extreme confidence, bordering on arrogance, that maybe those other guys couldn’t figure it out, but I can. I have the business acumen to figure out how to turn this around.”

I ask Ferro, Canning, and Wrapports partner William “Beau” Wrigley Jr., the former CEO of the candy company that bears his family’s name, about their motivation. (None of the other major Wrapports investors except Joe Mansueto, the founder and CEO of financial information giant Morningstar, responded to interview requests.) All three somewhat dutifully mention the important role that a vigorous press plays in a democracy. Civic pride factors in, too: If Chicago is truly a world-class city, shouldn’t it be able to sustain more than one major daily?

In Ferro, media observers also recognize the ego that Doctor alluded to. “It’s clear that [Ferro] sees himself as some sort of visionary genius up there with Jeff Bezos and Mark Zuckerberg,” says Feder. “To me, it seems he just saw [the paper] as a platform for his gigantic ego and an incubator for his pet projects.”

Others see in the deal something more personal: That perhaps this was Ferro’s chance to show Chicago, and the world, that he wasn’t just a one-hit wonder. That the score he made with Click Commerce was more than just a lucky break. What better way than to find a solution to a problem that has perplexed just about everyone: How do you take a newspaper in the 2010s and make it thrive?

Ferro had a tough act to follow. James Tyree was widely respected in the newsroom—remarkable given that he eliminated the company’s traditional pension plan and froze salaries for three years as a precondition for buying the paper in 2009. (Tyree died in March 2011 at age 53 from an air embolism following the incorrect removal of a catheter at the University of Chicago Medical Center.)

He didn’t meddle in editorial decisions, current and former Sun-Times employees say. He trod lightly on turf with which he knew he was unfamiliar. Tyree won the rank and file’s fealty the old-fashioned way: by treating them with respect, by honoring their craft in word and in deed, and by simply being friendly.

“Jim Tyree was the real deal,” says Feder. “He never saw the Sun-Times as a steppingstone to greater glory. The guy wasn’t perfect, but there was never any doubt his heart was in the right place. All he wanted was to put the paper on sound financial footing and keep it going.

“With Ferro, on the other hand, it was clear from the start he had something else in mind. He showed no respect for the heritage or the legacy of the organization. I don’t think he gave a rat’s ass about the Sun-Times as a newspaper.”

Exhibit A, say dozens of former and current staffers: Ferro’s first speech to employees. It happened on a late morning in early January of last year, a few weeks after Wrapports had officially taken control of Sun-Times Media.

The assembled group of grizzled reporters, editors, photographers, business-side staffers, and managers were intensely curious about their company’s new owner. They knew little about him beyond the fact that he had the trust of some of Chicago’s most respected businessmen. And they knew that he had ridden to the rescue when no one else seemed interested in buying the paper and the other print assets from Tyree’s estate. That was cause for gratitude no matter who he turned out to be.

Ferro strode into the room with his new right-hand man, Wrapports CEO Timothy Knight. (Knight says, “Michael was very enthusiastic about the business and cultural changes he planned to enact.”) What followed was pure Ferro. Upbeat, almost giddy, he unleashed a stream-of-consciousness torrent of dramatic ideas and projections, a mix of bombast, braggadocio, and bravado. “The only way to describe it is like when a kid gets a new toy,” recalls a reporter who left shortly after Ferro took over.

“He talked about building a candy room and a cereal room and walk-around desks he planned to install,” adds another former staffer. “There was going to be a game room, and we were all going to get lanyards with name tags, and he was going to change the color of the walls. He hated the white walls.” For some, the energy was infectious. (“We’re going to get candy!” one person stage-whispered.) “There seemed to be hope,” another recalls, “or at least the benefit of the doubt.”

For others, the speech was disconcerting. Some found it graceless that Ferro did not acknowledge the heavy lifting that then publisher John Barron and editor in chief Don Hayner had done to keep the paper afloat after Tyree’s death. Some were dismayed to learn how little Ferro knew about the media in general and the Sun-Times in particular. (Among his first words was an admission that he didn’t really read the Sun-Times and that he had to be talked into becoming its chairman.)

But the biggest problem for many was Ferro’s tone. “I was thinking, Do you not understand that you have a completely dispirited, nervous newsroom on your hands?” a former staffer recalls. “We had been through so much. So many of our friends had been laid off. We were afraid, and he’s walking around talking about colored walls and a cereal room?”

What followed was a rapid series of moves, many of which have been viewed as either PR fiascoes or flat-out broadsides against anything resembling traditional journalism.

Less than a month after Ferro arrived, for example, came the decision to end the Sun-Times’ 71-year-old tradition of endorsing political candidates—a tradition that is widely considered essential to the mission of a city newspaper. “We have come to doubt the value of candidate endorsements by this newspaper or any newspaper, especially in a day when a multitude of information sources allow even a casual voter to be better informed than ever before,” the paper said at the time. The move was stunning enough to attract coverage in national media, including The New York Times.

Then there was Ferro’s personally signing as columnists several celebrities with zero journalism experience, including Jim Belushi and Jenny McCarthy. “They drive traffic,” Ferro says unapologetically. “Jenny is our No. 1 driver of traffic digitally to Splash. No. 1. And she’s prolific. Do I read Jenny every day? I do not. She’s quizzed me on this. But I’m not her target audience. Jenny does not write for men.” (With McCarthy’s recent hiring as a host of the ABC talk show The View—a gig that Ferro insists she got largely because of her column—it was unclear at presstime how much longer she’d be penning it.)

Last year, five days before Christmas, Kirk announced that the Sun-Times would shutter its six suburban bureaus in early 2013. Fifteen editors and members of the production staff would be laid off. Kirk’s memo cited the need to “shed inefficiencies” and become “more nimble on the reporting front.” Journalists were instructed to cover their beats from their home offices or cars.

In February came the decision to kill the Sun-Times’ business section, replacing it with Chicago Grid, a sassy new Sunday business magazine (tag line: “All Up in Your Business”). Kirk told the paper’s three business reporters, David Roeder, Sandra Guy, and Francine Knowles, that they would now be working for the new publication.

Grid, like all the ventures that the company has launched in the Ferro era, is staffed with nonunion employees. After the Newspaper Guild filed charges of unfair labor practices, the three reporters found themselves back at the Sun-Times but relegated to less prestigious general assignment beats. Roeder announced in early October that he was leaving the paper after 17 years to join the administration of Governor Pat Quinn. The Sun-Times business section never returned.

Meanwhile, Ferro admits that Grid’s print and digital editions have attracted neither the eyeballs nor the advertising dollars that he’d hoped. Within four months, the weekly print publication was placed on hiatus (it returned as a monthly in June). In October, the paper decided to kill the print version of Grid altogether. The section continues to provide digital content for the Sun-Times website.

Another major flap involved the Sun-Times’ November 2012 obituary of David Speer, CEO of Illinois Tool Works (the company that had purchased Click Commerce) and a mentor of Ferro’s. The obit consumed the entire front page and two inside pages, a highly unusual decision. It was reportedly made by Ferro himself. (Kirk says it was a legitimate editorial decision.) “It was a flagrant abuse of his power as publisher and yet another example of Ferro’s ego undermining the credibility of the paper,” fumed Feder, writing for Time Out Chicago at the time. “Hiring wannabe columnist Jenny McCarthy was merely foolish. But dictating the news cover is shameful and disgusting.”

“Let’s talk about that,” Ferro responds, his voice rising. “David Speer was chair of the United Way, the Economic Club; he ran a Fortune 150 company. When [McDonald’s founder] Ray Kroc died, the Tribune had it on its cover. This was a young guy in his 50s who was one of the largest employers in the city of Chicago.” [In fact, the obituary ran on page 5 of the business section, and Speer was 61.] “And by the way,” Ferro continues, “it was one of the best things we ever did. People read the Sun-Times because of that. I probably have had a thousand good comments. Zero negativity from anybody on the street.”

Longtime media critic Michael Miner, who as a Reader employee works for Ferro, says that he had no problem with the Speer obituary. Ferro “is certainly not the first rich guy who ran a newspaper to stick [something] on the front page that nobody else could believe [he put there],” Miner says. “That’s his right. He writes the checks.”

Miner feels differently, however, about the paper eliminating its entire 29-member photography staff in June, instead relying on reporters to shoot pictures with their smartphones. “I don’t see how he can say it’s a good thing,” Miner says. “It’s not a good thing. It maims the paper. It maims the paper’s sense of self.”

Ironically, Ferro insists that he loves photography. On our tour, he grows particularly animated as he proudly points out framed photos hanging on the walls of the 10th floor and in his office: “They’re all by Sun-Times photographers.”

I barely begin to ask the obvious question before he jumps in. “I know what you’re going to say,” he says. “But the world has changed. I mean, this took a lot of work back then. A guy had to develop the film. It could take days to get this shot. Now we have thousands of photos to select from. So when Jim [Kirk] wants to pull a photo of Jay Cutler jumping up and down, he has a thousand choices.

“It’s also a multimedia world,” Ferro continues. “A world of Snapchat and editing on the fly. You’ve got to be able to take video and put it out there. You just gotta go, go with it and clean it all up after.

“I am very sympathetic toward [the photographers]. If I were in their shoes, I would feel bad too. It would be like you’re a carriage driver and the cars come and you’re really upset that you can’t have your buggy whip and hit your horse anymore.”

In fact, Ferro says, the photographers should have been let go sooner. “I knew the photographers would be going from the day we took this paper over. We took a year and a half too long to do it. … I can tell you 100 percent before we bought this we had that cutlass ready.”

Given such tact-challenged statements, it’s little wonder that “demoralized,” “depressed,” and “disrespected” are the words I hear most from Sun-Times staffers to describe the mood in the newsroom. They’ve been working without a union contract for months. They feel almost mocked by the shiny new game room that most of them are too overworked to frequent. Why wasn’t the money spent on Pleasure Island (as some call the candy room) used for raises, considering that salaries have been frozen since 2009? Some union members openly wear stickers on their shirts that read “Un-Ferro”—as in “Unfair-o.”

However, when I head to the ninth floor to visit Mara Shalhoup, the editor in chief of the Reader since early 2011, she seems utterly at peace with Wrapports’s purchase of the still-profitable 42-year-old alt-weekly. When asked what Ferro is like to work with, she says: “I’m probably not the person who has dealt with him in that way often enough to speak terribly intelligently on that.”

Morale also seems just fine at Splash, the year-old Ferro brainchild edited by Susanna Negovan (former editor of Michigan Avenue magazine). She says the publication is attracting advertisers that have typically shunned the Sun-Times, including Neiman Marcus and Waldorf Astoria Chicago. After showing me her windowless hot-pink office, Negovan lavishes praise on Ferro, saying that he has been involved in everything from prototypes to cover choices.

“He’s been a really incredible boss,” Negovan says. “Anytime I ask him for an opinion, he has an opinion. … He was coming to this industry with no preconceived notions. He didn’t know what couldn’t be done.” She adds that she considers Ferro “one of the most fearless people I’ve worked for.”

Kirk also counts himself a supporter: “The great thing about working for [Ferro] is that he will throw at you 20 ideas in a day. Eighteen of them sound absurd, but there’s something to three of them as you kind of mull it over. You just have to try to figure out, Does it make sense to go down this path?

“The important thing is we’re experimenting the whole time,” Kirk continues. “Not everything’s going to work. But we are experimenting more than any other big-city newspaper right now. It’s a tough time, but it’s a business model that’s broken.”

I even get something of an endorsement from Sun-Times columnist Neil Steinberg, who has felt the sting of changes since Ferro took over—namely having his column reduced to once a week and relegated to the back of the paper. “We’ve been owned by some world-class idiots, and he’s not one of them,” says Steinberg. “Does he have the best bedside manner? No. He’s a multimillionaire, and he can be very abrupt. … But I think Michael Ferro has a vision. I think he’s taking us somewhere. Now whether you like where he’s taking you is a different matter.”

Ferro declared at a speech before the U.S. Conference of Mayors in March 2012 that “my plan is to acquire [your] publications in a lot of [your] cities today and keep newspapers alive in America.”

Like many of Ferro’s grand plans, this one hasn’t materialized. When it comes to the Sun-Times, he seems to value the paper mainly for its ability to help launch new digital ventures. Pressed further, he explains that if one of the new ventures “hits and hits hard,” there will be plenty of money both to repay investors and to keep the Sun-Times in business—in digital form, at least.

“The problem with new ideas is that most of them don’t work,” Ferro says. “This is one of the problems Chicago has, which is why we will never be a tech city. People don’t understand that you need to do 10 ideas and try them out and have one work. So as I try all these new products—most of them need to fail to have one succeed. That is not dysfunctional.”

One of the new ventures for which Ferro has high hopes is Aggrego, a provider of low-cost hyperlocal content run by Tim Landon, former head of Tribune Interactive. With the help of special software, employees comb a myriad of sources, including Sun-Times Media stories, third-party content providers, and the Internet, collecting and slotting stories and information into “channels” such as news, sports, and weddings. So far Aggrego’s content appears only in the Pioneer Press weeklies and the Sun-Times-owned suburban newspapers, but Ferro aims to expand to communities around the country.

Another favorite is High School Cube, a platform that lets high-school teachers, coaches, parents, and students broadcast live video of their sports events, academic competitions, and artistic performances from a variety of devices. It was founded by Larry Cotter and Kevin Doyle, who had previously launched Apartments.com; Wrapports bought 40 percent of the company in May 2012. High School Cube, which Cotter says is now in 1,800 schools in 46 states and in several countries, “has the ability to be bought for billions by a Facebook next year or become the ESPN of high-school sports,” says Ferro enthusiastically. “They’re that much on fire.”

Wrapports also bought the domain name Chicago.com recently. Ferro envisions turning it into the go-to Chicago commerce and content site: part Facebook, part Groupon, part ticket broker, part e–shopping mall. Subscribers will get access to all of those things, as well as to an @chicago.com e-mail address, Ferro says. They’ll also get a subscription to the Sun-Times.

While Ferro may sincerely believe he has found a game-changing approach, media analysts are skeptical. His strategy “makes sense in the abstract,” says Doctor. “Yet newspapers in Boston, San Francisco, and Houston each have powerful city sites and haven’t been able to translate those to substantial commercial success.”

One big unknown, of course, is how much money it will take to keep the still-unprofitable company afloat until one of the digital ventures “hits.” Ferro himself seems almost shocked at how much his team has had to shell out beyond the initial purchase price. “No one understands how much money has gone into this,” he says. “You can more than double the number that people think and you still wouldn’t be there.”

Unfortunately, the number of people who read the Sun-Times continues to dwindle. According to the Alliance for Audited Media, the paper’s average weekday print circulation fell nearly 8 percent (to 185,000) over the six months ending March 31, compared with the same period in the previous year. By contrast, the Tribune and The Wall Street Journal saw losses of 5 percent; The New York Times, 6 percent. More troubling is that while the number of digital subscriptions for those three papers rocketed from 41 to 71 percent in the period, the Sun-Times managed only a 13 percent increase.

On the plus side, in May, Sun-Times Media gave required advance notice that it would cancel long-term printing and distribution contracts with Tribune that were costing the “onerous” sum of about $70 million per year, says Canning. That move will free the company to find a cheaper printing alternative in May 2015—or even, some speculate, to exit print altogether. (While he didn’t comment on that specifically, Ferro does say, “Everything has to become digital. … Because you can’t make money on traditional print.”)

So far, at least, the Wrapports investors who spoke to me don’t seem bothered by the company’s performance. “There’s still work to be done,” says Mansueto. “[But] the point is, we’re still in the middle of the story. … I like Michael and I support him.”

Says Wrigley: “I don’t think anyone going into this thought it was going to be some sort of a home run, a 10-times-your-investment kind of a thing. Any business is a risk. But there’s tons of staying power. That’s not a concern.”

Ferro himself says that he’s in for the long haul. When I ask if that means years, he says, “I’ve put the money and the time into this. There’s really nowhere for me to go.”

The tour is nearly over. With each section of the building that he shows me, Ferro’s enthusiasm seems to wane a little. Despite his promises on that January day, the Sun-Times newsroom is neither colorful nor fun. The biggest change was to rip out the existing cubicles, relatively spacious ones that had given reporters a bit of storage and a modicum of privacy to make sensitive phone calls. To accommodate an influx of reporters who moved to the building when the paper closed its suburban offices, more desks were brought in, packed so tightly that one staffer describes the place as looking like a telemarketing call center.

As Ferro, the PR representative, Kirk, and I walk through the newsroom, not a single reporter looks up or even seems to notice us. “This ugly room has been here forever,” Ferro says, gesturing. (“That’s our editorial board room,” Kirk tells me sotto voce.)

We stop briefly by Neil Steinberg’s cluttered office. “Look, Neil’s recycling,” says Ferro somewhat randomly.

“Fun assignment you pulled,” Steinberg says to me.

When the tour reaches the finance department, a small, drab corner on the newsroom floor, Ferro seems dismissive. “I don’t really pay attention to it,” he says, adding, “These are the people who are actually supposedly paying our bills.”

With that, he starts to lead me out, then pauses for a moment, looking slightly lost. He turns to Kirk.

“How do you get back out of here, Jim?”