Dean Singleton: A Man Accustomed to Getting What He Wants

Dean Singleton: A Man Accustomed to Getting What He Wants

By Scott Sherman and Michael Roberts,

Newspaper baron Dean Singleton prides himself on straight talk. Ask him about flying, however, and his first claim—”I don’t know beans about airplanes”—is, at best, a half-truth.

MediaNews has procured five jets during the past two decades. The fourth was this Westwind II, seen behind CEO Dean Singleton. Singleton, who now utilizes a Dassault Falcon 2000, says a plane is “just a tool, like a printing press.”

MediaNews has procured five jets during the past two decades. The fourth was this Westwind II, seen behind CEO Dean Singleton. Singleton, who now utilizes a Dassault Falcon 2000, says a plane is “just a tool, like a printing press.”

Granted, Singleton, the 54-year-old chief executive officer of Denver-based MediaNews Group, isn’t a pilot, and he has little more than a rudimentary understanding of aerodynamics and technical minutiae. In his opinion, “A plane is just a tool, like a printing press.” But he has no trouble rattling off the names and models of the five jets MediaNews has procured during the past two decades. And thanks to a months-long analysis that preceded his decision to trade in MediaNews’ previous craft, a Westwind II, for a Dassault Falcon 2000, he’s got a firm grasp on the details that matter most to him: size, speed and, most of all, economy.

“We were looking for a plane that was roomy, because sometimes we take large groups with us, and we were looking for one that we’d never have to stop for fuel,” he says. “Not only did the Falcon have the range and comfort we were looking for, but it was, by far, the lowest-cost plane to operate in its class. In fact, the total operating costs were less than they were for the Westwind II, and that’s a much smaller airplane, with a lot less range and comfort. So it was a plane that fit our needs and was very efficient.” He chuckles as he adds, “That’s probably a nice word for ‘cheap.'”

This last term is one with which Singleton is intimately familiar—and he’s certainly heard worse. His reputation for penny-pinching and job-slashing led Editor & Publisher to dub him “Lean Dean,” while the New York Times once referred to him as “the industry’s leading skinflint.” As for James Squires, a former editor at the Chicago Tribune, he called Singleton “a bone-picker publisher . who can wring blood from a turnip.”

In recent years, the name-calling directed at Singleton has gotten less vituperative as he’s grown more successful. Today, the MediaNews empire consists of 40 daily newspapers and a gaggle of non-dailies, plus a handful of radio stations in Texas and a TV station in Alaska—and the venture is in the midst of a major growth spurt. In April, MediaNews, in association with Hearst Corp., bought the San Jose Mercury News and three other daily newspapers from the McClatchy Co., which had obtained the properties through its acquisition of another print giant, Knight Ridder Inc. The reported price tag for the publications was $1 billion, with MediaNews’ share coming in at just over $736 million. Thanks to the transaction, MediaNews is now the fourth largest U.S. newspaper company as judged by circulation (up from seventh place), and the undisputed newspaper champ in California, one of 11 states where the firm operates.

Nevertheless, Singleton remains as thrifty as ever—and his purchase of the Falcon is a case in point. The past MediaNews planes were used when Singleton picked them up, and while he can certainly afford a new jet these days, he went hunting for a bargain anyway. And he found one.

“The plane was owned by a medical supply company in Florida; it was used, but only slightly,” he says. “We got a really good deal.”

Described as someone with “instinctiveness about people and business,” Dean Singleton is the CEO of Denver-based MediaNews Group, the fourth largest U.S. newspaper company. The empire presently consists of 40 daily newspapers and a gaggle of non-dailies.

Described as someone with “instinctiveness about people and business,” Dean Singleton is the CEO of Denver-based MediaNews Group, the fourth largest U.S. newspaper company. The empire presently consists of 40 daily newspapers and a gaggle of non-dailies.

Dean Singleton’s extraordinary business savvy has made him a full-fledged member of the American elite. He cavorts with presidents and senators and is a leading member of Denver society. His primary residence, where he lives with his wife, Adrienne, and three children, is a stunning mansion in Denver’s wealthiest neighborhood—a mansion that contains 11 bathrooms and an elevator, since he has difficulty climbing stairs due to multiple sclerosis, which was diagnosed in 1986. But even though he says his legs get progressively weaker each year, he remains extraordinarily active. He owns four cattle ranches in Colorado, along with a home on Cape Cod where, during the summer months, he goes sailing with the musician James Taylor.

Appearances aside, Singleton wasn’t born to wealth; he didn’t inherit his newspapers. He came of age in Graham, Texas, a community 90 miles west of Forth Worth that’s surrounded by oil fields and ranchland in every direction. It’s a super-conservative, super-religious place, mostly white, with more than 50 churches serving a population of 9,000. Singleton will be buried here, alongside his parents, in a small cemetery on the outskirts of town.

For much of his youth, he lived in a ramshackle four-room house on Pecan Street, in a grim section of Graham. His father toiled as a day laborer in the oil fields—a “roustabout” in Texas lingo—but frequently there was no work, so he came home early.

“We didn’t have anything,” Singleton says.

At night he would lie in bed with a transistor radio, and, as a result of clear channel signals, would pick up stations from New York and Oklahoma City, which instilled in him a sense of the larger world. At the age of 6, he would walk a few blocks to the 4,000-circulation Graham Leader and watch the papers roll off the presses; sometimes the pressmen bought him ice cream. By age 18, he had been a sportswriter for both the Leader and its cross-town competitor, the News. (Many years later, in 1986, Singleton purchased the Graham Leader, and he takes an active interest in its affairs.)

After a series of small-town newspaper jobs in Texas, Singleton landed at the Dallas Morning News in 1970, and worked in the newsroom at night while attending the University of Texas at Arlington by day. But he already knew that he wanted his own newspapers, so he quit school and moved to a small town in the Texas Panhandle, Clarendon, where he bought a tiny weekly. He never finished college, and has no degree.

“He’s not well read,” says David Burgin, who, over the years, was fired and rehired on several occasions by Singleton, and who knows him as well as anyone. “He doesn’t sit down with a new book three times a week. He doesn’t spend his time in the movies or the theater. He doesn’t get lost in the opera or the arts. He’s not particularly well-educated. But he has an instinctiveness about people and business.”

By 1975, Singleton was the owner of eight small weeklies in West Texas, but he was “getting itchy.” So he set his sights on the Fort Worth Press, which Scripps Howard wanted to unload. Singleton, with borrowed money, rolled into Fort Worth with a new Lincoln Continental, and tried to revive the paper.

“I don’t think it is too much to ask for five or more stories out of each reporter each day,” he wrote in a memo to the staff. But reporters were expected to do more than write; they had to shop, too. As Singleton wrote in another memo: “On page 5 of today’s Press, you will find an ad from Mitchell’s Department Store. … Mitchell’s is comparing our results with the morning Star-Telegram’s. … If we make a good showing we will have a regular schedule of advertising from Mitchell’s. If they don’t receive many coupons, we likely won’t get their advertising. In a sense, YOUR JOBS DEPEND ON THE NUMBER OF COUPONS MITCHELL’S GETS FROM THIS ADVERTISEMENT. Please get your wives to look at this ad, decide what items you can use from this ad and TAKE THE COUPONS to a nearby Mitchell’s store. … I’ll see you at Mitchell’s today!!!”

The newspaper folded after 88 days.

“It was a total disaster,” says Singleton. “I knew nothing about the business of newspapering.” He lost a million dollars in the demise of the Fort Worth Press, and he had to sell his weeklies to pay his debts. The experience put him in the hospital for depression and exhaustion.

“In 12 weeks it closed, and he lost his ass,” says David Burgin. “Poor Dean kicked around and couldn’t find anything. And he was only 24 years old.”

In August 1976, Singleton found himself in the executive dining room of the Washington Star, face to face with the Star’s owner, Joe L. Allbritton, whose background bore some resemblance to Singleton’s. Born in D’Lo, Miss., during the Great Depression, Allbritton spent his early years in Texas, acquired banks, real estate, and even funeral homes—some Star reporters called him “the little mortician”—and purchased Washington’s second newspaper in 1974.

Over lunch, Singleton informed Allbritton of his plan to buy a small daily in Westfield, Mass., the Westfield Evening News. Might he be interested in putting up the money for it? Allbritton, as Singleton tells the story, wasn’t interested.

“Joe had decided I was too young, and he didn’t really know if he wanted this little paper anyway,” Singleton said. Allbritton said goodbye and good luck. “I got up and pushed my coat back, and he saw I had suspenders,” Singleton recalls. “I was walking out the door and he said, ‘Young man! Young man! Will you come back here?’ He said, ‘Any 25-year-old who wears suspenders has got to be conservative. You go up there and buy the newspaper and I’ll wire ’em the money.'”

In short order, Allbritton purchased a number of papers for Singleton to run, mostly in New Jersey. The papers were floundering, and had to be, to use a favorite phrase of Singleton’s, “turned around.” It was Singleton’s view that cost-cutting—combined with a relentless emphasis on local news—was the way to proceed; his editors didn’t always agree. In 1976, when Singleton moved to Westfield to publish the Evening News, he asked David Burgin, then editing Allbritton’s paper in Paterson, to come to Massachusetts as the temporary editor. Burgin was less than thrilled with the assignment, for he was on a downward trajectory within Allbritton’s media empire.

“Jesus,” he recalls, “just a year ago I was working at the Washington Star, trying to bring down the president, and look at me now!”

Burgin knew that some readers would be interested in the Camp David peace talks then under way between Jimmy Carter, Menachem Begin, and Anwar Sadat. On the day they reached the accord, Burgin, laying out the front page, made Camp David the top story. Singleton came in and peered over his shoulder.

“Damn it!” Singleton shouted in his thick drawl. “This is a local paper! We don’t sell no fucking papers in Cairo! Get that thing off there, right now!”

“Get your sorry ass out of here!” Burgin replied, as he recalls it. “I’m the editor of this newspaper!”

Singleton fired him on the spot, but Burgin stuck around to close the evening edition. At the time, Burgin was staying with Singleton at a nearby house. Still smoldering, Burgin drove there later and saw Singleton’s car in the driveway. Burgin heard a splash.

“There was a pool, and there’s Dean about chest deep in the shallow end,” he recalled. “He looks at me for about 30 seconds.”

“I told you you’re fired!” Singleton roared.

“Sitting beside the pool was a contraption, a cage,” Burgin said. “Inside there’s a strange looking bulb, a blue light. It was a bug zapper. It’s plugged in by the pool. I looked at that bug zapper and I looked at Dean. I looked at the bug zapper and I looked back at Dean. After about three of those he said, ‘No, no, no!’ He thinks I’m going to kick it in the pool and he’ll be a slice of bacon floating on the top of the pool. He says, ‘That would be murder!’ I said, ‘who’s gonna know, asshole?’ He took about point eight seconds to get out of the pool.”

Burgin was back at work the next day.

Working for Allbritton could be stressful. In 1981, Singleton found himself enmeshed in a labor dispute at the Paterson News, where the unionized typographers and drivers were restive. In the course of the strike, the workers were swiftly vanquished.

“We were losing money and had to fix it, so we took on the unions and threw ’em out,” Singleton recalls. The strike got ugly, and for six months Singleton lived in a spare room inside the newspaper. “I told them if they walked out that I’d never let them back,” he says. “They walked out and they never came back.” Asked if he has any regrets, Singleton grins. “No. When they left, we started making money.”

In the late 1970s, much of the industry was watching the heated newspaper war in New Jersey between the Trenton Times— owned by the Washington Post Company—and a tabloid competitor, the Trentonian. In the mid-1970s, Katharine Graham had decided that she wanted to transform the Times into a first-rate newspaper, and sent some top editors to Trenton to remake it. But Trenton residents didn’t necessarily want a smaller version of the Washington Post; many of them preferred the localized news of the Trentonian, which stuffed its pages with cheerful photographs of local residents. Big profits at the Times never materialized, and Kay Graham eventually came to see the acquisition as her “Vietnam.”

Singleton reveals that Kay Graham asked him to take over the Trenton Times and stem the losses. He had become friendly with Donald Graham in 1977, and when Allbritton asked Singleton to run the beleaguered Star for a year—a year in which the paper turned an operating profit—the Grahams had been impressed.

“Kay Graham, in 1980, offered me the job to come run it,” Singleton says of the Trenton Times. “She offered me the publisher’s job and 20 percent of the stock.” That was in a new company that would also buy other newspapers.

But Singleton says he felt enormous loyalty to Allbritton, and a certain reluctance to go work for his primary competitor—Kay Graham.

“Joe picked me up when I was down,” he said. “I had just lost my ass in Fort Worth, and Joe gave me my second chance.” Singleton turned down the offer.

He claims he then got a call from Kay Graham, who said, “If you won’t go and run it for me, buy the thing.” So he and Allbritton did.

“The Washington Post basically gave it to us,” Singleton says. Two days after the purchase, Singleton fired 60 Trenton Times staff members. In the subsequent months, as reporters fled, many observers insisted that a great newspaper was being dismantled. In one notorious instance, a cub reporter was fired for adding a handful of relevant details to a press release about a department store closing. (He had been instructed to run the press release word for word.) The Philadelphia Inquirer reported that, in at least one instance, the Trenton Times had published a news story in exchange for an advertisement.

In 1986, Allbritton sold the paper to Newhouse for a rumored $62 million. Singleton notes with satisfaction and defiance, “We saved the Trenton Times and made it dominant.”

Eventually, Singleton grew weary of working for Allbritton—especially since Allbritton declined to make him a partner.

“Joe Allbritton never has partners,” Singleton grumbled to the New York Times in 1987. So Singleton looked elsewhere for opportunities. In the late 1970s, he became friendly with one of his creditors—Richard Scudder, chairman of the Garden State Paper Company, New Jersey’s only manufacturer of newsprint. (In fact, Scudder himself invented the technology behind recycled newsprint.) In 1983, Singleton informed Allbritton he was launching a newspaper company, later to be called MediaNews, with Scudder.

Together, Singleton and Scudder purchased newspapers in Massachusetts, Ohio, New Jersey and California. Their first metro acquisition—from Times Mirror—was the Dallas Times Herald, the city’s number two daily. The Times Herald was far from healthy: the year Singleton bought it, it lost $9 million. Times Mirror was relieved to unburden itself of the paper; it had never found a way to make the Times Herald work. For their part, reporters—recalling the evisceration of the Trenton Times— responded to the news of the sale with trepidation. The Boston Globe reported in 1987 that Singleton’s arrival in Dallas “caused near pandemonium in the newsroom.”

The Times Herald was Singleton’s first purchase of a major newspaper, and it was something of a milestone for him—his arrival in the big leagues. For Dean Singleton, being a cost-conscious boy publisher was never easy. He had trouble socializing with reporters and editors, some of whom made fun of him behind his back, ridiculing his noticeable lisp. After the press conference announcing the purchase of the Times Herald, David Burgin, who was to edit the paper, walked out to get his car, and found Singleton alone by the loading docks.

“He was standing there, just looking,” Burgin said. He asked Singleton if he was OK.

“Yeah,” Singleton replied. “I just spent $120 million dollars, and I never spent $120 million dollars before.”

Burgin remembers, “He turned around and there were tears coming down his eyes. He was lost. He’d just done this incredible thing. He didn’t have anywhere to go. He didn’t have anybody to have dinner with. What are you going to do, go back to the hotel room and watch TV after spending $120 million dollars? He needed attention. I gave it to him.” They drank $12 shots of brandy at a fine hotel bar.

But the purchase turned out to be a mistake. Singleton says the Times Herald “was a blue-collar paper in a white-collar market” with a weak Sunday edition. And it came out in the afternoon, while the heavyweight establishment News ruled the morning. On top of that, the Texas economy was in terrible shape.

“You could just see the trend line,” he says, “and it wasn’t good. I bought it out of emotion. It’s 120 miles from where I was born, a paper I grew up admiring and respecting.” After 18 months, he sold the Times Herald to an associate, who closed it. Singleton still walked away with $15 million from the sale.

In September 1987, he stunned the newspaper world by announcing two major acquisitions—the Houston Post and the Denver Post. Houston was the reverse of Dallas, Singleton says, “a white-collar paper in a blue-collar market,” but the Sunday edition was similarly weak.

Eight years later, in 1995, Singleton sold the assets of the Houston Post to its main competitor, Hearst, publisher of the dominant Houston Chronicle, for $120 million. The Houston Post was a corpse. Employees of that publication were enraged, and have remained so ever since; today they refer to him as “Stinky Singleton.”

Writing in the Houston Press, an alternative weekly, Tim Fleck and Jim Simmon revealed in 1995 that Singleton had secretly reached an agreement with Hearst eight months before the Houston Post was shuttered, but went through the motions of publicly seeking a buyer to gain the nod of the Justice Department, which might have objected on antitrust grounds. Singleton doesn’t dispute the Houston Press account, but he maintains that he offered the Houston Post to 48 buyers, and that one of them, the Belo Corporation, offered $70 million, $50 million less than Hearst, but the deal fell through.

Buying the Houston Post was another mistake, Singleton admits, but he claims he prolonged the newspaper’s life. He says, “It would have died right away,” in 1987, if he hadn’t bought it. “I gave it seven years it wouldn’t have had.” Certainly, the Houston Post’s editorial side had been weakened by its previous owners, and with or without Singleton, it had enormous woes.

From the start, MediaNews focused much of its energy on California. In 1985, Singleton purchased a group of dailies in the fast-growing suburbs around San Francisco; then, in 1992, he bought the Oakland Tribune, which was losing about $1 million a month. The paper had been a beacon for African-American journalists as the only major paper with a black owner (the late Robert Maynard). But Singleton didn’t buy it for sentimental reasons; he controlled the market in Alameda County, of which Oakland is the county and cultural seat. If the Oakland Tribune had folded, Singleton explains, “The San Francisco Chronicle would have picked up most of the circulation, and we would have invited a new competitor into our market. We couldn’t let that happen.” (By reducing the staff from 630 to 280, Singleton eventually made the Oakland Tribune profitable.)

For years his Northern California papers pooled their resources—they even had a centralized copy-editing center for all the publications. In recent years, they’ve pulled back from that strategy, giving more autonomy to the individual papers, but from an advertising perspective, this “clustering” has paid off handsomely. Individually, his papers couldn’t attract national and large department store advertising. Jointly, they could—and their circulation figures will get a major boost from three of his recent purchases, most notably the San Jose Mercury News.

In the mid-1990s, Singleton made a major push into Southern California as well, again following the “clustering” strategy, buying half a dozen papers, most notably the Los Angeles Daily News. These acquisitions gave Singleton control over a huge swath of suburban Los Angeles. He was eager to keep expanding, and in 1997 he made an offer for the Inland Valley Daily Bulletin, located in a fast-growing suburban zone. When the owners, the Stephens Media Group, declined his request, Singleton came back with a proposal that revealed the full range of his business acumen. Could MediaNews and Stephens, he suggested, combine their papers in a partnership, and divide the profits accordingly? Stephens found the offer attractive (largely for tax reasons) and agreed to contribute 12 dailies to the consortium. Thus was born the California Newspaper Partnership, which also includes Gannett, which added two papers.

Nothing is more illustrative of Singleton’s business acumen than his unpublicized deal with Times Mirror, the owner of the Los Angeles Times, concerning the Los Angeles Daily News. In 1997 the Daily News went up for sale, and Singleton was eager to purchase it. But he had some concerns.

“We were a little reluctant to get into a head-to-head battle with Times Mirror,” he said. “They were very good friends.”

For antitrust reasons, Times Mirror couldn’t purchase the Daily News, and it was concerned about who might; its executives didn’t want a fierce competitor—like Rupert Murdoch—in their core market. A creative solution was found: Times Mirror lent Singleton $50 million of the $130 million purchase price to buy the Daily News. Moreover, Singleton and Times Mirror forged a plan to sell preprint advertising together.

“I don’t think Dean has competitors,” says David Cole, of NewsInc. “Dean has business partners he hasn’t done business with yet.”

All this was too much for the Justice Department, which, in 1998, launched a yearlong investigation. In the end, Justice gave its approval to the advertising deal, but pushed to end the possibility that the Daily News could fall into Times Mirror’s hands. But Singleton’s lawyers convinced the feds to grant the Tribune Company (which bought Times Mirror) a 12-year option to buy the Daily News, since it would require approval from Justice and probably won’t ever take place.

Still, all is not well in Singleton’s California empire. Many of his papers are plagued by high turnover, due to the low salaries paid to reporters and editors. Singleton offers a blunt defense of his wage scale.

“We pay the salaries that a newspaper that size pays around the country,” he declares. “That’s the economic model that works for that size newspaper.”

Staffers who disagree, he says, should follow another career path—that of the young Dean Singleton.

“I was at the same place they were,” he said. “I started on small papers and went up the ladder as I got experience.” He doesn’t mince words: “You gotta climb the ladder. That’s what the business has always been about. That’s what it’s always gonna be about. You gotta climb the ladder and pay your dues.”

Singleton’s ascent would’ve been considerably slower were it not for the success of the Denver Post, the second paper he bought from Times Mirror. This time the surgery worked, and his accomplishment is widely recognized as a competitive triumph. As was the case in Dallas, Times Mirror unloaded the ailing Denver Post on him at a very attractive price—$25 million in cash, plus $70 million in long-term notes. Times Mirror also gave Singleton 45 acres near downtown Denver.

“Denver was a nice acquisition,” Singleton says with a grin. During the last year of Times Mirror ownership, the Denver Post lost $15 million, but the paper had certain things going for it, mainly a young, educated readership and an expanding market.

Singleton found himself in the middle of the country’s last great newspaper war—a war in which the Denver Post had been battling the Rocky Mountain News for more than a century, and a war that had been injurious to both papers. On the business side, Singleton moved to strengthen newspaper delivery and billing, both of which had been faulty under Times Mirror ownership. Editorially, the Denver Post decreased its crime coverage and stepped up its life-style and cultural coverage.

“I am not dumbing down the paper,” Dennis Britton, the editor at the time, told the New York Times in 1996. “I’m crime-ing it down and Pollyanna-ing it up, because I’m looking for a positive spin on things.”

The Rocky continued to bleed money. In 1997 Scripps, which owned the Rocky, panicked and began to offer the paper for a penny a day, less than $4 for the year; that gave the Rocky a circulation lead but ultimately cost Scripps $25 million. The Rocky, in 2000, finally gave up and asked to enter into a joint operating agreement with the Post. As part of the deal, Scripps paid MediaNews $60 million.

“We outmaneuvered them on the business side,” says Singleton. “We kicked butt on advertising and circulation. We were much more efficient. They blew a lot of money. We didn’t blow any money. We spent every nickel where it needed to be spent.” In the decade leading up to the JOA, the Rocky Mountain News hemorrhaged $124 million, while the Post earned $200 million.

Why didn’t Singleton simply wait for the Rocky to die, and then dominate the whole market? To begin with, he says, he had heard that one of Colorado’s wealthiest citizens was interested in the paper, and he was afraid of a new infusion of cash and a much longer newspaper war.

“I have multiple sclerosis,” he says. “I’ve beat the system for 17 years, but I don’t know that I’ll always beat the system. I don’t know at what point in time it will finally launch that big attack and throw me in the wheelchair or kill me. And I didn’t want to fight the battle for five more years.” He also wanted to accomplish something journalistically.

“The Post was a pretty darn good newspaper before the JOA. But I wouldn’t call it one of the five best in the country,” he says. “I want to give this market a world-class newspaper, and I couldn’t afford to do it with the battle going on.”

The goal of pushing the Denver Post into the small circle of top American newspapers remains elusive. In 2002, Singleton hired Greg Moore, a well-regarded editor from the Boston Globe, and gave him the resources he needed to hire top talent from the Chicago Tribune, Newsday and the Dallas Morning News. But talk of opening up foreign bureaus in the Middle East and Latin America dissolved as advertising revenues slipped, and the Rocky began to do better in its editorial competition with the Post than it had done in the decisive financial conflict. In a telling juxtaposition of events, the Rocky won two Pulitzer Prizes in April, a day before the Post announced a buyout plan intended to shrink its newsroom staff by 25.

Even so, the JOA continues to work, in large part because both the Post and the News benefit from the arrangement. Profits are divided 50-50, even though the Post has the Sunday edition. The arrangement is not very Singletonian, but he endorses it anyway.

“Can you squeeze a few million a year out by doing it another way? Perhaps,” he concedes. But, he goes on, “I’m not really into squeezing a few more million out. I’m not a money guy.”

Some editors who work at Singleton’s smaller papers give him credit for improving their publications; they insist his reputation as an enemy of newspapers is largely mythological. Kevin Keane edits the Lowell Sun, purchased by MediaNews in 1997. Before that, he worked at another Singleton paper, the Lebanon Daily News, in Lebanon, Penn. Keane notes that Singleton bought the Lebanon paper from Thomson, which had neglected it.

“When it rained, the mainframe got wet and the system went down for a day or two,” he says. “The computer system itself hadn’t been updated for a decade. Thomson didn’t seem to care. Dean brought in a new publisher and let him hire new people to lead the departments. In the course of two years, he sank about $1 million into plant upgrades, including a new front-end system and roof. As a result, the paper turned itself around.”

Among the papers in Singleton’s empire is Massachusetts’ Berkshire Eagle, which has a reputation as one of the nation’s finest small dailies. When Singleton bought the paper in 1995, it was nearly bankrupt. After seven years of ownership, Eagle veterans give him a mixed report card. Grier Horner, who worked at the paper for 30 years, notes that Singleton broke the union, fired staff members, and reduced salaries by as much as 30 percent; his own salary was cut by $9,000 a year. All the same, “Singleton has been respectful of the paper,” says Horner. “He hasn’t meddled with the newsroom. He’s given the newsroom autonomy.” Horner concludes, “He wasn’t the worst thing that could’ve happened to the Berkshire Eagle.”

L to R: Gary D. Pavel, chief pilot for MediaNews Group, and Capt. Gary Horst get ready to board the Falcon 2000. A months-long analysis preceded CEO Dean Singleton’s decision to trade in MediaNews’ previous craft for the 2000.

L to R: Gary D. Pavel, chief pilot for MediaNews Group, and Capt. Gary Horst get ready to board the Falcon 2000. A months-long analysis preceded CEO Dean Singleton’s decision to trade in MediaNews’ previous craft for the 2000.

The Eagle is hardly the largest of Singleton’s newspapers, but it remains on his travel itinerary. He checks in on properties large or small at least once a year, which helps explain why the Falcon racks up between 400 and 500 hours of flying time per annum.

“If you tend not to visit the newspapers, a lot goes on that you don’t know about,” Singleton says, adding, “If we get too many newspapers to visit, then we have too many newspapers.”

This philosophy provides job security for Gary Horst, one of two fulltime pilots on the MediaNews payroll—and so does Singleton’s loyalty to people he trusts. Horst’s been transporting Singleton since 1987, and along with Gary Pavel, who joined up five years ago, they take him to state-of-the-art facilities and throwbacks to a previous era. The airport outside Graham, Texas, near where Singleton was raised, falls into the latter category; it has an exceedingly short runway that ends at a barbed-wire fence, and is only staffed during the day. Fortunately, the folks in Graham know how to make their native son feel at home whether or not there’s a welcoming committee. If they’re going to arrive after hours, Horst says, “we call ahead, and they’ll leave the key under the mat for us.”

Horst can trace Singleton’s upward projectory by the planes he’s flown for him. The first was a Rockwell Sabreliner 40 that he doesn’t miss one bit.

“I’d give up flying if I had to go back to that,” he jokes. That was followed by a Hawker Siddeley HS125, a Westwind I, a Westwind II and the Falcon, which was purchased a couple of years back. But no matter the craft, or the status of his career, Singleton keeps his eye fixed on the bottom line. He wants trips to be as inexpensive as possible—”He knows how much gas the planes burn,” Horst notes—and he prefers to reach his destination without delay, even if the forecast doesn’t cooperate.

Horst laughs as he recalls a long-ago flight to Hamilton, Ohio, where Singleton once owned a paper. On that flight, they encountered dangerous weather.

“I told him, ‘We’re not going to be able to go in there,'” Horst recalled. “He said, ‘I don’t give an eff where we go. Get this plane on the ground!'” Horst rerouted to Cincinnati, which wasn’t Hamilton, but was close enough under the circumstances.

L to R: Gary Pavel and Gary Horst prep the Dassault Falcon 2000 for a flight to Oakland.

L to R: Gary Pavel and Gary Horst prep the Dassault Falcon 2000 for a flight to Oakland.

Singleton doesn’t make compromises like this very often. When Knight Ridder was on the block, MediaNews was portrayed in the press as a suitor for the entire company—but in the end, Singleton found a way to purchase only the papers he really wanted, without being saddled with what he saw as losers. That’s the way he does business, whether he’s shopping for a newspaper or a jet.

“Before we bought the Falcon, we looked at every kind of plane there was,” Singleton says. “We looked at the Gulfstream, but the fuel costs were too high for us. We looked at Citations, but they didn’t have the range we wanted. We looked at Lears, but they’re uncomfortable. None of them had what we wanted.”

And Dean Singleton is a man accustomed to getting what he wants.

A portion of this article previously appeared in the Columbia Journalism Review.