Today, the 46-year-old Mr. Singleton, as CEO of Denver-based MediaNews Group, stands atop a fast-growing empire of 51 daily and 119 non-daily newspapers.
If you count by circulation, the privately held MediaNews is the seventh-largest newspaper company in the U.S., and 1999 looks likely to be its first $1 billion year.
Now Mr. Singleton is crashing the nation's second-largest market.
CIRCLING LOS ANGELES
Around the edges of Los Angeles' sprawl, he's leveraging one of his managerial hallmarks -- creating financially strengthened clusters of newspapers and folding in papers owned by other chains -- to form the California Newspapers Partnership. The CNP is a new entity that could force regional behemoth Times Mirror Co.'s Los Angeles Times to face heightened competition for ad dollars.
All of which is an outcome not many in the newspaper industry could have foreseen last decade.
Operating on other peoples' money, Mr. Singleton specialized in scoring distressed papers on the cheap and steering them back to growth, in no small part due to his tight rein on costs.
Some of his high-profile buys ultimately were unsuccessful. While Mr. Singleton won kudos for nursing the Denver Post back to health in one of the nation's last bona fide newspaper wars, he couldn't turn around the Dallas Times-Herald or the Houston Post.
Still, no one dared doubt his financial acumen. He frequently was compared with two other highly leveraged players of the 1980s newspaper world -- Ralph Ingersoll and Robert Maxwell -- and not always flatteringly.
Mr. "Ingersoll had [junk-bond kingpin Michael] Milken's money at the time, and the feeling was Singleton was a house of cards," says Scott Schmidt, a former publisher of the Los Angeles Daily News when it was owned by Tribune Co. -- before Mr. Singleton bought it. "There's no doubt who won today . . . I have the greatest respect [for him]. He built a company from nothing."
The magazine articles that followed Mr. Singleton's first flurries of big deals invariably described him in two ways, "baby-faced" or "boyish" and "maverick." Mr. Singleton survived, and succeeded, where his presumed peers of the '80s didn't.
He's been on the board of Newspaper Association of America since '93 and will accept the post of treasurer later this month. Some see this as his first step toward assuming the role of NAA president in four years.
All the same, the perception of him as a maverick, one outside the fraternity of traditional newspaper owners, is not entirely behind him.
"I think Dean is a little bit of an outsider," says Nicholas Penniman, who recently retired from publishing the St. Louis Post-Dispatch. "He operates in a way that requires him to make very tough decisions in certain circumstances . . . Part of the culture, the folklore of our business, is no one wants to take a news department down by 20% to 30% overnight. He has done that in a couple of cases."
Mr. Singleton's response: "So?"
More seriously, he adds, "I think you're dealing with perceptions from years ago. I can't remember the last time we took newsroom staff down" since MediaNews purchased The Oakland (Calif.) Tribune in 1992.
"The way we've done that is to do solid research and understand what the reader in a local market wants to read," says Mr. Singleton who adds that promotions and marketing have been instrumental in boosting readership.
"Dean has suffered from a bad press," says CEO Richard Scudder, Mr. Singleton's longtime partner at MediaNews. "When you buy a failing newspaper you have to make changes. And newspapers are nothing but people -- people and paper -- and saving a newspaper sometimes means [bringing in able people to replace] people who are not able."
Mr. Singleton's strong medicine for failing papers, has nonetheless resulted in a number of new practices that have caught on.
One is clustering, in which small and midsized papers located nearby each other pool editorial and production resources to reduce costs and make an attractive group buy for advertisers. Though often associated with cost-cutting, MediaNews' clustered papers in Southern California opened a news bureau in the state capital and started up a travel section.
Another is saving on newsprint -- newspapers' second-largest outlays after labor -- by printing smaller broadsheet pages on presses with 50-inch web-widths instead of the usual 54-inch. The move, popular with readers who overwhelmingly find the smaller size easier to handle, has been adopted by the Washington Post and the Los Angeles Times among other dailies large and small, and is being mulled over by many more.
Most unusual, perhaps, are his most recent moves in Southern California. He's consolidated most of his papers there with a clutch of papers owned by Donrey Media Group and one, the San Bernadino Sun, owned by Gannett Co., into the CNP.
That group, with a total circulation of about 600,000, is managed by MediaNews, which owns 59% of it, while Donrey owns 28.5% of it and Gannett Co. owns 12.5%. MediaNews' Long Beach Press-Telegram and Los Angeles Daily News, its two largest dailies in that region with a combined circulation slightly exceeding 300,000, are not part of CNP.
CNP can offer advertisers daily newspaper play over a wide swatch of Southern California.
'TIMES' NOT WORRIED
If once disparate local dailies now pose a threat to the Times by claiming strength in numbers, Times representatives -- at work implementing their own localized strategies in order to achieve ambitious expansion goals -- claim not see it.
"As far as ad revenue and circulation, no, there haven't been any issues there that are of concern," says a Times spokesperson. "But this is just an extremely competitive newspaper and media market. We're looking at it like that, rather than on focusing on any one individual or any part of the region."
The spokesperson touts the Times new regionalized products -- including Our Times -- which are aimed at serving what he calls "a local-local" niche in the area where the CNP dailies operate.
Times ad revenues were up 4.5% in 1998, but those results include the added lineage of a newly acquired local classifieds product The Recycler. The paper did not break out ad results excluding The Recycler, but "we acknowledge it wasn't a great year in '98 for ad revenue," says the spokesperson.
The Times is budgeting for an estimated 7% ad revenue increase.
Times publisher and Times Mirror CEO Mark Willes has set a long-term circulation goal of 1.5 million; circulation is now just under 1.1 million.
But Mr. Singleton's not loath to cut deals with the Times either.
Last year he sold a piece of a MediaNews affiliate company, Garden State Newspapers, to Times Mirror. He also produced a plan where his papers and the Times cooperate in distributing preprints for advertisers in the general Los Angeles market.
The latter was a move so unheard of it drew the scrutiny of the Justice Department. Since then, MediaNews and Times Mirror jointly bought a pre-prints distributor in the Los Angeles market.
Mr. Singleton's fond of stating that the American newpaper industry will winnow down to a mere handful of corporate owners, of which MediaNews will be one. Back in the beginning, few may have believed him. But his boast's getting easier to