For the past three years, Portland's Tyee Films and Gary Adams Productions have been making a film for Robert Boisseau Pamplin Jr. This is no home movie. Shot in Georgia, Virginia and Oregon, A Place Apart tells the story of Pamplin and his father, complete with flashbacks to the Civil War and the Spanish Armada. It's apparently an epic tale, the center of which is the creation of the Pamplin fortune.

To narrate A Place Apart, Pamplin hired the actor Hal Holbrook. He selected Corbin Bernsen, who played Arnie Becker in the series L.A. Law, to portray his father. To play himself, Pamplin chose a little-known actor named Chad Bartulis.

A person familiar with the production says the movie is not yet complete. That's just as well, because the story may require a new ending--and not necessarily a happy one.

Although Forbes magazine listed Pamplin as Oregon's third-wealthiest man last year, with an estimated fortune of $575 million, WW has learned that, due to the meltdown of the industry in which his wealth rests, Pamplin may in fact may be worth only half that amount--or less.

It may be hard to feel sympathy for a man who owns a 60,000-acre cattle ranch, recently spent $25 million on a Civil War theme park and has a personal collection of Chinese art that has been appraised at $22 million. But conversations with textile executives, Pamplin employees and competitors make it clear that the quirky tycoon is staring down the barrel of a loaded gun.

Pamplin's most visible asset, The Portland Tribune, is losing money far faster than projected. His other media properties aren't much healthier. Another of his Portland-area operations, Ross Island Sand and Gravel, remains a solid business, but environmental liabilities threaten to swallow the company.

Pamplin's biggest challenge, however, is Mount Vernon Mills, the textile operation that makes up about 90 percent of R.B. Pamplin Corp, the family holding company. "I can't see that [Pamplin's textile business] could be worth anywhere near what it used to be worth," says Gary Smith, chief financial officer of Greensboro, N.C.­based Cone Mills, which, like Mount Vernon, is one of the country's largest denim manufacturers.

Having spent most of his adult life in the shadow of his father, the man who built the family fortune, Pamplin finds himself at age 60 in the uncomfortable position of having to fight to save his legacy.

Bob Pamplin Jr. declined to talk to WW for this story. Wendy Lane, who heads one of the three Portland public-relations firms that represent Pamplin, issued the following statement: "R.B. Pamplin has companies that are profitable, and Mount Vernon Mills is one of them. During tough economic times companies need to be conservative, and Bob has been conservative in dealing with his companies. Therefore, adjustments are made to companies, which might provide an incorrect impression."

Roger Chastain, Mount Vernon's CEO, did not respond to WW's interview request. Kevin Young, general manager of Pamplin's KPAM radio station (860 AM), declined to be interviewed; so did Steve Clark, publisher of Pamplin's Community Newspapers. Dwight Jaynes, sports columnist and president of the Portland Tribune, also declined repeated interview requests and forbade Tribune staffers and freelancers to talk to WW. "You guys clearly have an ax to grind," Jaynes says.

Despite that attempted blackout, background conversations with several Pamplin employees make it clear that his media ventures, particularly the high-profile Portland Tribune, are in jeopardy.

It's been a short honeymoon for the paper, which will celebrate its first anniversary in less than two weeks. When Pamplin launched the Trib a year ago, he attracted national attention for his bold challenge to The Oregonian. "Pamplin...has fired an effective first shot across the bow in what sounds and feels like a newspaper war," wrote Editor and Publisher magazine last March.

Nobody expected the startup paper, which is published on Tuesdays and Fridays, to be profitable immediately, but Tribune insiders say that the paper is losing money at an annual rate of between $8 and $10 million, three times the original projections.

The first sign of distress came as early as August, when the Trib's editorial and advertising staff gathered in the 75-seat theater underneath Pioneer Courthouse Square. The mood was seemingly upbeat as Publisher Don Olson and other top managers rallied the troops with glowing pep talks.

Then, according to people who were present, Pamplin strode to the front of the room. Jaw clenched, he noted that losses were already three times over budget. When--exactly when, he asked--was the free newspaper going to start generating some ad revenue? "That was the turning point," recalls one Trib writer. "He really threw cold water on the room."

In December, in another sign of the paper's declining fortunes, Pamplin fired Olson, the one person at the paper who had a successful track record of competing against The Oregonian. In the early '90s, Olson had run This Week, a free paper with a circulation of nearly 500,000, which snagged enough grocery advertising from The Oregonian to compel the Northwest's largest daily to buy it. (Olson also declined comment for this article.)

Then, in early January, Tribune president Jaynes wrote a column announcing that the paper was discontinuing home delivery on Tuesdays. Previously, the paper had been delivered free of charge to about 117,000 carefully targeted Portland households, with another 40,000 distributed through racks.

What Jaynes didn't tell readers was that the end to home delivery on Tuesday meant the Tribune's press run was being slashed from 157,000 to 40,000, a drastic step that saved printing and delivery costs but signaled a profound retrenchment. "If their strategy was to take on The Oregonian," says Business Journal Editor Dan Cook, "it clearly hasn't worked."

There are a number of possible explanations for why The Tribune has underperformed expectations.

Without question, the biggest factor is the dismal economy. Media companies have seen their revenues plunge. For instance, Dow Jones, the parent company of The Wall Street Journal, reported that advertising linage at the Journal was down 38 percent last year. "Clearly, Pamplin launched this thing [the Tribune] in the face of a recession," says newspaper-industry analyst John Morton of Morton Research in Silver Spring, Md.

Some observers say the paper's problem is its content, although the Tribune has won some fans. Several people interviewed for this article praised the paper's design, its sports and business coverage, and its reporting on stories such as the killing of Jose Mejia Poot. "I've liked it, particularly the focus on the schools and city government," says Judson Randall, formerly a senior editor at The Oregonian and now an advisor to student publications at Portland State University. (Oregonian executive editor Peter Bhatia did not respond to WW's interview request.)

But critics say that the Tribune has failed to carve out an identity and too often reads like Oregonian Lite. That's not surprising, because the paper employs at least a dozen former Oregonian staffers, led by Jaynes, who was a sportswriter and columnist at the Oregon Journal and Oregonian for more than 25 years. (The staff also includes three former WW writers.) "I don't think that the Trib has lived up to its potential," says Mick Mulcrone, a journalism professor at the University of Portland. "It's a welcome addition because it's another voice, but the paper is a lot stronger graphically than journalistically."

The Tribune may also suffer from what initially appeared to be a strength--an exclusively local focus. Since Sept. 11, Portlanders' appetite for international news has been stronger than ever.

Whatever view of the paper one takes, the undeniable fact is that the Tribune has failed to attract advertisers. Ed Tonkin, who runs Portland's second-largest auto dealership, was initially excited about having a mass-market alternative to The Oregonian but quickly lost his enthusiasm. "The Tribune is a high-quality publication, and we were one of their biggest advertisers early on," Tonkin recalls. "But our research showed that the ads just didn't bring in business."

The Tribune may be Pamplin's most visible media property, but it represents only a part of his communications holdings. He also owns Christian retailing, publishing and music businesses, some of which are also facing hard times.

Last November, Nashville-based Pamplin Music, which produced and distributed contemporary Christian albums, closed abruptly, resulting in 50 layoffs. "We spent six years trying to make this a profitable venture," Pamplin explained to CCM Update, a Christian-music trade publication. "We finally felt the need to close the divisions because of a lack of profitability."

(Pamplin's 18-store retail chain, Christian Supply, and his Pamplin Entertainment, best known for its Bible Man videos and traveling show starring former Eight is Enough and Charles in Charge star Willie Aames, remain in operation.)

It is too early to say how Pamplin is doing with his other newspaper operation, Tigard-based Community Newspapers Inc., which he acquired in the fall of 2000. In all, there are now 19 papers with a total circulation of 255,000 under the Community Newspapers umbrella. Unlike the Tribune, those papers were going concerns with established readership and revenue bases when Pamplin bought them.

It is clear, however, that plans to combine the suburban chain with the Trib to compete with The Oregonian have not been executed. Although the Trib and suburban papers share common classifieds, combined display advertising sales have been nonexistent. And although Jaynes and Pete Schulberg appear both on Pamplin's KPAM and in the Trib, neither their columns nor any of the Trib's other journalism makes it into the suburban papers.

The lack of synergy puzzles observers. "In other cities, the key to survival of second dailies is cross-selling with suburban papers," explains Morton, the media analyst.

"Shared resources would seem to be a no-brainer, but they haven't done it," adds UP's Mulcrone.

In addition to his newspapers, Pamplin also owns six radio stations in locations ranging from San Luis Obispo, Calif., to Spokane, Wash. His highest profile station, KPAM, purchased in 1997, is located in Portland. Although it is unclear how Pamplin stations in other markets are faring, his local properties, KPAM and KVAN in Vancouver, Wash., are floundering.

For the first couple of years that Pamplin owned KPAM, the station poked along as a Christian music station. But in 2000, at the same time he was moving into print journalism, Pamplin switched KPAM to news-talk. He hired longtime local talk-show host Bill Gallagher, poached Jaynes and Schulberg from The Oregonian and reportedly spent $1 million on billboards, and bus and newspaper ads heralding "Radio Free Oregon."

KPAM's debut was the most-talked about event in Portland radio's recent history, but the station has been a disappointment. In Arbitron ratings released last week, KPAM ranked 23rd out of 28 stations in Portland. In the key 25-to-54-year-old demographic, KPAM ranked 24th, five spots lower than in when it debuted. "They're not on the radar screen," says Tim McNamara, station manager of rival station KXL (750 AM). Industry insiders estimate KPAM is losing $5 million to $6 million annually.

If Pamplin's other businesses were trouble-free, his media flops might be easier to bear.

But Pamplin's Ross Island Sand and Gravel, located just south of downtown, also faces major challenges.

While the company, which employs 650 people, reportedly remains profitable, it now faces a potentially crippling liability: the cost of reclaiming Ross Island.

After more than 75 years, mining has ceased at the site that gives Ross Island its name. Although the company will continue to crush aggregate that it mines elsewhere, it is now required by the Division of State Lands to return the 300-acre site to as close to its natural condition as possible.

Under the terms of Ross Island's 1979 permit with DSL, reclamation would involve Ross Island obtaining 20 million to 35 million cubic yards of sand--the equivalent of more than 50 US Bank towers full of material--and filling Ross Island's lagoon, which was mined to a depth of 130 feet.

Ross Island officials argue, however, that the 1979 plan represents outdated science. To come up with an alternative, company officials have taken a highly unusual step, convening an "advisory panel" that includes city Commissioner Erik Sten and Metro Commissioner David Bragdon, both of whom have received campaign contributions from Pamplin. Also on the panel are the Audubon Society's Mike Houck and Ann Hanus, director of the Division of State Lands.

In July, that group is likely to recommend a different--and, Houck says, almost certainly less expensive--reclamation process to DSL. That's because the tentative proposal calls for only acquiring three to five million cubic yards of sand.

Nobody at Ross Island, the "advisory panel" or DSL will put a number on the potential savings.

Ross Island environmental manager Jim Rue argues that there might not be a savings, even though the company would have to buy 20 million fewer cubic yards of clean sand, because the company typically gets paid for disposing of fill.

But based on a recent series of transactions in which the Port of Vancouver, Wash., paid $2 per cubic yard for 400,000 cubic yards of clean sand, the revised plan could mean a savings for Ross Island of $40 million.

Ross Island is a major issue for Pamplin, but it too represents only a small part of his empire. About 90 percent of the annual revenues of the RB Pamplin Corp.--estimated by Forbes Magazine to be $895 million--come from the textile business.

Pamplin's textile company, Mount Vernon Mills, which is headquartered in Greenville, S.C., operates 17 plants in Alabama, Georgia, South Carolina, Texas, Mississippi and California, manufacturing denim, infant bedding and other textiles.

Due largely to low-cost foreign competition, however, the American textile industry is disappearing rapidly. In 2000, the industry lost money for the first time in its history. In the past year, according to the American Textile Manufacturers Institute, 103 mills closed; since Sept. 11 alone, three of the industry's largest manufacturers have declared bankruptcy. And a reduction in the tariffs on textile imports from China is looming. "There really hasn't been a period in the industry's history that has been this bad," says David Link, an economist for the ATMI in Washington, D.C.

Link and other industry sources say that Mount Vernon is healthier than most of its competitors, but it is not immune to the industry's ills. On June 21, 2001, for instance, publicly traded Thomaston Mills, a company in which Mount Vernon was the largest shareholder, declared bankruptcy. Then in November, the VF Corp., which makes Lee and Wrangler jeans and is a leading Mount Vernon customer, announced it was laying off 13,000 workers and moving aggressively to buy from foreign producers.

All these factors, say industry experts, have significantly eroded Mount Vernon's value. John Boland, a former textile-industry CEO who is now executive in residence at the Georgia Institute of Technology, says that even healthy textile companies are now worth half or less of their value in the late '90s. Put simply, that means if Mount Vernon was worth $500 million in 1998, it might only be worth $250 million today. "There's just no interest in textile securities in the investment community," Boland says. "None."

The upheaval roiling Pamplin's empire cannot be pleasant for a man who has spent much of his adult life attempting to measure up to his father, Robert Pamplin Sr.

It was the elder Pamplin who amassed a fortune during a 42-year career at Georgia Pacific. It was the elder Pamplin who, upon retirement as GP's CEO in 1976, bought Ross Island Sand and Gravel. It was the elder Pamplin who plunged in the textile business in 1982 with the purchase of Mount Vernon Mills.

In his book Heritage, Pamplin Jr., an only child, muses at length about the challenge he faced. "Like any son faced with an extraordinary father," he writes, "I understood there could be only one way [to succeed], namely, finding something new."

In his quest, Pamplin has racked up eight college degrees, including two Ph.Ds--one from Portland's Western Seminary and another from California Coast University (an unaccredited institution that has no campus)--and 10 honorary degrees.

Pamplin has co-authored 13 books and been named Portland's First Citizen, Oregon's Entrepreneur of the Year, and the Outstanding Philanthropist of 2000 by the National Society of Fund Raising Executives. His nine-page résumé--which until recently could be found online--testifies to his generosity. Pamplin Sports Center at Lewis & Clark College; Pamplin School of Business at the University of Portland; Pamplin School of Business at Virginia Tech (his father's alma mater); and Pamplin Park, a $25 million Civil War theme park in Petersburg, Va., are but a few of the gifts that bear the Pamplin name.

The launch of KPAM and the Tribune marked a departure for a man whose reputation had been based more on his enthusiasm for giving away money than his ability to make it.

Yet in the past year, with the erosion of the businesses his father built and the losses sustained by his own media ventures, the challenge for Bob Pamplin Jr. has grown.

Inevitably, he will be compared to his father, who, at age 90, still comes to work nearly every day, occupying an office adjacent to--and bigger than--his son's.

But will A Place Apart, the movie Pamplin commissioned, have a happy ending? That depends less on whether he can ever equal his father than on whether he can hang on to what the old man built--and salvage a media business that has so far brought more scrutiny than acclaim.

For more information about Bob Pamplin, see www.pamplin.org. For more about the meltdown of the textile industry, see www.atmi.org

You can find WW's September 2000 cover story on Pamplin, "Citizen Bob," at www.wweek.com/html/leada092700.html .

Nike founder Phil Knight remains Oregon's wealthiest citizen, with a fortune of $4.9 billion, according to Forbes. Klamath Falls window maker Dick Wendt leapt over Pamplin on Forbes' 2001 list, with a net worth estimated at $700 million.

While KPAM struggles to attract listeners, the Trib provides a direct KPAM competitor, KXL host Lars Larson, with free publicity in the form of a weekly op-ed column.

Pamplin announced plans to give Ross Island to the City of Portland last year. He is holding private meetings with Mayor Vera Katz to iron out the details. Records show that the two and their representatives have met five times in the past year to discuss the issue.

R.B. Pamplin Corp. ranked first among Oregon companies in soft-money contributions to the national Republican Party in 2001-2002, with donations of $150,000, according to the Center for Responsive Politics. In 1999-2000, the company ranked second, with contributions of $135,000.

At 1.1 million square feet, Mount Vernon Mills' Trion, Ga., denim plant is the largest such manufacturing facility in the country.