With friends like this...

For most of the past two decades, Bob Orians led a charmed life.

As a top Portland venture capitalist in the '80s, he scored big successes financing startup companies. As a real-estate developer in the '90s, he helped pioneer the renaissance of inner Northeast Portland, putting such landmarks as the soul-food mecca Doris' Cafe on the map.

Orians lived well, first on the waterfront in Lake Oswego, then in a series of elegant Irvington homes. He also had vacation homes in Palm Desert, Calif., and Vashon Island, Wash. Superbly fit, the 54-year-old longtime Multnomah Athletic Club member captained the club's tennis team to a city championship this year.

But in recent months, Orians' secret life has shattered the image of prosperous respectability he worked so long to build. Earlier this year, Multnomah County grand juries indicted Orians on separate charges of criminal theft and criminal securities fraud. He has resigned from MAC and lost the support of loyal friends. "I think he's a con artist," Rosie Dean, the owner of Doris' Cafe, now says.

News of Orians' descent into the criminal-justice system took former peers by surprise. "I'm shocked," says Chet Paulsen, the CEO of Portland's Paulsen Investment Company, who knew Orians in the '80s. "In every business dealing that I had with him, he was a stand-up guy."

Orians' luck hasn't completely evaporated. He sat in Multnomah County Court last week nervously chewing gum and scribbling notes to his attorney. But on Friday, the judge dismissed the fraud charges against him on a technicality, leaving Orians free. At the same time, his ability to stealthily approach investors will never be the same.

In an age when identity theft and other high-tech threats to financial security generate considerable anxiety, Orians' story proves that a silver tongue and a lot of brass remain effective tools for separating investors from their money. "The assumption is that [Orians] has got to be legit because he's so visible," says Dr. Ken Scissors, a former tennis partner and investor of Orians'. "He uses the fact that [Portland] is a small community to his advantage. Nobody sane would imagine getting swindled by someone who has no place to hide."

Like F. Scott Fitzgerald's Jay Gatsby, Bob Orians is a mysterious figure who propelled himself from modest beginnings to lofty heights. "Bob grew up very poor," says his ex-wife, Pamela Massey, who married Orians in 1979. Orians' father, according to Massey, died alone in a mobile home in Walla Walla, Wash.

Also like Gatsby, Orians has been less than honest about his history. Although he reportedly told Massey and others that he had an economics degree from the University of Oregon, records show that he attended St. Martin's College in Lacey, Wash., from 1966 to 1967 and transferred to the University of Oregon in September 1967, graduating from neither.

In the '70s, Orians worked for six Portland stock brokerages in seven years. But he settled down in 1979, establishing Orians Investments, a firm that combined venture capital and investment banking.

Portland's economy was then mired in a recession, and even blue-chip companies struggled to obtain financing. Local entrepreneurs who couldn't find money elsewhere came to Orians. "Bob was a guy who raised a lot of capital for a lot of people," says Steve Wynne, a lawyer who advised startups and later co-founded the law firm Ater Wynne.

With his charm and unshakable confidence, Orians easily found wealthy investors willing to take a flyer on unproven companies. "He came across as a winner," says one former client. "He was like the son you never had."

Orians consumed business magazines and books voraciously, Massey recalls, always searching for the next big thing. "He's a workaholic, as 'Type A' as they come," she says.

His talents were best illustrated in Swift Energy, his earliest and largest success. One day in 1979, despite operating nearly 3,000 miles from Wall Street and the oil patch, Orians, who then specialized in oil and gas limited partnerships, cold-called a Midwestern pipeline company executive named Earl Swift and convinced him start his own exploration company. "He [Orians] was very competitive and very focused," recalls Larry Black, founder of the Portland brokerage firm Black and Company.

In 1981, two years after Orians began financing Swift Energy, Orians Investments and Paulsen Investment Co. took the Houston-based company public. Earlier this year, Swift's stock was worth nearly $1 billion.

Orians' clients prospered in the early '80s with investments in such companies as Swift, Beaverton's Timberline Software, and Pensa, the company that became Avia Shoes. Timberline went public, and, after explosive growth, Avia was bought by Reebok.

Documents from Orians' 1984 divorce from Massey show that he owned shares or options in more than two dozen companies and limited partnerships. But Massey says that he frittered away his investments. "He never had the money to exercise the options because he was out spending it," she says.

In January 1987, in the midst of a soaring stock market, Orians Investments abruptly ceased operations. "The thing that's interesting is why did he disappear from the scene?" Wynne says today. "The startup, entrepreneurial thing was just getting started, and he was one of the few guys doing it."

Part of the answer to that question can be found in the National Association of Securities Dealers archives, which show that Orians ran afoul of regulators in 1987. David Tatman, director of enforcement for the Oregon Division of Finance and Corporate Securities, explains that Orians invested clients' money without their knowledge or permission. "That's a pretty fraudulent act," Tatman says.

In 1988, the NASD revoked Orians' license after he failed to pay a $2,500 fine. (His check bounced.) The revocation drew no press attention, and many of Orians' current friends didn't know that he was ever in the securities business, let alone bounced out of it.

Orians' failure to pay the modest fine is puzzling, but a review of court records suggests he may have faced more pressing problems. In the late '80s, documents show, a number of clients and business associates sued him for allegedly failing to repay loans or fulfill other financial obligations. Over the years, more than 20 such suits would be filed, several resulting in substantial settlements or judgments.

Although some former investors say Orians has pocketed millions from various schemes, the true extent of his efforts remains unclear.

In September 1987, for instance, Orians borrowed $100,000 from Rod Johnson, who had built KWJJ into Portland's most popular radio station before selling it for $2.5 million in 1973.

But when Johnson died in 1992, his widow discovered that nearly all of their money had vanished. "What was a very sizable estate was down to practically nothing," she says today.

In 1993, Betty Johnson sued Orians in Multnomah County Court, seeking return of the $100,000 plus interest. (Johnson doesn't know why her husband loaned the money to Orians or what Orians did with it).

"He's very charming and very nice," Johnson says of Orians. "But he's far more dangerous than a common criminal who comes at you with a gun or a knife." Johnson says that not only did Orians fail to repay her husband but that, in the first place, he had taken advantage of Rod Johnson's diminished mental state--her husband suffered from Alzheimer's disease, she says, which had grown progressively worse after 1982.

In a 1993 out-of court settlement, Orians agreed to repay Johnson, but he has failed to do so. Orians has claimed poverty, Johnson says, and employed such tactics as bringing his two hearing-impaired children to negotiating sessions. Now 77 and facing old age with a hefty mortgage, Johnson adds that Orians acted as if he rather than she were the victim. "He's sort of like a bewildered child," she says. "It's as if I'm causing trouble for him."

Unbowed by the NASD and the growing stack of lawsuits, Orians began the second chapter of his career. A local company that he'd financed, All American Frozen Yogurt, prospered through franchising; meanwhile, one of Orians' friends, the late Tiger Warren, was making a splash with healthy Mexican food chain Macheezmo Mouse.

Orians decided to follow suit. "He was convinced that low-fat fast foods were the future," Massey says. Orians concentrated on three food operations in which he held investments: a local restaurant chain called Trapani Pasta, All-American, and the Oregon and Washington franchises of Wally "Famous" Amos, who started the gourmet cookie trend in the late '70s.

Amos, now a Hawaii-based author of self-help books, doesn't recall how he met Orians but mentions him repeatedly in his autobiography. "Bob was a dynamic, smart businessman," Amos told WW. "He really supports the community and is a fine person. We're good friends still."

But the fledgling cookie empire crumbled. "We didn't have enough capital," Amos says. "We gave it our best effort, and it just didn't work out." The yogurt company also languished, and Trapani Pasta, despite high-traffic locations at the Sea-Tac airport and Pioneer Place, went bankrupt.

Orians never missed a beat, however. After a brief sojourn in Vancouver, Wash., from 1989 to 1991, he moved to Irvington and began the third chapter of his career. "Bob doesn't have multiple personalities," Massey says. "He has multiple lives."

In 1992, long before Nike opened its outlet on Northeast Martin Luther King Jr. Boulevard or the old Standard Dairy became Billy Reed's, Orians began acquiring properties in the MLK corridor, most notably a rundown brick industrial building at Northeast Russell Street. "All of a sudden this guy [Orians] showed up and was buying commercial properties and developing MLK," recalls Bill Leigh, a longtime Northeast real-estate broker.

Just as Orians raised his profile in the securities business with Swift Energy, he made a splash in Northeast by latching onto Doris' Cafe, then housed in its original location near Emanuel Hospital. Having heard about Doris' growing popularity, Orians made owner Rosie Dean an offer she couldn't refuse: to be his anchor tenant in the smartly refurbished 333 Russell building.

It would be hard to find an odder couple than Orians and Dean. A Republican and a health fanatic, Orians favored starched shirts, never had a hair out of place and dined frequently in Portland's top restaurants with his wife Siri, a ringer for Inside Edition host Deborah Norville who is 20 years his junior. Dean, in contrast, was a generously proportioned single mom who kept her financial records in a paper bag, staffed her restaurant with street kids, and raised three sons and funded her restaurant by working long shifts in a Nabisco cracker factory.

Yet the two hit it off--at least initially. "He was a smooth talker, and I had no reason to not to trust him," Dean recalls. "I take people at face value."

In 1993, The Oregonian published a one-and-a-half-page-long history of Doris' titled "The Rib Queen Meets the Money Men." The write-up became Orians' calling card. "After the Oregonian article, a lot of people wanted to meet him," says a former employee. Orians' refurbished properties attracted some of the city's leading nonprofits, including the Portland Public Schools Foundation, Saturday Academy and the Enterprise Foundation.

In 1996, The Oregonian's Margie Boulé penned a column extolling Orians' altruism. When a four-alarm fire broke out near a coffeehouse Orians co-owned, Boulé reported, he sped down to the shop and served free food and drinks to the firefighters. "Blessed are those who give without remembering and take without forgetting," Boulé wrote, quoting Princess Elizabeth Bibesco of Romania.

But even as Orians' reputation blossomed, court records show that he continued taking liberties with other people's money.

In March 1995, Orians admitted in Multnomah County Court that he had failed to repay a $184,000 loan from his former best friend, Portland psychiatrist Dr. Ward Smith. In June 1995, Orians also admitted that he had sold $145,000 worth of stock for Smith and kept the money.

Today, Smith, who with two partners sold 55 percent of a medical-research firm for $9 million in 1999, finds it difficult to talk about Orians. "This has caused me enough pain," he says. "Our kids grew up together and are friends still. There was more to this than just an investment."

Like Smith, Dr. Ken Scissors, an internist, and his wife, Colleen, a criminal-defense lawyer, trusted Orians without checking his background. "He often presents the deal as needing to be made right now or the window of opportunity will close," Ken Scissors explains. "He disses lawyers and contracts, and appeals to just dealing with trusted friends and neighbors on a handshake."

But soon after giving Orians money to invest in two buildings he claimed to own, the Scissorses say that they discovered Orians didn't own either of them. He had already surrendered title to one to satisfy a debt and had previously sold the other to another buyer. (That buyer was Ovid Uman, who established the critically acclaimed Tidbit Gallery in an Albina building that he leased and later bought--or so he thought--from Orians.)

Doctors and lawyers might not be the savviest real-estate investors, but Orians' longest-standing and reportedly largest backer, Edward B. Hart, had no such excuse. Hart, a 77-year-old Lake Oswego resident, is the former CEO of Payless Drugs, a company he built before the Portland-based chain was purchased by Green Equity Investors in 1994 for $1.2 billion.

Hart, who declined to be interviewed, reportedly made money in the '80s investing with Orians, and records show that he later bankrolled Orians' real-estate ventures. Late last year, however, their relationship foundered. In a lawsuit filed in Multnomah County Court, Hart accused Orians of stiffing him on a $10,025 debt and skimming $31,175 in rent from a building Orians managed for him.

Much of that rent came from Doris' Cafe. Initially, Dean says, she thought Orians owned the building her restaurant occupies. In recent years, however, Hart occasionally called her asking where her rent check was. But Dean says Orians told her not to worry. As it turned out, Orians was pocketing her rent, which Dean suspected but didn't want to believe. "A lot of people told me he beat them out of things, but he'd never done anything to me," she says today.

Dean is furious at her former friend. "I worked two jobs just to keep the place going," she says. "But if Mr. Hart ever came after what I owe him, I'd be gone."

Just as Jay Gatsby's unsavory history eventually overshadowed his carefully constructed image, Orians' shady dealings ultimately caught up with him. Ironically, after years of targeting wealthy investors, Orians was brought to prosecutors' attention by a man who had never previously made an investment of any kind.

Kirtley Wade Burggraf is a stick-thin piano tuner who augments his earnings by playing an alto sax in a jazz band. Burggraf, 51, never had a dime until his mother died in 1997--and soon after meeting Orians that same year, he says, the money was gone.

The two met at the Albina (then Steen's) Coffeehouse, then jointly owned by Orians and Portland jazz drummer Ron Steen. Orians made a strong impression. "He's very intelligent, he's charming, he has movie-star good looks and knows how to gain people's confidence," says Burggraf.

In early 1998, Orians asked the piano tuner if he wanted to buy Steen's share of the coffeehouse. "He told me I could double my money in a couple of years," recalls Burggraf.

The plan was that Burggraf would assume half ownership and manage the coffeeshop for $1,500-a-month salary and half the profits. But after the first month, Burggraf says, Orians paid him only $500--and the check bounced. Orians also informed Burggraf that there were no profits, only losses.

Burggraf's inheritance and subsequent costs--nearly $100,000 in all, he says--are gone. Although the coffee shop exists, Burggraf says that the company he bought into does not, nor is his name on the title of a North Portland house that he and Orians bought together.

Over the past three years, Burggraf doggedly researched Orians' past and nearly buried Karin Immergut, then the Deputy Multnomah County District Attorney in charge of white-collar crimes, underneath a mountain of information.

In April, Immergut convinced a Multnomah County grand jury to return five counts of criminal theft against Orians relating to his dealings with Hart, Dean and Uman. In August, she convinced another grand jury to return a criminal securities-fraud indictment for Orians' dealings with Burggraf. "Essentially, I think [Orians] engages in a Ponzi scheme," she explained to Judge Jean Kerr Maurer in a hearing on theft charges in mid-October. "Every time he finds somebody whom he can borrow new money from, he essentially pays off whoever's breathing down his neck the most."

Despite Immergut's objections, the theft charges against Orians resulted in civil settlements, first with Hart and later with Uman. The former gallery owner was not mollified by the result. Orians, he says, "is slime, slime, slime."

On Nov. 2, Multnomah County Judge Kimberly Frankel tossed out the criminal securities-fraud charge against Orians because the statute of limitations had expired. Frankel's ruling had nothing to do with the merits of the charges against Orians but rather hinged simply on whether the state had filed its case within the required three years from the date of the alleged crime. Once again, Orians got away clean.

Not everybody is convinced that Orians sets out to steal. "He's made people money in the past, but he got a little stuck, and when he failed, he couldn't accept it and just got in deeper," says Smith, his former best friend.

Massey takes a less charitable view, saying her former husband's problem is that he was in too much of a hurry to get rich. "He wanted to be what his clients were, but he didn't want to take the time to earn it," she says.

But Colleen Scissors, whose criminal-defense practice included representing a follower of the Bhagwan Shree Rajneesh accused of plotting to kill U.S. Attorney Charles Turner in 1995, says that Orians' actions cannot be explained by incompetence or greed. "He is a menace to society," she says.

After repeatedly denying interview requests, Orians briefly acknowledged last week that he had made mistakes and hoped to change. "I'm trying to be a better Bob," he told WW before hanging up.

For Burggraf, Frankel's ruling was a bitter blow. "I'll be surprised if there aren't more victims out there in the future," Burggraf says. "He's addicted to other people's money."

An earlier

story about Orians (see Rogue of the Week, Aug. 1, 2001) caught Orians' fellow tennis players at the Multnomah Athletic Club by surprise, says the haberdasher John Helmer Jr., who played on the tennis team Orians captained.

Orians previously won the Irvington Tennis Club singles title at the USTA's 5.0 level, which is the top level before the "open" designation. He currently plays at 4.5.

A 1995

article about the redevelopment of the Martin Luther King Jr. Boulevard corridor cited a number of institutions but only two individuals: Billy Reed and Bob Orians. "Orians was a pioneer in renovating the MLK corridor," says Mike Warwick, a former official of the Eliot Neighborhood Association.

Orians now runs Communication Enterprises of Oregon Inc., a North Portland cell-phone dealer.

David Tatman, director of enforcement for the state's Division of Finance and Corporate Securities, estimates that there are fewer than five criminal securities- fraud cases filed annually at the county level in Oregon.

Deputy Multnomah County District Attorney Karin Immergut assisted special prosecutor Kenneth Starr in his investigation of President Bill Clinton. Immergut left the county DA's office for the U.S. Attorney's Portland office at the beginning of November.

WWeek 2015