A Hawai'i real estate developer mostly active in repositioning small to mid-size hotels has filed personal bankruptcy with $22 million in debts after several years of unsuccessful efforts to save the properties from foreclosure.

Simon Bebb, who acquired some of his property from distressed sellers in the early 1990s, filed for Chapter 7 on Tuesday.

Bebb listed $207,032 in assets and $22.4 million in debts.

Though Bebb, 61, had his share of success in business that for him also involved investing in small commercial and residential buildings going back 20-plus years, his bankruptcy follows the loss more than a year ago of his last project, Waiakea Villas, a Hilo hotel Bebb bought in 1993 and converted into a condominium complex.

"I finally just threw in the towel," Bebb said. "I kept getting deeper in the hole."

Bebb, who majored in real estate at the University of Hawai'i and once owned roughly 600 rooms among four hotels, may be the biggest Hawai'i developer to file bankruptcy in the present economic downturn.

Bebb joins a list of other Hawai'i developers who have succumbed to bankruptcy amid the rise and fall in the economy and real estate market. Others include Chris Hemmeter, Herbert Horita, Peter Savio, Sheldon Zane and Amfac Hawai'i.

Savio, who filed bankruptcy in early 2001 and has since rebuilt his company, which is largely involved in converting apartment buildings into fee-simple condos, said he believes Bebb will rebound.

"He's got a lot of bounce," Savio said. "He's young enough to bounce back."

Bebb said he'd like to develop slim multi-story townhomes on small lots if he can find suitable land around O'ahu and financing partners. "I'll just have to start over," he said.

Much of Bebb's past trouble dates back nearly a decade. One difficulty, Bebb said, stemmed from a preferred lender of his, GE Capital, refusing to renew loans after deciding to scale back lending in Hawai'i in 2001, which left Bebb unable to refinance property including the 167-room Kuhio Village Resort in Waikiki.

Another major problem was the Sept. 11, 2001, terrorist attacks, which Bebb said led Holiday Inn to pull out of a franchise deal for another asset, the Continental Surf Hotel.

Bebb bought the two Waikiki hotels with fellow local developer Tom Enomoto in 1993, and a year later also acquired the Diamond Head View Hotel. But he lost all three to lenders.

Waiakea Villas, Bebb's last development property, headed into foreclosure proceedings about two years ago and took more than a year to sell.

"He was left with nothing else to use to work it out with creditors, and he had a huge debt," said Jim Wagner, Bebb's bankruptcy attorney.

Bebb's largest personal asset, according to the bankruptcy filing, is his one-bedroom condo residence in Hilo valued at $120,000 with a $100,000 mortgage.

According to the filing, Bebb earned no income in the past three years. Wagner said Bebb lived off savings, including $70,000 worth of gold bars from a Swiss safe deposit box and bank accounts containing $76,000 — liquidated within the past year.

Bebb also reported giving roughly $25,000 in gifts to girlfriend Julie Arata in the past year.

Among Bebb's debts are $13.8 million in court judgments, largely linked to property foreclosure sales, a $3 million lender claim related to Waiakea Villas and $300,000 owed to Hawai'i County for real property taxes and other fees.

Bebb also has automobile lease claims totaling $121,000 from Land Rover, Jaguar and Mercedes-Benz, dating back to 1999.

Two creditors have a combined $1.4 million claim against Bebb related to RightStar Hawaii, a group of mortuary and funeral services firms seized by the state. Wagner said the claims are related to loans Bebb indirectly received from Rightstar.

State and federal tax authorities claim Bebb owes about $2.5 million in income taxes for the prior three years, but Wagner said that's because Bebb's properties sold for much more than he bought them for. Tax authorities seek taxes on the gain even though Bebb lost the properties in foreclosure and received no proceeds because mortgages exceeded the sale prices.