One of Hawaii’s oldest and largest mechanical engineering firms filed for bankruptcy Tuesday in a move that aims to keep the 66-year-old business alive but also may result in its Native Hawaiian owners yielding to an Alaska-based investor.

Heide & Cook Ltd., established in 1946 by two workers in the plumbing trade who helped build Tripler Army Medical Center, filed a Chapter 11 petition listing assets and debts each at about $10 million.

The Honolulu-based company took in $25 million in revenue in its last fiscal year ended June 30 but couldn’t satisfy delinquent debts to lenders, landlords and equipment lessors despite a restructuring effort announced in August.

Earle Matsuda, Heide & Cook’s co-owner, president and CEO, said in the filing that the company has more value if it can restructure debts and stay in business.

"The petition was filed to insure that the company would continue its operations without affecting its customers, and to protect the interest of the company’s creditors and employees," said a statement issued by local bankruptcy law firm Wagner Choi & Verbrugge.

Heide & Cook proposes that a subsidiary of Chugach Alaska Corp., a Native Alaskan-owned conglomerate, provide $500,000 to sustain Heide & Cook through bankruptcy reorganization.

The petition said Chugach is expected to assume ownership of Heide & Cook and retain the majority of its roughly 100 employees.

Details on restructuring debts have yet to be proposed and will be subject to U.S. Bankruptcy Court approval.

Heide & Cook’s 20 largest creditors with debts not secured by company assets are owed $4.3 million. The largest of those is a $1 million claim by Chugach. The next-largest claim is $488,956 in credit card debt owed to First Hawaiian Bank. Debts owed to 15 vendors and subcontractors range from about $70,000 to $300,000 each.

Financial trouble for Heide & Cook stemmed from expansion into new lines of business during a robust economy in 2005, according to the company’s filing.

The company helped finance its expansion using loans and credit. But as the economy retracted, Heide & Cook ran into trouble, suffering an operating loss in 2008 — its first annual loss in 15 years.

In August, Heide & Cook announced a restructuring plan to focus on core business that includes heating, ventilation, air conditioning services, plumbing services and a division called AirReps Hawaii that rents and sells equipment including water and air purification and chilling systems.

Air conditioning and sheet metal divisions were refocused to select market areas, and a division for plumbing and fire protection was eliminated.

Also in conjunction with the restructuring, co-owner and chief financial officer Dexter Kekua retired.

Leading the restructuring were Matsuda, operations director and former University of Hawaii administrator Sam Callejo, company comptroller Ann Takamori and vice president Ross Sasamura.

"Our plan is to concentrate our sales and marketing resources in areas of our business that have the greatest potential for growth," Matsuda said in the restructuring announcement last year. "Heide & Cook has been doing business in Hawaii for 65 years … its ability to adapt to the economic landscape and reinvent itself over the years has made it one of the most respected and trusted mechanical contractors in the state."

However, six weeks after the restructuring announcement, Bank of Hawaii filed a lawsuit to foreclose on substantially all of Heide & Cook’s assets secured by $4.6 million in loans and credit. Two months later, in November, American Express filed a lawsuit to collect a credit card balance over $300,000.

Matsuda said in the bankruptcy filing that Heide & Cook explored selling the company to Chugach in November and that Chugach instead arranged to pay the Bank of Hawaii $1.4 million to acquire the $4.6 million debt against the engineering firm. The debt purchase occurred Jan. 19, a day after Bank of Hawaii received court approval to foreclose.

As Heide & Cook’s largest creditor, Chugach intends to acquire the firm’s assets through bankruptcy.

Chugach is a conglomerate set up in 1972 as part of the Alaska Native Claims Settlement Act enacted by Congress a year earlier. Native Alaskans became shareholders in Chugach corporations organized to administer land and money they received under the act.

If Heide & Cook is sold in bankruptcy, its business and well-branded name will live on, but not its local or 100 percent Native Hawaiian ownership.

Heide & Cook was established by Harold J. Heide and Jarrad T. Cook. The two met while working for a contractor building Tripler in 1946 and started their own business, H&C Plumbers, that year, according to an account by the Hawaii chapter of the American Society of Heating Refrigeration and Air Conditioning Engineers Inc.

In 1950 the business incorporated as Heide & Cook, and its first project was installing plumbing for a new subdivision: Aina Haina, the account said.

Cook died in 1965. Heide died in 1988.

Matsuda, the firm’s chief estimator who joined the company in 1974 as a sheet metal trade apprentice, took over in 1991. Four years later he bought Heide & Cook with Kekua and a third partner who later exited, the trade publication said.