The city of Portland has filed suit against the Shilo Inn, alleging the company owes the city and Multnomah County more than $314,000 in unpaid taxes from business at its Portland Airport hotel.

The lawsuit, filed Feb. 28, is the latest in a string of financial and legal troubles for the hotel chain and its owner, Mark Hemstreet, ranging from small claims for allegedly stiffing a contractor to a multimillion-dollar judgment against the company.

Hemstreet didn’t return requests for comment. City Attorney Tracy Reeve referred questions to Deputy City Attorney Simon Whang, who declined to comment.

City attorneys regularly file suit against companies that don’t pay their local business taxes. But lawsuits alleging a failure to pay hotel taxes are unusual. The city’s suit against Shilo says the company didn’t pay its hotel tax bill for July to December, 2018, and owes $252,000 in taxes plus $61,000 in penalties and interest.

Shilo Inn, like all hotels in Portland and Multnomah County, collected a 17.5 percent tax on every patron’s hotel bill. It did not turn that money over to the city and county as required, the lawsuit says.

On a smaller scale, Shilo Inn was sued in January by a locksmith who says the hotel didn’t pay him $148 owed for work on a padlock and keys at the chain’s hotel in Newport.

“I called about a month ago to the office and faxed the invoice,” wrote Jesse Day in his Lincoln County small claims filing. “Was told it would be taken care of. Never was.”

The company faced a much bigger legal ordeal in 2016, when a California judge ruled the Shilo Inn defaulted on several bank loans. The penalty: $20 million.

City attorneys in Seaside also sued Shilo in 2016 for failing to pay $143,000 in hotel taxes owed to the city. The case was dismissed after the company paid its bill. The hotel had previously paid another $146,000 to Seaside after it brought two similar cases.

The company, founded in 1974, has struggled in the past two decades. Twenty-seven of its 46 hotels filed for bankruptcy protection in 2001. Today, the chain has 22 locations, according to its website.

-- Gordon R. Friedman

GFriedman@Oregonian.com