Emails show that former Oregon Gov. John Kitzhaber approved a state investment to help financially troubled Portland businessman Sho Dozono.

In April 2012, the state economic development agency Business Oregon recommended Kitzhaber use the governor's strategic reserve fund to aid Azumano Travel, which has held the state's exclusive travel contract since at least 2006.

The recommendation to Kitzhaber acknowledged Azumano had lost money the previous three years and paid employees an average of less than $40,000 annually. "This looks like a good investment to me," Kitzhaber wrote in an April 26, 2012, email to his business adviser, Scott Nelson.

The state gave Azumano $40,000 outright and loaned the company $260,000 at 2 percent interest. Azumano stopped repaying its loan in early 2014 and Dozono declared bankruptcy this year, owing $148,000 in debts to the state. The Kitzhaber emails were released last month in response to records requests. Kitzhaber and Dozono could not be reached for comment.