Avery’s job at the $350 million May and Stanley Smith Charitable Trust and $150 million May Smith Trust paid a handsome $600,000 a year. On top of that, he billed the San Francisco-based trusts for legal work by his law firm. In March 2016, an Anchorage jury convicted Avery of numerous counts of fraud and money laundering, and on Monday he was sentenced to 13 years in prison. His crime? Burning through $52 million of May Smith Trust money in six months, the biggest private fraud case in Alaskan history. The trust was intended to support an elderly widow and go to charity after she died. Avery’s blizzard of spending in 2005 included purchasing an air charter company (despite having no background in aviation), Gulfstream executive jets, World War II military aircraft, Czech fighter planes, helicopters, rocket launchers, a patrol boat, and a yacht. He also paid off more than $600,000 in personal debt and bought a $700,000 home. Avery claimed he was simply an ambitious entrepreneur bamboozled by an untrustworthy business partner. The aircraft, he said, were meant to be used for legitimate money-making ventures, including training the Philippine Air Force and conducting US security details in Africa. Avery, now 57, is headed to jail — back to jail, actually, because he served time after pleading guilty in 2007 to related charges, but his conviction was vacated when a US Supreme Court ruling changed the definition of a certain type of fraud, setting him free.