Williams tried a second time to get his money back. He called and wrote National Western, complaining about Pantaleoni. But instead of investigating, National Western slapped Williams with a surrender penalty of almost $15,000 and allowed Pantaleoni to hold onto his original commission, keeping him as an agent, according to the lawsuit. Though the insurer refunded the rest of his money, Williams had spent thousands of dollars on legal fees and other expenses related to his dealings with Pantaleoni. He sued both Pantaleoni and National Western in late 2017 for elder financial abuse, negligence and breach of fiduciary duty.

In April, a jury found National Western and Pantaleoni liable of elder financial abuse and negligence, and found Pantaleoni liable for fraud. It awarded Williams $3.1 million, declaring the insurer primarily responsible. The company appealed in September. Pantaleoni did not.

“Pantaleoni couldn’t have done what he did without the complicity of a company willing to turn a blind eye,” said Frank Fox, the attorney representing Williams.

This wasn’t the first time Pantaleoni was accused of improper behavior when working with seniors. In 2015, the California Department of Insurance filed a formal accusation against him, detailing his violation of insurance statutes in his dealings with a 74-year-old widow. The agency fined Pantaleoni and restricted his insurance license.

“I never did elder financial abuse and I never would,” said Pantaleoni, 62. However, in the case of Williams, he admitted he was negligent, in part because he didn’t have errors and omissions insurance, a type of liability policy, at the time. But he nevertheless disputed most of the other allegations in the lawsuit. “I did what the client wanted,” he said.

As for National Western, in 2010 the insurer settled a class action claiming it had misled seniors about penalties for withdrawing money from their annuities. National Western’s settlement included an accord with the California insurance commissioner requiring the company to make reforms in its sales, marketing and complaint procedures. The insurer denied any wrongdoing.

National Western, which uses thousands of independent agents to sell its insurance, had just two employees in its compliance department responsible for handling complaints at the time Williams tried to return the annuity, according to court documents. “Our independent agents are careful to ensure policyholders thoroughly understand the agreements they enter into when they purchase our annuity or life insurance products,” National Western’s chief legal officer, Rey Perez, said in an emailed statement.

When it comes to luring the elderly into a trap, some strategies are more aggressive than others. Earlier this year, a federal law enforcement officer outside Washington started to get glossy flyers at his home, inviting him to a free meal and a “retirement strategies workshop” at a local restaurant. “Expect to have a little fun and obtain some meaningful information with none of the usual financial double-talk,” one read.

By chance, the officer, who requested anonymity because he isn’t authorized to speak publicly, noticed that the retirement planner’s address matched that of an attorney he suspected was targeting the elderly. So on a sticky night in July, he dropped by the dinner, also hoping it might yield clues in a case of suspected elder fraud involving his now-deceased father. The dinner didn’t result in a breakthrough, but it did reveal how a business tries to persuade the elderly to invest in financial products they don’t need.

At an Italian restaurant in Virginia, more than a dozen elderly couples picked at their salads as the presenter asked them to fill out forms describing their assets and then complete worksheets while he extolled the virtues of annuities. “We can get you two to three times as much as a bank and keep you just as safe,” he said.