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Man sentenced to three years for defrauding elderly widow of nearly $1 million

A financial advisor from Fox Island was sentenced to three years in prison Tuesday for stealing over $920,000 in life savings and inheritance from an elderly widow, according to a U.S. Department of Justice news release.

John S. Winslow, 57, worked as a financial advisor for a national financial services firm, which is how he came into contact with the victim, the release said.

The victim, a 78-year-old widow from Silverdale, has no children or immediate family members and is reliant on care programs to take her grocery shopping, to doctor appointments and other errands, according to court documents.

Over a period of four years, Winslow ingratiated himself with the victim to earn her trust.

“He did things to make me believe that he was my friend. He would bring me flowers and chocolate sometimes,” the victim’s statement said.

The victim “completely trusted” Winslow, giving him a copy of her mailbox key and allowing him to go through personal financial files at her house, her statement said.

What she didn’t know was that Winslow moved nearly a million dollars of funds from her brokerage accounts with the financial firm into an outside bank account outside his work’s surveillance system, the release said. He then moved those funds into his personal bank account.

He also told the victim that if she transferred money to his personal account, he’d return her funds at a higher interest rate than her banks, the release said. While visiting her at her home, he told the victim to call her bank on speaker and tell them what he instructed her to say.

Winslow would funnel the funds through layers of transactions to hide his illegal activity, the release said. For example, he purchased gold coins with the victim’s money, sold the gold coins to two retailers then deposited the proceeds in his own account.

He also failed to report any of the stolen funds on his tax returns, causing a tax loss of about $254,000, the release said.

According to court documents, Winslow used the stolen money on a variety of expenses, including a $20,000 hot tub, a $1,400 diamond necklace, a $100,000 down payment for a Fox Island home, a $10,000 down payment on a car and more.

Authorities indicted Winslow last year on four counts of wire fraud, two counts of mail fraud, four counts of money laundering and four counts of filing a false tax return.

His defense asked for a 12-month and one day sentence followed by three years of supervised release, according to court documents.

“[Winslow] is ashamed and remorseful that he ever made the terrible decision to take money from [the victim] - a woman who was his client and friend,” his defense said in its sentencing memorandum. “As a result of his crime, Mr. Winslow has lost his career, irreparably damaged his reputation, and put himself in nearly insurmountable financial debt. Mr. Winslow takes responsibility for his poor choices and wants to make amends in any way he can.”

The prosecution argued that Winslow’s persistence and intentional fraud deserved a 70-month sentence.

“Before each of these transactions, Winslow had the chance to stop and to ponder what he was doing to his victim. But he did not stop,” prosecutors said. “He wanted the gravy train to keep on going. He kept at it even after his withdrawals from (the victim’s) accounts triggered an elderly fraud alert. And he meant to bleed (the victim) dry. The only thing that stopped him from taking more of (the victim’s) money was getting caught.”

U.S. District Judge Tiffany Cartwright sentenced Winslow to three years in prison Tuesday.

The judge also ordered him to pay $1,175,475 in restitution to represent the amount of money stolen from the victim and the amount of unpaid taxes.

The victim sued his financial services firm, and they settled for $920,483. That means Winslow owes that amount of restitution to the financial services firm. He agreed to forfeit his home in Fox Island as part of his restitution obligation, the release said.

To obtain the settlement, the victim paid nearly $321,000 in legal fees and suffered financial loss.

Bonny Matejowsky
The News Tribune
Bonny Matejowsky is a breaking news and general assignment reporter for The News Tribune. Born and raised in Orlando, she studied journalism at the University of Florida, where she wrote for the independent student paper, The Alligator, and WUFT News. After graduating in May 2025, she discovered her passion for reporting in the Evergreen State as an intern for The Spokesman-Review.
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