When one of his clients asked to withdraw $50,000 just before Christmas, financial advisor Clayton Winkler knew something was off about the request. What followed was a long, delicate series of conversations with his client that revealed how close she had come to losing much more to a romance scam — and how critical an advisor’s role can be in protecting clients from financial predators.
“I’ve been a financial advisor for 25 years, and I believe we have the greatest career in the world,” Winkler said during a panel discussion at Osaic's ConnectED 2025 conference. In a conversation with Osaic's chief legal officer Saumya Bhavsar, Winkler said, “but sometimes the most important thing we do isn’t about investments — it’s protecting clients from themselves and from predators.”
Winkler, who is based in Michigan and is a part of Cobblestone Financial Serices, first began to worry in late November 2023 when his client Beth emailed him about needing an immediate and unexpected withdrawal. “She asked if there was a way to get $21,000 out of her account by the end of the day. It was unusual, but she explained it as a loan for a friend. I didn’t press too hard at that point,” he recalled, but explained there was no way to send money so quickly.
Three weeks later, Beth reached out again, this time requesting $50,000 to $60,000. Winkler picked up the phone. “When I asked her how she was doing, she said, ‘This is going to sound weird.’ That was the first big red flag.”
Beth explained the money was for her fiancé, a man Winkler had never heard of in the years they had worked together. “I was shocked. If someone is newly engaged, that’s a major life event. The fact she hadn’t mentioned it — that didn’t feel right.” Red flag number two.
The story grew stranger: the fiancé was supposedly working in construction overseas in Qatar and needed money to unlock a Bank of England account, which held millions. “When she said he just needed $50,000 to access $10 million, that was the biggest red flag of all,” Winkler said.
As Beth spoke, Winkler quietly waved in his case managers to listen in. They suggested asking if she had sent money that she had asked Winkler about previously, and how she sent it. Her answer confirmed everything.
Beth eventually admitted she had already sent $21,000, much of it borrowed through a credit union loan. But “the moment she said ‘Bitcoin machine,’ I was at 100% certainty it was a scam,” Winkler said.
Still, he chose his words carefully. “I didn’t say, ‘Beth, you’re being duped.’ Instead I said, ‘What you’re describing sounds like the common profile of a romance scam.’ That way she didn’t feel attacked or judged — and she kept talking.”
Over the next 65 minutes, Winkler worked to help Beth see the truth. “I asked her, ‘On a scale of zero to 100, how convinced are you this is real?’ After an hour, she told me she was only at a 30,” he said.
He repeated the warning signs, shared examples of similar scams, and even sent her links to articles. He also suggested she test the scammer by asking him for money to cover supposed tax costs. When he refused, her doubts grew.
“It wasn’t easy,” Winkler said. “I ruined her Christmas in a way — telling her that the love she was excited about was a fantasy. But she later told me she was thankful I approached it without judgment. She said I was the first person she had told the full story to.”
The experience reshaped Winkler’s own practice. “The term ‘trusted contact’ got used more in the six months after this incident than in my prior 25 years as an advisor,” he said. His office now emphasizes documenting trusted contacts and carefully verifying all unusual withdrawal requests.
He also stressed the importance of tone. “If I had said, ‘Beth, you’re being scammed,’ she might have shut down. Instead, by asking her to tell me more and making sure she didn’t feel judged, she opened up. That made all the difference.”
Romance scams, Winkler said, are only getting more sophisticated. “These criminals aren’t stupid. They’re calculated, they use emotional manipulation, and they play the long game. They say all the right things at exactly the right time.”
Looking back, Winkler takes pride not just in protecting a client’s assets, but in protecting her dignity. “Clients don’t need negativity when they’ve been through something like this,” he said. “What they need is someone to listen, to ask the right questions, and to stand by them when they can’t see the danger themselves.”
New C-suite and specialist roles signal that firms are treating AI as core infrastructure.
RIA dealmaking holds its pace in mid-2026 as two firms announce moves targeting first responders and West Coast growth
For the first time in 50 years, issuers could end up reporting twice a year – here’s what the SEC will expect of advisors.
It is the latest in a series of stunning and multi-million dollar FINRA arbitration awards that Wall Street firms have lost in the past few years.
After reporting a 20% lift in private banking gross sales tied to AI tools, JPMorgan is preparing more autonomous AI agents that could significantly increase client coverage across wealth management.
As $84 trillion prepares to change hands, advisors who treat estate planning as peripheral are quietly building a sieve, not a book.
In volatile markets, the advisors who win aren't the ones with the best calls - they're the ones whose clients stay the course.
