A former Citibank wealth advisor who swindled nearly $1.5 million from elderly clients was sentenced to serve 2 ½ years in prison Wednesday after telling a federal judge she “fell short” in her duty to protect her clients.

Helen Grace Caldwell, 59, who until 2021 was a vice president in the Michigan Avenue offices of Citibank, walked out of the federal courthouse following her sentencing hearing with orders to report on June 20 to begin her prison term.

“The only difference between Ms. Caldwell and a bank robber is that she didn’t have a mask and a gun,” said the U.S. District Judge Matthew F. Kennelly before issuing her sentence on one count of wire fraud.  “And actually in some ways it was worse because they trusted her, and she knew they trusted her.” 

Caldwell was also ordered to pay full restitution to her three victims, and to serve three-years of supervision after she is released from prison.

With a shaky voice and teary eyes, the once powerful banking executive and jet-setting film producer spoke briefly before she was sentenced, telling Kennelly she was deeply remorseful for the pain she caused and asked for the opportunity to prove she was capable of redemption. 

“I allowed myself to become overwhelmed and careless and I am so very sorry,” said Caldwell, who appeared in court with her attorney, Steven J. Rosenberg. “I had a duty to protect my clients to the best of my ability and I fell short.”

Caldwell’s case was investigated last year in an Injustice Watch series, Exploited Elders, which detailed massive failures within Illinois’ fraud protection systems designed to safeguard a skyrocketing number of old and vulnerable targets.

During her time at Citi, according to a plea signed by acting U.S. Attorney Morris Pasqual, Caldwell defrauded three elderly clients by convincing them to funnel their savings into her film production venture, Canal Productions.

Caldwell claimed the investments were going towards movies being produced and promoted by Canal, and she would share the profits with her client investors. Caldwell “knew that those representations were false,” she said in her plea.

Caldwell transferred hundreds of thousands of dollars of her victims’ film investments from the Canal bank accounts into her personal bank accounts, records show. She eventually used the money to refurbish a classic car, pay off parking tickets, repaint her home, book Airbnbs, and purchase home goods, clothing, and décor. Caldwell’s scheme seriously depleted her elderly clients’ life savings. 

“This wasn’t a mistake. It wasn’t poor judgment. It wasn’t an anomaly,” Assistant U.S. Attorney Corey Rubenstein said. “The level of deceit here was pretty high.”

In early January, Caldwell pleaded guilty to one count of wire fraud, a crime carrying a maximum sentence of up to 20 years. Rosenberg, Caldwell’s attorney, proposed a sentence of probation, according to a sentencing memorandum in early April, while Rubenstein suggested substantial incarceration and a three-year term of supervised release.

At the hearing, Judge Kennelly said probation would be “completely inadequate” for such a “reprehensible” crime. The typical sentence for this crime is at least 41 months, but he reduced it to 30 months because Caldwell has no previous criminal history.

One of Caldwell’s victims — identified only as Victim B — spoke during the hearing about how she considered the wealth advisor a close friend prior to discovering Caldwell was stealing from her.

“I feel as if the world around me has crumbled,” the woman told Kennelly.

Court records show the woman gave Caldwell $355,000 under the belief the money would be used to invest in a film production. According to the sentencing memorandum, Caldwell diverted much of the money to herself and lied to her victim about the status of the funds. 

The woman told the judge she asked Caldwell for her money back, and Caldwell simply told her “there was none.” The victim added the situation has caused her so much mental distress it has prevented her from performing daily tasks and has left her “imprisoned in my thoughts.”

Several in the courtroom, including Judge Kennelly, expressed skepticism at Caldwell’s expressions of remorse.

A screenshot from Helen Grace Caldwell’s personal website, which describes her as a financial services professional, award-winning filmmaker, and philanthropist.

Kennelly referred to letters of support from friends of Caldwell describing her as “falsely accused” and “innocent” and claiming she is being punished “for not being able to predict the future.”

Kennelly suggested the letters of support indicate Caldwell told the authors she did not commit these crimes. He said the statements “leap off the page, grab you by the throat and throttle you.”

Rosenberg said Caldwell had no contact with these individuals regarding the letters and they wrote those comments of their own volition. 

Kennelly also pointed to Caldwell’s statements from the hearing saying her actions were not intentional and stating she was not transparent with how the funds were spent.

“You can’t weasel your way out of it by saying you were careless and not transparent,” said Kennelly. 

Some involved in the case thought Kennelly was too lenient with Caldwell.

“I understand and respect the judge’s decision, but I would have preferred to see a longer sentence for someone who would use the prestige of her position as a Citigroup financial advisor to plunder the savings of seniors with dementia,” said Cook County Public Guardian Charles Golbert.

Golbert is suing Caldwell and Citi to repay the savings lost by Priscilla Eddings, one of Caldwell’s older clients who is now living in a nursing home with dementia. Golbert alleges the banking giant failed to adequately monitor Caldwell’s conflicts of interest.

“Now it’s time for Citigroup to finally make its customers whole and repay them the money that its employee defrauded from their Citi accounts,” Golbert said in an emailed statement to Injustice Watch.

Peter Duenas-Brckovich, the son of an alleged Caldwell victim who was not included in the government’s case, was also hoping for a longer sentence. “She’s a predator. She was preying on the weak,” he said.

Despite Caldwell’s scheme operating from within the walls of Citi’s Michigan Ave location, neither Judge Kennelly nor the attorneys mentioned the banking giant in their remarks. Rubenstein argued in court documents Caldwell effectively concealed her illegal dealings from Citi.

However, Duenas-Brckovich said “the biggest culprit is Citi,” as they provided Caldwell with an environment that enabled these crimes.

In court filings, Citi lawyers have argued the bank is not financially liable for Caldwell’s actions.

According to internal government documents, Citi first reported Caldwell to the Adult Protective Services division of the Illinois Department on Aging in March 2022 – four months after Caldwell left her job there.

Illinois officials did not take action because the client “was not being exploited by a family member, roommate, or caregiver,” Citi wrote in Cook County probate court documents.

Citi declined to comment on Caldwell’s sentencing.

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Eva Putnam is a spring 2024 reporting resident at Injustice Watch, through Northwestern University's journalism residency program. Eva's interests include youths, prisons, and the legal system, with a focus on investigative and narrative journalism. Originally from southern Wisconsin, she currently lives in Evanston to pursue her degree.