Case Study: Alyssa Milano Sues Business Manager $10 Million for Fraud

On the heels of Johnny Depp’s alleged frauds by both his business manager and lawyer, another famous entertainer has lost millions. Alyssa Milano and her husband (a talent agent at CAA) recently alleged her business manager, Hellie, Hoffer, and Company (“HHC”), committed fraud, theft, negligence, and breach of fiduciary duty, to the tune of $10 million in damages.

Enchanted by Finance

Milano’s allegations (per her complaint published in Hollywood Reporter) reveal a litany of red flags and sordid details, including plagiarized signatures, unauthorized withdrawals, unauthorized loans and investments, a mortgage default, insurance policy lapses, and unpaid income taxes. Milano’s entire financial world is now in complete disarray.


The lessons we can learn from entertainers like Depp and Milano are just as useful as those learned from fraud against sports stars like Tim Duncan and Clinton Portis. Many of these cases share one crucial element: an individual provides financial power to a trusted advisor with no checks and balances to ensure the individual is not being taken for a ride on the fraud rollercoaster.


It’s important to note that Milano’s charges against HHC detailed in this post are just allegations and yet to be proven in court. HHC also filed a counter-suit which cast blame on Milano’s husband and said their spending was out of control while Milano refused to acknowledge the problem. However, the suit did not appear to offer rebuttals to the allegations of forgery and fraud.

Role of HHC

HHC was Milano’s business manager entrusted “with the management and control of her finances, including collecting income and compensation on her behalf, maintaining and safeguarding her bank and investment accounts, paying her bills, overseeing her household and employees and generally managing her personal and business affairs. Defendants were also responsible for Milano’s tax matters.”


HHC had the keys to the castle.


The alleged charges include:

  • HHC made multiple loans with its clients’ money to shuffle funds between clients, including loans to and from Milano. “Plaintiffs are informed and believe, and based thereon allege, that these maneuvers were necessary to shore up the liquidity of HHC clients with cash flow problems created by the same mismanagement and lack of internal controls that afflicted the Plaintiffs.”
  • HHC invested at least $900,000 of Milano’s money into four companies that HHC had previously invested in. Further, HHC transferred funds without obtaining Milano’s signature; instead HHC scotch-taped a copy of Milano’s signature on a $150,000 wire transfer form.
  • HHC’s misconduct continued even after they were fired, forging Milano’s signature to deposit a $25,919 check into their account as well as paying $25,350 in “interest” payments to other HHC clients using forged signatures.
  • A home improvement project received citations from Ventura County, CA, “that would have been easily fixed with a day or two of work.” For five years, HHC did not correct the issue or notify Milano, and Milano received a County Lien on their residence and $376,950 in fines.
  • Milano received a Notice of Default on her mortgage because HHC had eight later mortgage payments over a 13 month period.
  • HHC did not pay Milano’s 2013 and 2014 federal income taxes. HHC told Milano – via text message – that they had negotiated a deal with the IRS that never happened.
  • Milano’s insurance policies all lapsed, and “HHC deliberately concealed its failure to pay the premiums, and the resulting lapse in coverage…HHC forged Plaintiffs signatures on documents necessary to reinstate the policies, in order to furthrer conceal the lapse in coverage.”

How could this all possibly happen?

Who's the Boss?

Milano granted HHC to be the Trustee on her two trust accounts. This gave HHC control of her money and the spending of her money from the trusts. This is similar to granting someone power of attorney on your accounts.


But here’s the kicker: In the decade that HHC worked for Milano, HHC did not provide Milano or her husband with a single financial statement! HHC assured Milano, “I can tell you without a doubt that your finances including investments are in good shape.” Despite these assurances, Milano should have periodically reviewed and verified that her finances were in order.


When Milano received a call from her bank that her mortgage was in default, she finally knew something was amiss. As her financial situation deteriorated, Milano found it difficult to obtain information from HHC. Milano brought in a new business manager who then began to unravel and uncover the financial mess. HHC was then fired.

Lessons Learned

If you have not independently reviewed your financial statements or activity in one year, let alone ten years, this is imperative for you to do. When you provide a business manager, financial advisor, money manager, etc., with control over your finances, you or an independent advocate like BrightLights has to maintain control and understand what is going on under the hood.


Some ways you can think about this:

  • Would you have noticed what Milano missed when her business manager took out $900,000 in her name? How would you have noticed this? Are you reviewing your inflows/outflows of money each month and to whom checks are being written?
  • Would you have ensured that your income taxes were paid? How so? Would you require confirmation documents from the IRS that your tax return was received and accepted? Would you look to see how much you paid in taxes to see if it roughly lined up with your earnings?
  • Would you have known if you mortgage was being paid? Are you monitoring your bank account to ensure mortgage payments have been on time and are not delinquent?
  • Would you know if your insurance policies were being paid? Are you monitoring your policies to ensure payments have been on time and are not delinquent?

 These suggested reviews would verify that your employees are doing their job and mitigate the risk of financial wrongdoing. Blindly trusting someone drastically increases the risk that fraud may occur. Their opportunity to commit fraud is now endless: they have control of your money, and they know you are not reviewing your finances.


Although the majority of people with this financial power do not abuse it, we don’t have a crystal ball to know who will do right by you and who will not. Therefore, you need checks and balances to protect you from the unknown. As I always say, “Trust but verify.”


If you provide the same level of access to your finances as Milano with her business manager, reviewing your investments and fees and understanding your inflows and outflows of cash and bill payments is very important. Stay on top of this.  


If this is beyond your control, please contact BrightLights for a free consultation.