What Happens to a Large, Uncashed Check When You Die?

Transcript of Podcast Episode 406

Hello, this is Bill Rainaldi, with another edition of Security Mutual’s SML Planning Minute. In today’s episode, we’re going to talk about an uncashed check, the resulting family dispute, and some important estate planning lessons.

There’s an old story about baseball legend Rickey Henderson that goes something like this. Early in his career, as a young, high-end prospect with the Oakland A’s, the team gave him a signing bonus of $1 million. Rickey had always dreamed of being a millionaire. So, when he got the check, he framed it and put it on his wall.

After a few months, the team’s accounting department reached out to him, wondering why he hadn’t deposited the check. Rickey later admitted that the story was, in fact, true.[1]

What would happen if you died with a large cashier’s check sitting in your house? That’s what happened not too long ago, and it turned into a huge legal battle between the surviving family members.

The story came to light recently with the estate of Bradley Haler, who died in 2021. Shortly before his death, Haler had visited his local bank and got a cashier’s check for $80,000, which was made payable to himself. But he died a month later, having never cashed the check.[2]

After he died, Haler’s wife Rebecca found the check and cashed it. She had been told that since the check had been written before her husband died, it was not part of his estate.

Bradley’s son from a different marriage, apparently the only other heir to his estate, had a different take. He believed that since the check remained uncashed at the time of his father’s death, it should be considered part of his estate, and thus, among the assets that would eventually pass to him; at least partially.

The parties ended up in court over all this. After a lower court ruled in favor of Rebecca, the Montana Supreme Court recently overturned that decision, ruling that since Bradley didn’t endorse the check or give it to Rebecca directly, it was still part of his estate.[3]

The lesson here is simple: don’t leave uncashed checks lying around! You never know what might happen.

But for Haler, the story gets worse. In addition to his $80,000 faux pas, he also died “intestate,” meaning that he died without a will.[4] Thus, regardless of how big or small his estate was, he ended up having no input over who would eventually get his money. We do not know the value of his estate.

Under Montana law, the spouse receives the first $150,000 of the estate plus half of the remaining assets, while his child would have received the rest.[5] We’ll never know if that was what Haler would have wanted.

He is certainly not alone. The majority of Americans die without a will.[6] It may not be something everybody thinks about, but being without a will can have a huge impact.

So, if you don’t have a will, where do you start? Some people have tried to save money by using an AI-based resource to draft their will. Doing so could certainly result in some short-term savings. But is it worth it in the long run? For one thing, an AI-generated will might not even be enforceable. Also, without someone there to ask follow-up questions, an AI-generated will may be unclear or inaccurate, causing some aggrieved heirs to challenge it in court.[7] For those reasons and others, using AI to draft your will is generally not recommended.[8]

Keep in mind that there are also some legitimate concerns about the confidentiality of anything generated by AI. Any information you enter into an AI model generally becomes part of their database, meaning once it’s there, it’s accessible by anyone searching, including other family members and their counsel.

To put it another way, you need to have a will first and foremost. But the stakes are too high to trust AI to write it for you. You need the help of a qualified estate planning attorney.

So, both Bradley Haler and Rickey Henderson made some rookie mistakes that could have been avoided. As far as Henderson goes, after the conversation with his team’s accountants, he eventually removed the check from his frame and deposited it into his account. He died in 2024 as a wealthy man. Haler never had that chance.

[1] Bates, Daniel. “Rickey Henderson’s Story Of Framing $1 Million Check Resurfaces After His Passing.” Thespun.com. https://thespun.com/mlb/rickey-hendersons-story-of-framing-1-million-check-resurfaces-after-his-passing (accessed September 25, 2026).

[2] Handler, David and Lothes, Alison. “Montana Supreme Court Finds Uncashed Check Includible in Decedent’s Estate.” Wealthmanagement.com. https://www.wealthmanagement.com/estate-planning/montana-supreme-court-finds-uncashed-check-includible-in-decedent-s-estate (accessed September 25, 2026).

[3] Id.

[4] FindLaw.com. “IN RE: the ESTATE OF: Bradley James HALER (2026).” Findlaw.com. https://caselaw.findlaw.com/court/mt-supreme-court/57873.html (accessed September 28, 2026).

[5] Id.

[6] Stone, Matt. “Cover Story: 76% of Americans die without a will.” WFMJ.com. https://www.wfmj.com/news/cover-story/cover-story-76-of-americans-die-without-a-will/article_9fd22853-7df4-582d-8f63-1eb9f66e0a58.html (accessed September 28, 2026).

[7] Id.

[8] Merryman, Ashley. “Can You Use AI to Write Your Will?” USNews.com. https://law.usnews.com/law-firms/advice/articles/can-you-use-ai-to-write-your-will (accessed September 28, 2026).

This podcast is brought to you by Security Mutual Life Insurance Company of New York, The Company That Cares^®. The content provided is intended for educational and informational purposes only. Information is provided in good faith. However, the Company makes no representation or warranty of any kind regarding the accuracy, reliability, or completeness of the information.

The information presented is designed to provide general information regarding the subject matter covered. It is not to serve as legal, tax or other financial advice related to individual situations, because each individual’s legal, tax and financial situation is different. Specific advice needs to be tailored to your situation. Therefore, please consult with your own attorney, tax professional and/or other advisors regarding your specific situation.

To help reach your goals, you need a skilled professional by your side. Contact your local Security Mutual life insurance advisor today. As part of the planning process, he or she will coordinate with your other advisors as needed to help you achieve your financial goals and objectives. For more information, visit us at SMLNY.com/SMLPodcast. If you’ve enjoyed this podcast, tell your friends about it. And be sure to give us a five-star review. And check us out on LinkedIn, YouTube and Twitter. Thanks for listening, and we’ll talk to you next time.

Tax laws are complex and subject to change. The information presented is based on current interpretation of the laws. Neither Security Mutual nor its agents are permitted to provide tax or legal advice.

The applicability of any strategy discussed is dependent upon the particular facts and circumstances. Results may vary, and products and services discussed may not be appropriate for all situations. Each person’s needs, objectives and financial circumstances are different, and must be reviewed and analyzed independently. We encourage individuals to seek personalized advice from a qualified Security Mutual life insurance advisor regarding their personal needs, objectives, and financial circumstances. Insurance products are issued by Security Mutual Life Insurance Company of New York, Binghamton, New York. Product availability and features may vary by state.​