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My mother-in-law withdrew all the money she had in the bank in September 2015. This month September 2020 marks 5 years since that happened. She gave my husband half and my brother in law half of the money. Checks weren’t deposited until October. Would that be an issue if she was to apply for Medicaid on October 1st.? I’m wondering if the timing is just too close for comfort. What date counts the date the check was written or when the check was deposited into someone else’s account? Thanks in advance for any thoughts and ideas on this.

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I would wait if at all possible until November if you (she) could, just to be safe. If she does apply in Oct, it's possible to be an issue, but its going to depend on the dates the Medicaid case worker requests for the bank statements and how aggressive they are in your State. If they ask for your husband's bank statements, they likely will ask for Oct 2015, and thus would see the deposit.
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In our experience, Medicaid will look at the date the money was taken from your mother in law's account, not the date the check was written. (You definitely want to check my opinion with a lawyer familiar with the Medicaid rules in your state.)

They will not ask for your husband's accounts. Pull your mother in law's October, 2015 statement and make your decision from there. If she applies on October 1, 2020 and money left her account after October 1, 2015 you'll need to explain it or accept the penalty.
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