Guy buys an expensive (+/- $15k) piece of medical equipment in 2019. No insurance coverage to pay for it. Clearly deductible as a medical expense, even though it's a capital expenditure under the usual rules. See reg. 1.213-1(e)(1)(iii). But he was a high income guy and got no tax benefit from that expense. Comes 2020 and guess what - the equipment gets destroyed in a fire in the small shed where he kept it when it was not in use. And his homeowners insurance did not cover it. It was worth $12k when the fire happened. His 2020 income will be way lower than 2019's.
He asked me what tax benefit he could get from this second event. I'm not sure if there's any at all.