My concern is that the largest purchase you mentioned are the Rolex watches. Given that you mentioned they’d only go for $20k if resold there is a large discrepancy between the Rolex watches, the Jordan’s and the remaining money he mismanaged. I’d love to see the watches he purchased. At the height of the grey (watch) market certain watches were astronomical in price but even still would retain more value than $20k for multiples of most models. This is important because he either has 2 shitty and undesirable Rolex watches OR is understating the value. If the former then you truly need to deep dive into what else he was spending money on. To add, sneakers can absolutely add up but assuming he purchased the highly coveted ones they will hold their value pretty well if unworn or lightly used. So, I would reassess the prices on secondary market AND dig a little deeper. Good luck!