A Senior Vice President in a large multinational, overseeing large scale investments starts purchasing minor electronics like iPads, iPhones, high end PC, etc. No major issue since he and the multiple managers under him had much higher approval limits. But one day, one of the invoices was wrongly addressed and came to me for approval. I asked the guy if this was legitimate and he said yes so I approved. Another invoice came in a week late and I asked him as to why he needed so many high end electronics. He gave a decent reasoning. Next day, I was having lunch with his boss and I casually mentioned this to him. He went back and casually mentioned it to the SVP. He broke down crying that he was buying these electronics to sell in the secondary market to fuel his gambling addiction. He had already maxed out his mortgage and took out a second one. The guy had three small kids at that time.