2014 Air Force calendar. A free gift for volunteering at the Smithsonian. I put it on Freecycle and made someone pretty happy.
Gaming headphones with microphone. The Chief Engineer got these for $40 and then his brother sent him a better set as a holiday gift. We sold this pair on ebay for $38, so we only lost $2.
This file folder I bought right out of college when I was just starting out learning about finances etc. I now use binders to keep my finances organized and this thing never helped me anyways. Cost: $10. It went in the trash, as my office already has many of these and no one uses them.
Baskets for the aerogarden I used to have. It was impossible to clean, used a lot of energy, and didn't really produce much to eat. These probably cost $5. Sold them on ebay for the amount of money it cost to ship them. Also, judging by the strange name of the "organization" that ordered them, I realize I may have sold them to a marijuana dealer. Can't be sure though.
Total money wasted: $17
Total money wasted on stuff I never should've bought: $2368