You, might be able to deduct those expenses, though I've never seen it done. It requires to meet criteria which probably is pretty rare, since it's not "necessary":
Deducting entertainment expenses. | Legal > Tax Law from AllBusiness.com
Where are you coming up with this 28% figure that Uncle Sam is supposedly paying you for capital losses? As I said before, both short term gains and losses are taxes as ordinary income (whatever marginal rate you're at) but short term losses are taxed at the same reduced rate as gains with one downside caveat: You can only deduct losses equal to the amount of your gains plus $3,000 in the current year (the balance may be written off in future years up to the amount of gains plus $3,000). I know that very well as I helped a relative out with an investment and ended up with a large loss that will take me several more years to write off.