One interesting question is whether the money given to organizations who are running Chinese auctions or raffles counts as tzedakah for Maaser purposes. For US tax purposes purchasing a lottery ticket or a raffle ticket is not tax deductible.

<p><span style="color: #222222; font-family: arial, sans-serif; font-size: 12.8px;">The Sefer&nbsp;Tzedaka Umishpat &nbsp;argues if you win the&nbsp;</span><span class="il" style="color: #222222; font-family: arial, sans-serif; font-size: 12.8px;">raffle</span><span style="color: #222222; font-family: arial, sans-serif; font-size: 12.8px;">&nbsp;it does not count as a donation. &nbsp;This is true particularly if you would have spent the money anyways on the item received. If you don't win it all counts as maaser</span></p>