- it is sponsored by a nonprofit that has been in existence for 5 years;
- no insider receives a direct or indirect pecuniary benefit other than participation on an equal basis with all other participants; and
- no person participates directly or indirectly in the management, sales or operation of the raffle other than the non-profit's employees and agents.
Deductibility of Ticket Price. A ticket purchaser has not made a deductible gift. The consideration pid is considered equal to the "chance" to win a prize therefore there is no disinterested gift and therefore no contribution deduction.
Non-profit's Obligation to Report Prize Income. The prizes are taxable income to the winners so the non-profit must ensure it properly reports the raffle prizes to the I.R.S. Generally, raffle prizes must be reported on Form W-2G with a copy to the winner if a) the amount paid, reduced by the amount the person paid for the chance to win a prize, is $600 or more; and b) the payout is at least 300 times the amount of the wager.
Non-profit's Obligation to Withhold from Prize Income. If the fair market value of winnings amount to more than $5,000, the non-profit must withhold taxes from the winnings and report this amount to the I.R.S. on Form W-2G. The non-profit is liable for any tax it fails to correctly withhold.
Back-up Witholding. If the prize is reportable (the amount paid, reduced by the amount the person paid for the chance to win a prize, is $600 or more; and b) the payout is at least 300 times the amount of the wager) and the winner fails to supply a taxpayer identification number, then the Foundation must withhold 31% of the total proceeds.
Federal Laws. Federal law strictly limits non-profits from conducting multi-state raffles. If the non-profit plans to use the U.S. mails for any part of the raffle – e.g. for mailing entry cards or raffle tickets – there are federal laws and regulations that bear consideration. Also, the FTC is empowered to regulated certain types of sweepstakes and contests.
Constructing a legal and compliant raffle takes time and may require the advice of a professional. Non-profits that take care to do it right will avoid embarrassing and costly legal mistakes and have a model that they can use to raise funds again and again.

Really interesting and worrying. I have posted a link to this on my blog and wonder if the same problem is happening outside the US. Hopefully there won't be many worthy charities hit by this.
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