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How to gift money anonymously to an individual after collection thru a donation site?
You mention that "A great friend and couple's family" which makes me think this is a couple.   For gift tax concerns, you can give a couple 2 x the gift tax exemption ($28,000 in 2015).  Your example of $22k would fit in this amount. To give this money anonymously, I know that people have reached out to a pastor in the area who will deliver an envelope with the gift and not disclose the source. Talking to a pastor who has done this, he said the call came out of the blue and he was happy to be able to help.