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Though laws vary slightly by jurisdiction, in general, a charitable pledge is considered a legally enforceable contract, experts say.
Mr. Redstone's declining personal fortune linked to the drop in the value of Viacom and CBS stock this year — he has little wealth outside his stakes in those companies — follows a large multiyear charitable pledge he made last year that became part of the dispute with his daughter.
Some donor-advised funds also now prohibit donors from using grants to honor a legally binding charitable pledge.
The rapper's random act of kindness is part of The Robin Hood Project, a charitable pledge he's taken to give away $1 million before Christmas.
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There's just one problem: charitable pledges are enforceable legal contracts.
Those with multiyear charitable pledges may want to seek an extension of their pledge, which is usually a legally enforceable contract, requiring agreement on any deferral.
There have also been questions about how much Mr. Trump has paid in taxes over the years, whether he in fact paid any federal taxes some years, and whether he has followed through on his charitable pledges.
Brian Byrd, who once worked for the Rockefeller Foundation and is now a lobbyist for arts groups, said that this year he interviewed for a job created to help review attendees to Mr. Clinton's annual conference and make sure charitable pledges were met.
It went to fulfill Huntsman's charitable pledges to Wharton, where he attended school, and to continue funding the Salt Lake City cancer institute that has his name on the door.
His Einhorn Family Charitable Trust pledged $50 million in 2014 to give all Cornell undergraduates exposure to hands-on practical learning experiences both in the U.S. and around the world.
Branson's numerous charitable initiatives included pledging an estimated $3 billion in 2006 to fund environmentally friendly fuel research.
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