The tour comes as Trump’s campaign has been investing its own money to make inroads with black voters and erode Democrats’ overwhelming advantage with them. But the cash giveaways are organized under the auspices of an outside charity, the Urban Revitalization Coalition, permitting donors to remain anonymous and make tax-deductible contributions.

The organizers say the events are run by the book and intended to promote economic development in inner cities. But the group behind the cash giveaways is registered as a 501(c)3 charitable organization. One leading legal expert on nonprofit law said the arrangement raises questions about the group’s tax-exempt status, because it does not appear to be vetting the recipients of its money for legitimate charitable need.