
Quoting
Taxing Matters
If he didn’t go as part of the work of the church (or any other charitable organization) then he has a problem. The expenses he paid for that trip are then personal expenses that would not have been deductible. If he then made the contribution to the church with the understanding that the church would use that money to reimburse himself for that trip then that contribution to the church is also not deductible. The money was not being used to fund the religious/charitable work of the church but instead he was using the church as a conduit to reimburse himself. In short he was trying to use the check to the church to try to transform the money he paid for a personal trip into a tax deductible expense. So it is critical here whether the primary reason for this trip and the expenses he incurred were to assist the church it its tax exempt activities or not. If not, I think none of it is deductible.