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An expense is deductible only if Congress (in the case of federal taxes) has passed a law saying it is deductible. Otherwise it is not deductible.

Now, Congress cannot anticipate everything. It passed laws saying that "ordinary and necessary" expenses in generating taxable income are deductible. Is a two week trip to a luxury resort in Hawaii ordinary and necessary? So the IRS writes some regulations to explain in greater detail what might or might not be ordinary or necessary. Did the IRS exceed its authority or make unreasonable regulations? That's what the courts are there to decide.

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