If Sarah, a CEO of a large investment company, has a gross taxable income of $31,000,000 and her itemized deduction is $50,000, while her standard deduction is $4,500, which deduction can she take? She can take both amounts as deductions. She can't take the one which is the smaller amount, which in this case is the standard deduction. She can take one of them, whichever is the greater amount and in this case, she would take the itemized deduction. She can only take the standard deduction, as a itemized isn't used if you're in the highest tax bracket