Suppose you hold two series of options, both NQOs. Because of a big promotion, you expect your tax rate to increase from a current 31% to 39.6%. The current stock price is $70. The first set of options, close to maturity, has an exercise price of $25 and an estimated Black–Scholes option value of $48. The second set of options, with 5 years to maturity, has an exercise price of $50 and an estimated option value of $30. Should you exercise either series of options in advance of your big promotion?
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