The gap between the trigger and the tax base is the whole design. Three times the base amount decides whether any of the payments count at all. Cross it and the entire change-contingent package becomes parachute payments, and the amount penalized is what exceeds one times the allocated base amount. That is a cliff, not a slope: an executive whose payments come to a dollar under three times their base amount owes nothing under section 4999, and one who crosses it by a dollar is taxed on a little over two years' worth of pay. Deal lawyers call the space just under the line the safe harbor, and payments are frequently cut back to stay inside it precisely because a small increase can cost far more than it delivers.
Who is exposed. A disqualified individual under section 280G(c) is a person who performs personal services for the corporation as an employee, independent contractor or other person specified in regulations, and who is an officer, a shareholder, or a highly compensated individual. The last of those is bounded: it reaches only someone in the group consisting of the highest paid 1 percent of the corporation's employees, or the highest paid 250 employees, whichever group is smaller. A personal service corporation is treated as an individual for this purpose, and all members of an affiliated group are treated as one corporation, with an officer of any member treated as an officer of the whole.
How the arithmetic is actually built. The base amount is the average annual compensation that was payable by the corporation and includible in the individual's gross income over the base period, or over so much of it as they worked there, so a recent hire has a smaller base amount and is easier to push over the line. Property transfers, including accelerated equity, are treated as payments at fair market value. Present value is computed using a discount rate of 120 percent of the applicable federal rate under section 1274(d), compounded semiannually. And the base amount is allocated across the payments in proportion to their present values, which is what makes each individual payment have its own excess.
Four ways payments come out of the calculation. First, the taxpayer may establish by clear and convincing evidence that part of a payment is reasonable compensation for services to be performed on or after the change, and that part is not a parachute payment at all. Second, reasonable compensation for services actually rendered before the change reduces the excess, and is offset first against the base amount. Third, payments to or from a qualified plan under section 401(a), a 403(a) annuity plan, a simplified employee pension or a SIMPLE retirement account are excluded outright. Fourth, and most useful in practice, section 280G(b)(5) exempts payments made by a small business corporation as defined in section 1361(b), read without its bar on nonresident alien shareholders, and payments by any other corporation whose stock was not readily tradable immediately before the change, provided the payments were approved by holders of more than 75 percent of the voting power after adequate disclosure of all material facts. That vote is why a private-company sale often comes with a 280G cleansing consent and a public one does not.
Two anti-avoidance rules worth knowing. A payment made under an agreement entered into within one year before the change, or under an amendment made in that window to an earlier agreement, is presumed to be contingent on the change, and the presumption can be overcome only by clear and convincing evidence. And a payment made under an agreement violating generally enforced securities laws or regulations is a parachute payment regardless of the three times test, though there the burden of proving the violation is on the government.
The separate securities-law layer. Since the Dodd-Frank Act, Exchange Act Rule 14a-21(c) requires a registrant soliciting shareholder approval of an acquisition, merger, consolidation or a proposed sale or other disposition of all or substantially all its assets to include a separate resolution, subject to a shareholder advisory vote, approving the golden parachute compensation disclosed under Item 402(t) of Regulation S-K, unless those arrangements have already been voted on at an annual meeting. The vote is advisory, so it does not stop a payment. It makes the numbers public and attributable, which is a different kind of constraint. Emerging growth companies are outside the requirement.