Clear reductionist examples, but the 'evil' label isn't well-justified.<p>In the first 'evil' scenario (only Adam sells), it's only a bit unfair if Bill is contractually prevented from arranging his own private sale. Otherwise, he has the same freedom to arrange a person-to-person transaction as Adam does.<p>In the 'really evil' scenario (only Adam and Charles collect the dividend), it's only unfair if a vested Bill is prevented (by policy or secrecy) from participating in the dividend. That is, it's not the "dividend cash-out" tactic itself, but the exact implementing details, that <i>might</i> make it unfair. The blanket headline condemnation isn't supported.<p>Also, what if unlike in Salmon's scenarios, Bill has only a relatively small stake, and perhaps options that are only slightly in-the-money, or even still out-of-the-money? Bill might then actually assign a positive value to Adam retaining a controlling interest (versus later investors), or to the other benefits of a big jump in funding and company ambition.<p>If the dividend-to-others helps finesse that control/ambition equation, it could be more valuable to Bill's stake than a tiny amount of cash dividend now, or sparing him a tiny amount of extra dilution. The magnitudes and future hopes matter for an analysis of whether Bill would want to veto the deal or cheer it on. And if Bill (along with Adam and Charles) likes the deal when all factors are considered, can it be "evil"? No victim, no crime.