This article investigates the distribution of equity ownership between entr
enched management and dispersed outsiders when management has the ability t
o manipulate the cash flows and when it is costly for equity holders to pro
ve managerial wrongdoing in court, Management chooses the distribution of e
quity ownership so as to maximize private benefits against the risk of pote
ntial control challenges. When shareholders are long-term oriented, then ou
tside shares trade at a premium over their value to management, and managem
ent is inclined to sell off its equity stake to dispersed outsiders. When s
hareholders are short-term oriented, then outside shares trade at a discoun
t below their value to management, and disciplinary pressure can be substan
tially reduced via strategic share purchases. Changes in the cost of capita
l drive a wedge between entrenched management's and dispersed outsider's va
luation of shares, Management exercises its option to buy (sell) shares whe
n the option is in the money: when management values shares more (less) tha
n outsiders do.