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The time has come to reflect on the warning signs, decisions made, and repercussions of those in leadership of a financial services company which collapsed in the wake of the financial crisis during the mid-2000’s. The author was a divisional technology executive of this firm at the time, close enough to the top of the organization to observe the actions of those in charge. The author’s observations over a period of years eventually led her to resign from her position to enter a doctoral program only a few weeks before the company’s demise. The impetus behind the author’s resignation was her feeling that the decisions and actions of those in leadership violated her personal values. In this account, the author offers her personal reflections and the repercussions of this experience, followed by a deconstruction of this tragic leadership failure which includes references to the leadership literature.