A Canadian naval officer may have provided Russian intelligence officers with sensitive information related to an intelligence alliance among the United States, the United Kingdom, Canada, Australia, and New Zealand (Schmitt & Austen, 2012). If, indeed, this was done in an unauthorized manner and constitutes espionage or something related to it, what events may be associated with this event of interest? Initial candidates have included being a “very, very quiet guy,” “flew under the radar” in school, divorced, and financial problems (in 1998 “liabilities of $18,587 and assets of $1,000”; in 2010 debts on three credit cards and an outstanding loan), and slow progress for promotion in his military career. Are these even relevant in profiling espionage post-dictively? This chapter provides information to help answer this question.