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Although active offender research has shed light on perceptions of risk and potential success through criminal offending, few studies have examined the subjective perceptions formed around legal employment as an alternative to economic crime. Moreover, evaluation of relative risks and rewards of illegal and legal income generation have likely changed in the wake of diminishing employment opportunities, declining crime rates, and modern law enforcement strategies for disrupting drug markets. This study examines the subjective perceptions of legal employment and economic offending among 20 active and former drug sellers in Philadelphia during the Great Recession. It explores perceptions of and participation in legal and illegal work, views on whether drug selling is a viable career, noncriminal aspirations, and moral judgments about drug selling. Respondents articulated a strong desire to be part of the mainstream economy but saw declining opportunities to make a living wage through legal employment or drug sales alone. Several viewed drug selling and legal work as complementary strategies for making ends meet. Moreover, many perceived “the game” to be changing in unfavorable ways, particularly through the added risk posed by the “reckless” next generation of drug sellers. Most discussed desisting but had few concrete or realistic exit strategies.