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Although the post-classical phenomenon of janissaries entering the marketplace has been well-known, we tend to imagine they engaged in businesses as individual soldiers and not as regiments. This paper tries to rethink this habitual idea by searching for economic activities by janissary regiments. My research in court records and central government’s edicts found some interesting cases that allude to the janissary regiments’ unfathomable and potentially large-scale economic activities. Seemingly the role of the regiments increased over the seventeenth century not only militarily and politically but also economically and commercially, given the frequency of their mention increased over time. In a situation where the government was drawing chronic deficits, the regiments may well have had to fend for themselves economically as well. Especially remarkable among their economic activities were regimental cash waqfs and (illicit) trade in highreturn commodities such as coffee and slaves. Most regiments seem to have had cash waqfs engaged in money lending, most commonly on a 15% interest rate with the borrower’s house as collateral; profits from commerce could be added to the waqf’s revenue. In the final section of the article, the possibility of high-ranking janissary officers’ involvement in such activities through their association with specific regiments is explored.