Two Arabic-speaking Jewish guards worked in the European Jewish agricultural colony of Petah Tikva soon after its founding, northeast of Jaffa, in 1878: Daud abu Yusuf from Baghdad and Yaʿqub bin Maymun Zirmati, a Maghribi Jew from Jaffa. The two men, who worked as traders among Bedouin but were recruited for a short time by the colony, offer a rare glimpse of contacts between Ashkenazi and Middle Eastern Jews in rural Jewish colonies established in the last quarter of the 19th century, colonies that are often regarded as detached from their local and Ottoman landscape. The article first argues that Zionist sources constructed these two men as bridges to the East in their roles as teachers of Arabic and perceived sources of legitimization for the European Jewish settlement project. It then reads beyond the sparse details offered in Ashkenazi Zionist sources to resituate these men in their broad imperial and regional context and argue that, contrary to the local Zionist accounts, the colony was in fact likely to have been marginal to these men's commercial and personal lives.