This essay analyzes the enacting of charity in The Merchant of Venice, with particular emphasis on moments of “double-gifting” in the plotlines of Portia and Antonio. Building on Henry Berger Jr.’s reading of the play in “Mercifixion in The Merchant of Venice,” I argue that both Bassanio’s wife and friend attempt to exert power over him by weaponizing unspoken obligations of reciprocity underlying their extravagant, repeated gifts of both self and property. Though Portia’s success at winning Bassanio’s fealty (as well as personal freedom for herself) contrasts sharply with Antonio’s near-complete loss of influence, a close reading of the ring plot and merry bond reveals a similar strategy of manipulation via charity behind the actions of both characters. I conclude by connecting the essay’s discussion of the play’s altered gift exchanges to the reality of emergent mercantile capitalism in early modern England, suggesting that said exchanges can be read as instances of “purchasing” interpersonal goods in a manner less explicit than, though bearing resemblance to, Shylock’s use of the money lending contract to obtain revenge on Antonio.