This paper examines how the varying elements of patronage, plunder and power became enmeshed in Sir John Hippisley's ventures during the 1620s. It is clear that Hippisley's privateering activities were profitable. The lieutenancy of Dover Castle provided a steady income from 1625 to 1628, while the sale of that office to Sir Edward Dering brought with it something of a "windfall" profit, especially as Hippisley had apparently received it as a free gift from Buckingham. Indeed, Hippisley's dispute with the judge of the high court of admiralty, which was partly overlaid by the ancient hostility between the admiralty and the Cinque Ports, suggests that Buckingham's wide network of patronage was based on a delicate balance of negotiation between potentially rival interests. As this system grew in size, and as it was subject to growing pressure as a consequence of the wars with Spain and France, so it became increasingly difficult to maintain a balance between these different interests.