This article argues that risk is central in (re)producing the unaccountable commercial military/security markets that are a normal part of our political reality. The argument is twofold: first it is suggested that risk rationalities and the associated ‘preventive imperative’ has a depoliticising effect – accentuated by the impersonal spread of risk rationalities and the strategies of risk professionals – which lowers the eagerness to seek accountability. However, and second, depoliticisation is significant above all as a serious obstacle to the innovative thinking that is the sine qua non of effective accountability. The enmeshed, ‘hybrid’, nature of the market places it in the ‘blind spot’ of law and is as such fundamental to the current lack of accountability. Consequently, moving beyond established regulatory frameworks and technical understandings of accountability (that is, politicising the market) is a precondition for more effective accountability. Failing to do so, will leave the current rapid legal innovation impotent while reinforcing impunity as the focus on and confidence in established regulatory frameworks grows. The failure to politicise creates an ‘accountability paradox’ where the pursuit of accountability diminishes it. The article develops this argument with reference to Blackwater's (now Xe) role in the so called CIA ‘Killing Program’.