Between 1969 and 1970, The Weather Underground Organization (WUO) was the most violent avant-garde among the North-American white radical movements. Not only its rhetoric, but also its first (attempted) actions clearly proved the group’s willingness to engage in anti-personnel violence. However, despite the initial trajectory, the WUO, in less than one year, disengaged from murderous violence and opted for demonstrative violence. As a matter of fact, in the following seven years of activity, the organization targeted only property and avoided hurting people. Such a change of strategy has been conventionally attributed to the shocking episode in which three of the WUO members blew themselves up while assembling an explosive device. Surprisingly, all the other factors – at micro, meso and macro levels – that could have potentially contributed to making those individuals more likely to de-escalate still remain unexamined. Therefore, in this research I suggest that this case of “early disengagement” deserves more scrutiny. To fully address this question, I propose, first, to interpret de-escalation of violent repertoires as a multifaceted and interactive process that calls for a longitudinal analysis. Second, I employ the Weathermen’s accounts to grasp the factors that drew those people toward a different path. With this end in mind, I examine a set of interviews personally conducted with ten members of the WUO. In the paper I demonstrate that the interviewees consistently underrated the challenges of the clandestine lifestyle and the threat of repression. I further examine the way they overlooked the psychological effects of carrying out deadly attacks and their moral consequences. Finally, I indicate that they tended to stress the strategic concerns and the importance of the out-group context. Even though generalizing from such a small sample might be premature, interesting findings emerge and they can be valuable for scholars building theories of disengagement.