How do ’warlords’ – defined in the Afghan context both by their military skills and capacity to strike a balance between local and external sources of support – respond when the war they are fighting ends? Why do some choose compliance with the new political order while others remain engaged in various forms of opposition? The political biographies of three longstanding warlords of the largely Pashtun southeast of Afghanistan – Mullah Rocketi, Qari Baba, and Jalaluddin Haqqani – enable us to explore the dynamics of quite different responses. The 2001 US-led intervention and the transitional challenges that followed led the three men in different directions. Rocketi took up a political career, was elected to parliament in 2005, and four years later remained an active player in legal politics. Qari Baba served briefly as a governor but was dethroned to the position of a security advisor and then assassinated. Haqqani stayed with the Taliban to become one of its most central commanders and by late 2009 led one of the major militant groups in the insurgency. Notwithstanding the considerable social and political similarities in the context where they operated and the challenges they faced, their personal trajectories diverged in the post-2001 period. This paper attempts to understand why this was so; why did one man lay down his arms to become a politician, another place his capacity for commanding violence at the service of the new Karzai government, while the third continued to challenge the new rulers with armed force? The analysis of these trajectories will provide an insight into the nature of violent warlordism during the formal transition from war to peace and into the post-conflict period.