This article undertakes a retrospective appraisal of Nigeria's widely acclaimed, yet contentious, success in its interventionist role in Liberia and its seeming inability to contain the threats posed by members of the dreaded Islamist militant: Jamaa'tu Ahlis Sunna Lidda'awati Wal Jihad/al-Wilyat al-Islmiyya Gharb Afrqiyyah, also known as Boko Haram. Drawing references from scholarly articles, electronic channels, and other commissioned reports, the article explains why Nigeria appears to be losing the war against Boko Haram, in contrast to its modest strides in Liberia between 1990 and 1997. We argue that Nigeria's inability to contain the Boko Haram insurgency can be located within the context of its home-grown systemic challenges; particularly, its ineffectual political leadership and the politicisation of its national security under the Goodluck Jonathan Presidency.