This paper reports on the use of historically provocative artwork (i.e., artwork that challenges master narratives of history) created by Titus Kaphar and graduate students learning about leading with a socio-political consciousness about racism. The authors provided 17 students a series of prompts, based on Critical Race Theory (CRT) and critical art analysis, to instigate reflection, dialogue, and artistry in response to a painting by Kaphar. The authors organized participant-generated artwork into assemblages and crafted accompanying narratives which illustrated the inter/intra-changes among the components of the process and expressions: (1) compositionality, (2) aesthetics, (3) temporality, (4) historical injustice/oppressiveness, (5) manifestations of power. Thus, participants' artwork exposed how engaging with historically provocative can heighten socio-political complexities relating to the consciousness of race/ism and white(ness) supremacy.