This is a practical, bold, no-holds barred look at challenges facing educational leaders and the university programs that prepare them through mid-century. It examines key continuities and discontinuities of current times for school, education, and society. Both practice and preparation occur in contested social space, the implications of which are explored in a post industrial, digital age.The stark warning signs of the conflict roiling educational leadership includes the re-segregation and marketization of the public schools; the demonization of teacher unions; attempts to de-professionalize professional preparation; the continuing achievement gap which ignores larger social inequalities; the debasement of education degrees by online diploma mills; the escalating culture of numbers and cheating scandals; and the erosion of full-time, seasoned faculty providing leadership to university preparation programs. The promise of social justice leadership anchored in a fast-changing demographic portrait of increasing national diversity is encapsulated in the construct of leadership accoutrement’s which awakens the art and science of leadership.. Finally, the authors propose the pedagogically centered leadership for creating a functional bridge between leadership and learning in preparation and practice.