Although the literature base is replete with ideas about how to develop and support rich social studies teaching, advocates have been unable to show a consistently positive effect. Good history teachers take no single shape. Grant (2003, 2005) suggests that it is the interplay of teachers' deep subject matter knowledge, knowledge of their students, and the challenging contexts they teach in which makes them ambitious teachers. In this article, based on Grant's framework, we describe four cases of ambitious history teaching using big ideas. The principal question driving the project was: How are ambitious teachers making use of big ideas to teach history? Initial findings suggest that ambitious teaching is no panacea; it is challenging, nuanced, and highly-contextualized work. Using big ideas to frame one's practice allows for richer and more complex subject matter, more varied teaching and assessment approaches, and more consideration of the interests and abilities that all students bring to class. At the same time, ambitious teachers must navigate a rocky road, one that includes the need to seize control of the curriculum, come to terms with the evolutionary nature of one's teaching practice, and respond to administrative realities. The ambitious teaching examples in this article add to the history education literature that demonstrates the kind of teaching that is possible in schools under real and perceived constraints.