In Massachusetts: 87 percent of teachers are white, while 47 percent of students are of color - a clear mismatch. Studies have shown that strong positive relationships are essential for learning, but often, the relationships between white teachers and students of color are strained at best, leading to poorer learning outcomes. Clearly, Job #1 is to diversify the teacher workforce, but research suggests that parity may not be reached for several decades. Educational leaders and policymakers must recognize and remedy the harm that many white teachers inadvertently cause. One lens for understanding this critical issue is to look at white teachers who have successfully crossed the racial/cultural divide. This interactive presentation will share the findings of a recent study of 19 white middle and high school teachers in Massachusetts who were deemed exemplary by educators and parents of color. We will discuss some of the changes that are needed to close the divide.