Large American cities lose 50%-70% of beginning teachers in 4-6 years, the attrition rate of pre-service teachers is 20%, baby boomers are retiring in unprecedented numbers, and the teacher satisfaction survey (MetLife, 2010) indicates that one-third of those teachers remaining in the workforce plan to leave soon. Furthermore, the cost of teacher attrition to the American economy now exceeds $2.2 billion dollars annually (Keighler, 2010). These factors, among others, contribute to the U.S.’s teaching/teacher education “crisis” (NCTAF, 2003). The yearly replacement of one-third of the country’s teachers, mostly by newcomers, is an inadequate approach to meeting societal demands (Ingersoll, 2004). Also, alternate forms of teacher certification/evaluation and value-added approaches to accountability are not working (Ravitch, 2011). While Americans agree that teacher education is vital to students’ academic performance and the country’s economic status, they are rancorously divided as to what the next steps should be (Levine, 1996). This paper presents the U.S. teacher attrition and retention literature, along with cases of teachers from different regions who exited early and later in their careers. This field work makes visible the swarm of factors surrounding teachers abandoning their careers and the complexities underlying the American teacher attrition and retention phenomenon.