This comparative study explores the experience of two first-year teachers in starkly different school systems, one in a small city on the northern plains and the other in a Midwest urban community. Using this comparative method, the authors looked at the similarities and differences of two different educational settings to collect data regarding the practices that best support first-year teachers. The individuals in this study are brothers, and both were employed as first-year teachers in middle school settings. Josh is an eighth grade social studies teacher in a small midwestern city with a population under 80,000, and Dan is a seventh grade English teacher employed in a large district in a Midwest metropolitan area of approximately 3 million. Josh observed the different experiences, strategies, and attitudes that existed over a three-day site visit at his brother's urban middle school. During this visit, he interviewed his brother regarding specific elements of support, as well as structural and conceptual approaches of the Midwest middle school. He also conducted several situational (informal) interviews with Dan's peers.