High levels of self-esteem and positive school, peer, and family connections represent protective factors against youth involvement in risky behavior. This paper reports findings from year one of the Healthy Kids Mentoring Program, a multidisciplinary mentoring program for fourth-grade students in a Midwestern public school. In October 2000, 28 fourth-grade students were admitted into the program, based on findings from a 55-item survey distributed to all fourth-grade students (N = 283) regarding overall self-esteem, school, peer, and family connectedness and involvement in risky behavior. The program, which ran from January 2000 to May 2000, consisted of four components: 1) relationship building, 2) self-esteem enhancement, 3) goal setting, 4) academic assistance. Pretest-Posttest data showed significant improvements at posttest in mentored students' self-esteem levels and positive connections to school, peers, and family. Mentored students also were significantly less likely to be depressed or involved in bullying and fighting at posttest than at pretest. Compared to nonmentored students, mentored students reported significantly higher school and family connectedness scores at posttest. Recommendations for effective mentoring program design are offered.