Phenomenon: As an impending shortage of primary care physicians is expected, understanding career trajectories of medical students will be useful in supporting interest in primary care fields and careers. The authors sought to characterize recent trends in primary care interest and career trajectories among medical students at an academic medical institution that did not have a family medicine department. Approach: Match data for 2,477 graduates who matched into resident training programs between 1989 and 2014 were analyzed to determine the proportion entering primary care residency programs. An online search and confirmatory phone call methodology was used to determine primary care career trajectories for the 795 graduates who matched into primary care residency programs between 1989 to 2010. Subanalyses were performed to characterize primary care career entrance among graduates who matched into the three primary care residency programs: Family Medicine, Categorical and Primary Care Internal Medicine, and Categorical and Primary Care Pediatrics. Findings: Between 1989 and 2014, 911 (37%) of all matched graduates matched into primary care residency programs. Of the 795 graduates who matched into these programs between 1989 and 2010, less than half (245; 31%) entered primary care careers. Of the graduates who ultimately entered primary care careers, 82% matched into either internal medicine or pediatrics residency programs and 18% matched into family medicine programs. Although there have been fluctuations in primary care interest that seem to parallel health care trends over the 26-year period, the overall percentage of graduates entering primary care residency programs and careers has remained fairly stable. Between 2006 and 2010, entrance into both primary care residency programs and primary care careers steadily increased. Despite this, the overall percentage of matched graduates who entered primary care careers over the 22-year study period (12%) was less than the national average (16%-18%). Insights: In the 26-year period between 1989 and 2014, primary care career interest increased slightly among medical students at this academic medical institution, with fluctuations that seem to coincide with national health care trends. Year-to-year fluctuations appear to be driven by rising numbers of Categorical Pediatrics and Categorical Internal Medicine matchers pursuing careers in primary care. There may be a need for specialized curricula and strategies to promote and retain interest in primary care at academic medical institutions, especially at institutions without family medicine training programs.