The authors examined the association between weight patterns during middle age and incident type 2 diabetes mellitus using a subset (n = 1,476) of the Framingham Heart Study original cohort limited-access data set (1948–2003). Participants diagnosed with diabetes before age 50 years were excluded. A functional principal components analysis of body mass index from age 40 years to age 50 years was used to define weight patterns in terms of overall weight status (normal weight, overweight, or obese), weight change (weight loss, stable weight, or weight gain), and weight cycling. Overall overweight and obesity were associated with higher rates of diabetes (for overall overweight, crude hazard ratio (HR) = 3.2, 95% confidence interval (CI): 2.3, 4.6; for overall obesity, crude HR = 8.8, 95% CI: 6.0, 12.8). Weight cycling was also associated with higher rates of diabetes (crude HR = 1.6, 95% CI: 1.2, 2.1). Neither weight loss nor weight gain was associated with incident diabetes. After adjustment for overall weight status, weight cycling was no longer associated with higher rates of diabetes. This study underscores the importance of obesity in diabetes risk and the importance of preventing the development of overweight and obesity earlier in life.