Distracted driving behavior is a perennial safety concern that affects not only the vehicle’s occupants but other road users as well. Distraction is typically caused by engagement in secondary tasks and activities such as manipulating objects and passenger interaction, among many others. This study provides an in-depth analysis of the increased crash/near-crash risk associated with different secondary tasks using the largest real-world naturalistic driving dataset (SHRP2 Naturalistic Driving Study). Several statistical and data-mining techniques were developed to analyze the distracted driving and crash risk. First, a bivariate probit model was constructed to investigate the relationship between engagement in a secondary task and the safety-critical events likelihood. Subsequently, two different techniques were implemented to quantify the increased crash/near-crash risk because of involvement in a particular secondary task. The first technique used the baseline-category logits model to estimate the increased crash risk in terms of conditional odds ratios. The second technique used the a priori association rule mining algorithm to reveal the risk associated with each secondary task in terms of support, confidence, and lift indexes. The results indicate that reaching for objects, manipulating objects, reading, and cell phone texting are the highest crash risk factors among various secondary tasks. Recognizing the effect of different secondary tasks on traffic safety in a real-world environment helps legislators enact laws that reduce crashes resulting from distracted driving, as well as enabling government officials to make informed decisions about the allocation of available resources to reduce roadway crashes and improve traffic safety.