Managing project risk is a key part of the successful implementation of any large project and is widely recognized as a best practice for public agencies to deliver infrastructures. The conventional method of identifying and evaluating project risks involves getting input from subject matter experts at risk workshops in the early phases of a project. As a project moves through its life cycle, these identified risks and their assessments evolve. Some risks are realized to become issues, some are mitigated, and some are retired as no longer important. Despite the value provided by conventional expert-based approaches, several challenges remain due to the time-consuming and expensive processes involved. Moreover, limited is known about how risks evolve from ex-ante to ex-post over time. How well does the project team identify and evaluate risks in the initial phase compared to what happens during project execution? Using historical data and artificial intelligence techniques, this study addressed these limitations by introducing a data-driven framework to identify risks automatically and to examine the quality of early risk registers and risk assessments. Risk registers from more than 70 U.S. major transportation projects form the input dataset. Firstly, the study reports a high degree of similarity between risk registers for different projects in the entire document of the risk register, and the probability and consequence of each risk item, suggesting that it is feasible to develop a common risk register. Secondly, the developed data-driven model for identifying common risks has a recall of over 66% and an F1 score of 0.59 for new projects, i.e., knowledge and experience of similar previous projects can help identify more than 66% of risks at the start. Thirdly, approximately 65% of ex-ante identified risks actually occur in projects and are mitigated, while more than 35% do not occur and are retired. The categorization of risk management styles illustrates that identifying risks early on is important, but it is not sufficient to achieve successful project delivery. During project execution, a project team demonstrating positive doer behavior (by actively monitoring and identifying risks) performed better. Finally, this study proposes using a data-driven approach to unify and summarize existing risk documents to create a comprehensive risk breakdown structure (RBS). Study results suggest that acquired knowledge from previous projects helps project teams and public agencies identify risks more effectively than starting from scratch using solely expert judgments.