Risky decision-making is affected by past feedback, especially after encountering the beneficial loss in the past decision-making round, yet little is known about the mechanism accounting for the distinctive decision-making that different individuals may make under the past loss context. We extracted decision functional medial frontal negative (MFN) and the cortical thickness (CT) from multi-modality electroencephalography (EEG) and T1-weighted structural MRI (sMRI) datasets to assess the individual risky decision under the past loss context. First, concerning the MFN, the low-risk group (LRG) exhibits larger MFN amplitude and longer reaction time than the high-risk group (HRG) when making risky decisions under the loss context. Subsequently, the sMRI analysis reveals a greater CT in the left anterior insula (AI) for HRG compared with LRG, and a greater CT in AI is associated with a high level of impulsivity, driving individuals to make risky choices under the past loss context. Furthermore, for all participants, the corresponding risky decision behavior could be exactly predicted as a correlation coefficient of 0.523 was acquired, and the classification by combing the MFN amplitude and the CT of the left AI also achieves an accuracy of 90.48% to differentiate the two groups. This study may offer new insight into understanding the mechanism that accounts for the inter-individual variability of risky decisions under the loss context and denotes new indices for the prediction of the risky participants.