Trees often fail as a result of wind-induced stresses. During harsh storms, the branching mechanism plays an important role in the stress distribution and stability of trees subjected to such stresses. Eloy in PRL 2011, showed that Leonardo da Vinci’s original observation stating the total cross-section of branches is conserved across branching nodes is the optimal configuration for resisting wind-induced damage in rigid trees. The optimal branching pattern of trees and their tendency to break is a function of their reconfiguration capability and the process they employ to reduce high wind-induced hotspots. Through developing an efficient numerical simulation of rigid and flexible branched trees, the role of flexibility and branching patterns on stress mitigation and tree reconfigurations are studied. Our results show that the cross-sectional changes in the branching nodes, the overall tree geometry and flexibility play an important role in predicting tree breakage at each level of branching from the stem to the top branch. This study demonstrates that for a wide range of flexibility, an optimal branching law exists for both flexible and rigid trees wherein uniform stress distribution occurs throughout the height of the tree. For very flexible trees, the prediction of the optimal branching deviates from the aforementioned pattern and is greatly affected by tree reconfiguration. Acknowledgment: This work is supported by the National Science Foundation Grant Number CBET1943810