In 2022, a year marked by high-profile deaths, leaders worldwide expressed their condolences for the passing of Mr. Shinzo Abe, Queen Elizabeth II, and Pope Benedict XVI. This study primarily compares the condolence strategies employed to honor these distinguished figures. An analysis of the deceased individuals naturally revealed some significant differences, such as their role, gender, cause of death, and length of reign or term as a leader. This study investigates how these differences influenced the choice of condolence strategies. The dataset comprises 150 official statements, including letters and Twitter messages, written in English by world leaders, with 50 messages dedicated to each deceased individual released to the public shortly after their passing. A modified coding scheme, focusing on linguistic realizations, was applied to perform the relevant analysis on these official condolence communications. While there were a variety of condolence strategies used for the three deceased individuals, direct strategies prevailed over indirect strategies, with slight variations among sub-strategies. Among the direct sub-strategies, the use of an address term, was the most commonly utilized. Differences in role, cause of death, and length of reign or term as leader contributed to the choice of condolence strategy made by well-wishers, while gender did not.