Timilty was known as "Diamond Jim" for his habit of wearing large diamonds, a reflection of his colorful public persona. Despite his tough reputation in politics, he was well liked within his community, often described as approachable and jovial, with a strong sense of camaraderie. Many in Roxbury viewed him as both a leader and a benefactor, known for securing jobs, housing, and welfare for his constituents. He retired from active politics after his defeat for the Governor's Council, though he remained a significant behind-the-scenes figure in Boston politics. Timilty died on July 6, 1921, at his summer home in
Sharon, Massachusetts, following a prolonged illness. He was survived by his five sons:
Joseph, Frank, Charles, Watler, and Harold. The James P. Timilty Middle School in Roxbury was named in his honor, reflecting his lasting impact on the community. However, in 2021, the
Boston School Committee voted to close the school as part of a district-wide phase-out of middle schools. ==See also==