After graduation, Simons returned to
Mashpee, Massachusetts and succeeded his maternal great-uncle
Watson F. Hammond as town clerk in 1915 and as tribal chief the upon his uncle's death the following year. He also had a small farm with a cow and requested a Carlisle student to work for him during the summer of 1915. Simons also served as Mashpee's tax collector, and he was appointed postmaster after petitioning for U.S. Mail service in Mashpee. He matriculated at
Suffolk University Law School in Boston in 1921 and graduated in 1925. At Suffolk he published an article in the 1921
Suffolk Register entitled, "Possibilities of Spare Moments." Simons was also a poet and published at least one poem in 1922 about Mashpee. Simon's sister Lillian, also was a published poet. As a tribal leader in 1928, Simons helped unite the Mashpee, Herring Pond, and Gay Head communities with their first joint
powwow. Simons purportedly left Mashpee around 1929, and his cousin,
Lorenzo Tandy Hammond, became the tribal leader, and for the rest of his life Simons lived around
Cambridge, Massachusetts working various jobs, including as a chaffeur, carpenter and janitor until his death in 1953. He was never married according to the 1950 U.S. Census. ==References==