[2][3] Once he reached voting age, Maynard joined the Hendricks Club, where was a lieutenant of Martin Lomasney.

[3] From 1910 to 1914, Maynard, backed by Lomasney, James Michael Curley, and John F. Fitzgerald, served as president of the Boston Democratic Committee.

[7][8] In 1933, Maynard was appointed Collector of Customs for the Port of Boston by his close, personal friend Franklin D. Roosevelt.

[9] In addition to his duties as Collector, Maynard was also a trustee of the Norfolk County Agricultural School from 1934 to 1938.

Deputy Collector Owen McKenna, who was accompanying Maynard, stopped to consult a doctor.