As it relates to the return addressess of the covers #1 and #3, here are biographical sketches of the two attorneys named (bios are dated 1909).
Interestingly, Albert D. Bosson, was Mayor of Chelsea, Massachusetts (1891) and both lawyers were at one point apparently in partnership with each other during the period in which these covers were postmarked:
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BOSSON, Albert Davis, lawyer; b. Chelsea, Mass., Nov. 8. 1853; s. George C. and Mary Jane (Hood) B.; A.B., 1875, A.M., 1878. Brown Univ.; studied law In offices of Brooks, Ball & Storey. Boston, and in Boston Univ. Law Sch.; admitted to Suffolk bar, 1878; m. Chelsea, May 18, 1887, Alice Lavinia Campbell. Associated in practice with Charles E. Grinnell, 1878-91; sp'l Justice Police Court of Chelsea, 1882-92, Justice since 1892; mayor of Chelsea, 1891. Mem. Boston Bar Assn.. N. E. Historlc-Geneal. Soc., S.R. Clubs: University, Mass. Reform. Residence: Chelsea, Mass. Office: 722 Tremont Bldg., Boston.
WHITTLESEY, Henry Lincoln, lawyer; b. Chelsea, Mass., Nov. 30, 1862; s. Corydon M. and Maria L. (Ayer) W.; 7th In descent from John W., Saybrook, Conn.; grad. Yale, 1884; studied law with Richard H. Dana, Boston; LL.B., Harvard Law Sch., 1886; admitted to bar, 1886; m. Newton, Mass., July 6, 1889, Lillian Eddy, lineal descendant on mother's side of Edward Winslow, Mayflower pilgrim. Began practice in Boston, 1886; In partnership with Judge Albert D. Bosson, 1888-92, now Whittlesey & Wales; mem. Newton City Council. 1896; alderman, 1898, 1899; elk. Newton Police Court, 1890-1903. Cong'list. Club: Boston City. Residence: Newton, Mass. Office: 743 Tremont St., Boston.
ALBERT D. BOSSON (Image and Bio related to his term as Mayor of Chelsea, Massachusetts):
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ALBERT D. BOSSON, seventeenth mayor, born in Chelsea, November 8, 1853, he is decended from a long line of patriotic New England ancestry. His four great grandfathers served in the Revolution and his grandfather, John D. Bosson, was one of the early settlers of Winnisimmet village took an active part in the War of 1812. At age fifteen he graduated from Chelsea High School and entered Philips-Exerter Academy. He was a graduate of Brown University in 1875 and Boston University in 1877. In 1882 he was appointed associate justice of the Chelsea Court. He was elected the first democratic mayor in the year 1891. While mayor he advocated and was instrumental securing the abolishment of grade crossings between Chelsea and Charlestown. He was the first to advocate the overhead bridge to Charlestown. He was the first to recommend improvements to Winnisimmet Square and an advocate of the Metropolitan Park system. Governor Russell appointed him judge of the Chelsea Court in 1893.
In 1887 he married Alice Campbell the daughter of C. A. Campbell. They had two children, Campbell Bosson, born November 18,1888 and Pauline Arland Bosson, born February 24, 1894. Albert Bosson died on April 6, 1926.