Both Richard Dudley Sears and Herbert Moon Sears were sons of Frederick Richard Sears
born 20 Apr 1824 in Boston, Suffolk, Massachusetts and his second wife Albertina H Shelton 1834 - 1915
Herbert Maron Sears Birth Date: 12 Nov 1867 Boston and died 1942
Father Name: Frederick R Shelton - Mother Albertina Shelton
http://www.searsr.com/richard1/pafg170.htmhttps://familysearch.org/pal:/MM9.1.1/N4HX-PT51870 Boston Ward 6, Suffolk, Massachusetts
Frederick Sears 46 and Albertina Sears 35
Marion Sears 17 Frederic Sears 15 Lina Sears 11
Richard Sears 8 Philip Sears 2 Herbert Sears 2
The marriage 2 June 1891 gives his middle name as Mason (Herbert Mason Sears) Caroline was born Sep 1870 in ,Massachusetts. She died 17 Jan 1908 in Regis Hotel, New York.
https://familysearch.org/pal:/MM9.1.1/N4HX-Q381900 Census -
https://familysearch.org/pal:/MM9.1.1/M9Y8-KVLReference Phyllis Sears (daughter of Herbert and Caroline) on the 1900 Census - Phylllis Sears to Wed - Boston $2,000,000 Heiress Engaged to Bayard Tuckerman, Jr. (Miss Sears is a daughter of Herbert Mason Sears and a granddaughter of ... She is an expert tennis player, all excellent skater, and is well known for her riding.
There is an obituary for the daughter of Phyllis Sears Tuckerman - Phyllis (Tilly) T. Cutler
It sounds as if she had a passion for tennis and golf.
http://www.salemnews.com/obituaries/x712198101/Phyllis-T-Cutler/printUnder Segis in 1920 -
https://familysearch.org/pal:/MM9.1.1/MF9Z-V4GHarvard Univ directory 1910 graduate with twin brother
Richard Dudley Sears - 16 Oct 1861 - 8 April 1943
Graduate Harvard Univ [c1879-83 ] 1910 directory-232 Beacon St, Boston
US National Tennis Champion 1881-7
http://en.wikipedia.org/wiki/Richard_Sears_(tennis)
Younger brother Phillip Sears was consistently in the top ten ranking for five years; and his cousin, Eleo Sears, was inducted to the Tennis Hall of Fame.
http://www.sportspundit.com/tennis/players/6392-richard-searsSandra