He served as a law clerk at the old-line firm Alexander & Green.

[6] Simpson was one of the founding members of the "good government" organization the City Club of New York.

[2] In the early 1900s Simpson commissioned a bronze sculpture by Moses Jacob Ezekiel in the likeness of the blind poet Homer (accompanied by a student guide), as a gift for Amherst College, his alma mater.

[10] For reasons unknown the gift was refused, and Thomas Nelson Page, a University of Virginia alumnus who was active in his college's Alumni Association, stepped in to secure the gift of the statue to the University of Virginia instead.

[11] The final sculpture, entitled Blind Homer With His Student Guide, was completed in 1907, and is currently installed on The Lawn, in the grass to the north of Old Cabell Hall.