[1] He was raised and educated in Essex Junction, where his father owned and operated the Bailey Granite Monument Company.

[5] During Bailey's presidency, the university undertook a large expansion and modernization program, including construction of several new buildings.

[1] He also worked to reduce expenses during the Great Depression, in addition to seeking scholarships and loans for students who needed them in order to remain in school during the economic downturn.

[1][6] After Bailey's death, university administrators discovered that the school had been operating with an annual budget deficit of more than $500,000, and he had used endowment funds to cover current expenses; as a result, his management of UVM's finances became the subject of negative press attention.

[1] This facility was expanded in 1980 and was known as the Bailey/Howe Library; David Howe was a 1914 graduate of UVM, and the longtime publisher of The Burlington Free Press.

[9] In February 2018 students and staff members protesting racism at the University of Vermont demanded that President Thomas Sullivan change the name of the Bailey/Howe Library because of Bailey's connection to eugenics.