[3][9] He received his education at Williams College (graduated 1890) and Harvard Law School (entered September 22, 1890; left 1892).

[3] Holden practiced law as a partner in Dean, McLeod & Holden in Kansas City; it was his work in this company as a local attorney for the Great Northern Railway during the Minnesota Rate Cases before the Supreme Court that influenced James J. Hill in his favor.

[2][3] In 1907, Holden left private law practice to become the general attorney for CB&Q, where his first assignments were to manage the railroad's interstate commerce litigation.

[3] When World War I began and American railroads were brought under the control of the United States Railroad Administration (USRA), Holden was asked to head the USRA but declined the top position, opting instead to assist incumbent director William Gibbs McAdoo.

[3] Since the Southern Pacific management team was based in New York, Holden also maintained an apartment there at 610 Park Avenue in addition to his home in Chicago.