In 1881, Truesdale accepted a job as traffic manager of the Chicago, St. Paul, Minneapolis and Omaha Railway and later became vice president.

Following a brief tenure in this role, Truesdale served as the first vice president and general manager of the Chicago, Rock Island and Pacific Railroad, a position he kept through the last decade of the 19th century.

[3] He immediately cemented his reputation as a relentless visionary by launching one of the most ambitious railroad modernization programs in American history.

Until the dawn of the twentieth century, the DL&W — like most railroads dealing with adverse geography — generally followed the contours of the land when laying track.

Built to replace the DL&W's "Old Road", this enormous construction project involved huge amounts of cut and fill through the Pequest Valley of northwest New Jersey.

[6] DL&W launched its Phoebe Snow marketing campaign, one of the best-known in American advertising, in 1902, shortly after Truesdale became president.

[7] In his obituary, the New York Times described him as "a militant, hard-hitting and hard-working champion of the railroads against the constantly increasing demands of legislators and labor leaders alike.