The Milwaukee Road is now little more than a memory in the collective American consciousness, but once it was a mighty engineering feat stretching from Illinois to the Pacific Northwest. The last major western transcontinental railroad constructed, the Milwaukee tackled tougher gradients and wilder terrain than any of its competitors, resulting in the added benefit to its passengers of fantastic mountain scenery. Operationally, however, scenery has its costs. The Milwaukee always looked at ways to improve operations, including electrifying portions of its Rocky Mountain and Cascade mountain range routes. It could be argued that the Pacific Extension should never have been built, that it doomed the railroad from the start with more route miles than it could ever maintain. However, the fact that the core system lasted until the 1985 takeover by the Soo Line is testament to the tenacity of the men and women who struggled day to day to get the trains over the road.
As is the case with many industries, personnel records generally have not been retained as historical documents by the railroads. The Milwaukee Road is no exception, and records that exist are in fragmented form. Some archival materials exist in libraries (such as the Milwaukee Public Library's Central Library), in archives (such as the Wisconsin State Historical Society in Madison), and in the collections of railfans throughout the country.
An example of the latter type of record is contained in the link below. Several years ago I came upon original copies of personnel change records for 8 employees of the Chicago, Milwaukee & St. Paul Railroad. Records are for such things as test results for engineer exams, establishing starting dates of service, results of eye exams. Mostly these are pretty routine, unless they happen to be ancestors of yours! I have posted JPG format graphic files of some of these documents. Some of the originals are slightly singed-I have the feeling someone pulled these out of a company bonfire! I haven't figured out anywhere else on the Internet to post these, so here they are.
Here is a listing of Milwaukee Road operating divisions as they existed in 1944.
The Milwaukee Road Archives were deposited in the 1980s with the Milwaukee County Federated Library System at the Milwaukee Central Library (814 W. Wisconsin Ave., Milwaukee, WI 53233-2385, (414) 286-3000). The holdings are large and are in the process of being organized by volunteers from the Milwaukee Road Historical Association. Much of the work to date has gone into stabilizing and cataloging blueprints, track diagrams, and photos. Among the photos that have been indexed are photos of individuals (such as group photos around locomotives, etc.).
There are some employee records and those that have been examined are indexed. They also have a complete set of the Milwaukee Railroad employee magazines, and have a last name index on-line. The collection is fantastic and library staff and volunteers have worked hard to make it all accessible.
There are boxes of materials that have not been explored yet, and more coming in from former railroaders and railfans, so it's hard to know what may turn up in the future. For more info and to browse the materials on-line, check the MPL site