He was employed for several years by the Mitchell Brothers Company, a land agent firm in several states, dealing with large tracts of timber for making lumber.

Caldwell was Republican member of the Michigan State House of Representatives for two terms, from 1897 through 1900.

[2] Caldwell was employed by the Mitchell Brothers Company, buying and selling timber lands.

[1] Caldwell and his older brother Thomas, were some of the earliest settlers in Missaukee County.

[1] Caldwell was a member of National Grange of the Order of Patrons of Husbandry[1] and had a successful diversified system of farming.