The position of "Police Chief" was first held by Daniel F. Wolff, who was appointed in 1908. His appointment over Capt. William Lent, brought such censure on the administration that newspapers reported it as one of the major reasons for the defeat of Mayor Warren by Mayor Lennon in 1910. During the campaign of that period, Democrats made an issue of Wolffs appointment and promised that if elected, they would effect his removal and name a successor from within the department. Lennon was elected and did oust Wolff but the ouster was carried to court and Chief Wolff won not only reinstatement, but back pay as well. Again, when William J. Wallin was elected Mayor, widespread rumors repeated that Wolff would be removed. Instead, his authority was extended beyond that of the previous administration. Wolff was constantly opposed on the grounds that he had no prior police experience, among other things. He had served as a Captain during the Spanish American War, a post he rose to from private. When he took office as Police Chief, he said he would put the department on a military basis. One of his requirements was that his men practice marching on their own time.
Chief Wolff abruptly and unexpectedly retired on a disability pension on March 12, 1918. His disability pension became effective in May 1918 at $3,300 a year. Wolff died of a heart attack at age 68 on September 14, 1933 at his home at 15 Caryl Avenue. The office of Chief of Police was to remain vacant until Sept. 1,1926.