Along with Bathhouse John Coughlin and Hinky Dink Kenna, Powers was considered one of the leaders of the "Gray Wolves" of Chicago politics.

After opening his own grocery store, he added a tavern next to it and used his exposure there to begin a political career as a ward captain.

Powers introduced the practice of distributing free turkeys, ducks, and geese to voters at Christmas,[5] but his inability to keep his ward clean of garbage or maintain the schools led Jane Addams to target him.

[6] Powers, in turn, used Addams's attacks on him to brand her as anti-Catholic, but he also hired her to be the ward's garbage inspector, the only paying job she ever held.

[4] Powers won the election, but the following year he returned to Chicago and was reelected to serve as the 19th ward alderman, a position he retained until 1927.