[2] After serving in World War II, Winkelman entered the insurance business.
[3] After City Councilman John M. McDevitt resigned his seat to enter the priesthood, Democratic ward leaders in Northeast Philadelphia's 10th district selected Winkelman to run for the seat in a 1962 special election.
He was successful, retaining the seat for the Democrats and defeating Republican Joseph Leo McGlynn, Jr.[4] After taking his seat, Winkelman was assigned to chair the Labor and Civil Service Committee.
[7] He remained active in politics and ran again for council in 1967, losing in the primary despite support from the party hierarchy.
[8] After the death of Francis R. Smith in December 1967, Winkelman was elected to succeed him as leader of the 58th ward.