Simpson served two terms as a Chicago alderman for the 44th Ward, from 1971 through 1979. Simpson has (both during and subsequent to his city council tenure) been considered to be a progressive. In the redistricting that took place before the 1971 election, the 44th ward was redrawn to include less of the heavily
Jewish and politically independent lakefront, and to include more of the heavily Democratic areas to the west, making it a harder district for Simpson to win as an independent than it had been for Singer to win as an independent. Kargman was the son of a politically-connected
Cook County Circuit Court judge. Simpson was supported by lakefront liberal voters. He ran on a platform that advocated for community control of municipal programs such as
urban renewal. Community groups of the 44th ward were in the midst of a dispute with the city over urban renewal at the time of the election. Simpson was reelected alderman in 1975, again defeating an opponent supported by the city's Democratic Party organization, Edward Marsalek. The Committee for an Effective City Council, a group founded to support the election of "independent" candidates to the Chicago City Council, endorsed him and twelve other aldermanic candidates (including fellow incumbents
William Cousins,
Anna Langford, and
John Hoellen) on the same day that Pucinksi withdrew. He was supported by the lakefront liberals. During his time on the City Council, Simpson was a critic of
Richard J. Daley. After he was elected alderman in February 1971, alderman-elect Simpson endorsed Daley's
Republican-nominated opponent Richard Friedman in the
1971 Chicago mayoral election (for which the general election was held in April). Despite being nominated by the Republican Party, Friedman was politically a political-reform minded
independent Democrat with roots in the
Better Government Association, and was similarly endorsed by
Jesse Jackson. In once instance, Simpson angered Daley so severely that Daley attempted to have the City Council's
sergeant at arms force Simpson back into his seat. Simpson became the leader of the minority bloc of independents on the Chicago City Council. As such, he came into conflict with
Michael Bilandic, first during Bilandic's stint as Daley's floor leader on the City Council, and later when Bilandic took office as mayor after Daley's death in office. Like with Daley, he frequently stood in strong opposition to Bilandic during Bilandic's mayoralty. Being in the minority opposition to mayors Daley and Bilandic, Simpson's proposed legislation were usually defeated. The resolution, which Simpson had feared would have little chance of passing, was passed on June 26, 1974, in a unanimous 44–0 vote after it was amended by Daley-aligned alderman
Paul Wigoda. The investigation was later ended by a Chicago City Council vote of 40–3 in April 1978 to accept the investigative committee's majority report over the minority report written by Simpson, Lathrop, and Oberman as investigative committee members. While few wholesale pieces of legislation authored by Simpson were passed, Simpson saw occasional success in making amendments to legislation. The council debated taking action against the towing company. In March 1977, Simpson and fellow aldermen
Dennis H. Block, Ross Lathrop, Martin Oberman proposed a piece of legislation that would have established community
zoning boards in each of the 50 wards of the city. Simpson established a "ward assembly" for the 44th Ward. Decades after Simpson left the council, journalist and news editor
Bruce Dold remarked,
Retirement from the City Council Simpson opted against seeking reelection in 1979. He endorsed independent candidate Bruce Young, the director of the Jane Addams Center at
Hull House, to succeed him. Young pledged, as a candidate, to support existing legislation and ordinances that Simpson had proposed on issues such as redlining, the creation of a code hearing bureau, starting an independent
audit of the city's finances, and the establishment of a commission on governmental integrity. Young's opponent was John McCaffrey, who had the backing of the city's Democratic Party. Young won the election, but resigned soon after taking office, citing "personal reasons". ==Post-aldermanic career==