[1] Stein's father, Jerry Finkelstein, was the multi-millionaire publisher of the New York Law Journal, among other publications.

In 1977, Stein was elected as borough president of Manhattan, defeating Robert F. Wagner Jr. and New York City Clerk David Dinkins in the Democratic primary.

He was the Democratic nominee for Congress in the "Silk Stocking District" on Manhattan's East Side in 1984, but was defeated by incumbent Republican Bill Green.

In 1989, a decision by the United States Supreme Court declared the Board of Estimate was unconstitutional, in that it violated the principle of "one man, one vote", and a rewriting of the city charter called for the city council presidency to be abolished and the office of Public Advocate to be created as the presiding officer of the council and first in line of succession to the mayor.

[5] He pleaded guilty to a misdemeanor tax evasion charge and was sentenced to 500 hours of community service.