John Lindsay was a three-term Republican member of the House of Representatives from New York from 1959-1965 and then mayor of New York City for two terms from 1966-1973. His years as mayor were beset by turmoil, as he governed through major strikes from the city’s transportation and teachers’ unions, as well as precipitous rises in both crime and the city’s budget deficit. Criticism of Lindsay by conservatives began during his Congressional career, when he often sided with Congressional Democrats in support of John F. Kennedy’s initiatives, most notably the imposition of more robust ethics rules for Congressional legislators. During his mayoral years, Lindsay’s vocal anti-Vietnam war activism and his struggle to balance the city’s budget brought him more criticism, especially from conservative members of his party. As a result, he became a Democrat in 1971.
During Lindsay’s tenure as mayor, New York City’s debt rose from $2.5 billion to $9 billion, and his efforts to balance the budget through tax increases (most notably a 1966 increase in the city’s income tax rates) seems the likely inspiration for these poster stamps. In addition to the "Dump Lindsay" slogan appearing at the bottom of each one, the silhouette features the words "I Am the Mayor" underneath it, and is surrounding by a ribbon repetitively featuring the word "tax." The silhouette is wearing a laurel wreath, meant to caricature Lindsay as a Caesarian dictator. Intriguingly, these stamps were found in Group Research, Inc.’s folder of ephemera collected from Ronald Reagan’s headquarters at the 1968 Republican National Convention. Their association with Reagan in 1968 suggests an eye towards national political issues even as Reagan was only one year into his first elected position as governor of California.