A confrontation with a powerful municipal union was brewing even before Lindsay became mayor on January 1, 1966. The Transport Workers Union, which represented subway workers and bus drivers, was threatening to go on strike for higher wages. Lindsay, who had no experience with labor negotiations and lacked his predecessor’s close relationships with the city’s union leaders, had vowed to hold down city costs. He denounced Wagner’s private, albeit effective, negotiations with unions as a form of unsavory backroom dealing, and, although he himself met with the leadership secretly several times, he publicly refused to cut a deal with the union. TWU president Mike Quill retaliated by vocally taunting the mayor-elect. Well before inauguration day, Lindsay and Quill were adversaries, rather than partners, in negotiation.
Transit workers walked out on New Year’s Day – the day of Lindsay’s inauguration - in New York’s first city-wide transit strike since 1916. The strike did not end until 12 days later, when the Lindsay administration offered workers a generous wage and pension package, one that met virtually all the TWU demands. The increases cost twice as much as those in the previous agreement three years earlier. A poll showed that 75% of New Yorkers approved of Lindsay’s handling of the crisis. But the settlement cost the city at least $43 million over two years, foreshadowing a host of expensive future contracts with teachers, sanitation workers, policemen, and other municipal workers.