Last modified on Thu 22 Apr 2021 02.56 EDT It was during the administration of Fiorello LaGuardia that the position of New York City mayor became known as the âsecond toughest job in Americaâ. LaGuardia, New Yorkâs 99th mayor and a man whose name now graces the cityâs streets, parks, schools and an airport labeled one of the worst in the country, became regarded as one of the cityâs greatest ever leaders, despite facing a collapsing economy, all-powerful crime mobs and civic unrest when he took office in January 1934. When New York Cityâs next mayor takes office, however, they will face problems on perhaps an even larger scale, with the Covid-19 pandemic having ravaged a city already beset by deep income inequality and facing a reckoning over racial discrimination in policing and governance. The job could prove, once again, to be second only in difficulty to being the occupant of the Oval Office.