Set aside the standard list of reasons why Rudolph W. Giuliani – should he declare his candidacy – would find it challenging to secure the presidential nomination of the Republican party and then election to the White House in November of 2008. Instead focus on a factor largely overlooked: his sobriquet – America’s Mayor – is rooted in the urban history of the United States.

The standard obstacles confronting him are familiar enough and frequently recited. Giuliani has compiled a record that stands antithetical to the socially conservative ideology of the contemporary Republican party. He supports gun control legislation. He also is on record as being pro-choice on women’s reproductive issues. His skepticism about hardening regulations aimed at immigrants is well known. And he also espouses civil unions, but not marriage, of gays and lesbians. Giuliani subscribed to all of the foregoing positions during his terms as mayor, whether out of heartfelt conviction or a pragmatic acknowledgment of political reality in a dynamic urban polity. Traveling along the path leading up to 2008 might prove confounding for him. Should he suddenly resort to sublimating or sharply revising his well-articulated positions – instead highlighting his bona fides on national security as paramount – he might diminish his credibility under the glare of a hyper-intensive media frenzy.

A singular historical fact – of considerable magnitude -- also must be contemplated in considering the prospect of a Giuliani candidacy for presidency. Big-city mayors have found it perplexing in their efforts to achieve political traction when they have coveted higher office. During the course of the twentieth century no mayor – or former mayor – of New York City ever succeeded in attaining election to any other political office. Since 1950 three of the city’s mayors -- and former mayors – have been thwarted when they aspired to political advancement. Robert F. Wagner attained the nomination of his party for the United States Senate, only to be defeated in the general election. Nor could he attain nomination for mayor some years after he had retired from that office. John V. Lindsay was vanquished in his quest for nomination to United States Senate. Edward I. Koch, most recently, unsuccessfully pursued nomination for the governorship. Should Rudolph Giuliani attain the presidency in 2008 he will have to face down this longstanding record.

Add to this the fact that Grover Cleveland is the sole big-city mayor to serve as president of the United States, holding office for two non-consecutive terms (1885-1889 and 1893-1897). Previously he was the mayor of Buffalo and subsequently governor of New York. (Buffalo – population 155,00 – had ranked thirteenth among the nation’s cities in 1880, slightly behind Pittsburgh but ahead of Washington, D.C.) To be sure Calvin Coolidge was elected mayor of Northampton, Massachusetts in 1910 but that city hardly qualifies for big-city status! The most-recent big-city mayor to attain a presidential nomination was Vice President Hubert H. Humphrey in 1968, who in turn lost in the general election. He had served as the mayor of Minneapolis (1945-1949) prior to his election to the United States Senate in 1948. Richard G. Lugar, United States Senator from Indiana and previously mayor of Indianapolis (1968-1974), unsuccessfully sought the presidential nomination in 1996.

But very best way to understand the predicament of Rudolph Giuliani is rooted in the fact that American cities were entirely ignored – no visible mention whatsoever during the Constitutional Convention in Philadelphia – by the drafters. At that juncture roughly five percent of the nation’s population resided within its large cities. When the first federal census was conducted in 1790, New York City’s population totaled 33,000, having recently overtaken Philadelphia as the largest city in the new nation. (Chicago remained off in the future). Not that statistics alone explain this entirely. Well documented is the aversion of the founders to cities per se, which they regarded as fulcrums of political factionalism, unruliness, and rampant dissent. Well into the nineteenth century the nation’s cities, even as they confronted the large-scale transformations caused by the Industrial Revolution, found it virtually impossible to govern themselves. By the end of the century Chicago was regarded as the world’s shock city, its diverse population leapfrogging from a half-million in 1880, 1-million in 1890 (dislodging Philadelphia as the nation’s second largest city), 2-million in 1910, and 3-million in 1930. In the eyes of many Americans their biggest cities seemed politically untamed and culturally uproarious. A majority of the nation’s inhabitants resided in rural places rather than in cities until 1920. Walter Lippmann, the distinguished political commentator, claimed that Alfred E. Smith lost the presidential election of 1928 not on account of religion – the first Roman Catholic nominee – but as a consequence of his distinctly urban values.

Should Rudolph W. Giuliani eventually declare his candidacy for the Republican presidential nomination, a formidable obstacle that he would confront is embedded within his own political record that itself mirrors the narratives of American urban history.