The 1886 mayoral election of New York City provided a fitting conclusion to a year of unprecedented activity by organized labor. Henry George represented the United Labor Party (ULP) in an intense campaign that garnered national attention. Though George did not win the election, he outperformed every other candidate ever fielded by organized labor in NYC and earned more votes than the Republican candidate, Theodore Roosevelt. This presentation will explore the origins of George’s candidacy and the larger significance of the campaign in the context of Gilded Age politics. The 1886 mayoral contest provides an opportunity to reexamine the extent of George’s popularity among the working class and the potential benefits of land value taxation in the nation’s most densely populated urban center.