As established, the 1886 New York Mayoralty race was a three-way contest between political philosopher Henry George, representing the United Labor Party, Democrat Abram S. Hewitt, and Republican Theodore Roosevelt.

Henry George, for those unfamiliar, is described by Edmund Morris, in the chapter “The Next Mayor of New York” in his work The Rise of Theodore Roosevelt, as “the most powerful radical in America,” “famous as the author of Progress and Poverty (1879), one of those rare political documents which translate sophisticated social problems into language comprehensible to the ghetto.” (Morris, The Rise of Theodore Roosevelt, 339, 341). While labor parties running in past mayoral contests had not produced strong turnouts in the past, George announced that “if thirty thousand workingmen pledged to support him for Mayor, he would run on an independent Labor ticket. (Edward McGlynn – Catholic priest and social reformer—wrote in The North American Review’s “Lessons of the New York City Election” that “the best they hoped for was that an independent Labor candidate might get some 15,000 votes. For they sadly remember how, a few years ago, a Labor candidate for Mayor polled only 87 votes. They knew by experience how strong were the political organizations of New York, how potent the ‘influences’ on which these relied, and how general was the indisposition of men to ‘throw their votes away’ on a candidate who had not a ‘regular’ nomination.” (https://www.jstor.org/stable/25101145 - 575.)) Thirty-four thousand pledges flowed in, to the amazement of politicians all over the country.” (Morris, 341) While Morris also cites a figure of 15,000 votes as the most George could hope for, he mentions that when, upon his arrival in the city in early October, Roosevelt asked for the latest estimate of George’s voting strength, he was told “20,000, and probably much more” (Morris, 342). This outsized and unexpected success seems to have made traditional parties somewhat jumpy, with Roosevelt writing to his friend Henry Cabot Lodge several times in mid-October, saying:

“Many of the decent Republicans are panicky over George, whose canvass is not at all dangerous, being mainly wind; if the panic grows thousands of my supporters will go to Hewitt for fear George may be elected—a perfectly groundless emotion.” (Theodore Roosevelt to Henry Cabot Lodge. 1886-10-17)

“The Post and Harpers are working up the scare over him so effectively that undoubtedly thousands of my should-be supporters will leave me and vote for Hewitt to beat him.” (Theodore Roosevelt to Henry Cabot Lodge, 1886-10-20)

This potential run of voters to Hewitt is somewhat explained by Edward P. Kohn in his article, “A Necessary Defeat: Theodore Roosevelt and the New York Mayoral Election of 1886,” where he writes that the main fight of the election took place not between Republican and Democrat, or even between all three parties equally, but rather primarily between Democrats and the Labor party. “By the time Roosevelt officially accepted the nomination for mayor on October 15, only two weeks before the election, he had missed the momentum of the campaign. Reports of his nomination were overshadowed by a public debate between Hewitt and George appearing in the city’s newspapers. Indeed, George and Hewitt largely ignored Roosevelt’s candidacy, as did the city’s labor party press. By the end of Roosevelt’s first week as a candidate, even the New York Herald, which supported Hewitt, ignored Roosevelt and focused on George as Hewitt’s main opponent.” (Kohn, https://www.jstor.org/stable/23183358, 218-219)

It might be worth taking a quick look here at Roosevelt, who we know would later become, variously, Assistant Secretary of the Navy, Rough Rider, Vice President, and President of the United States. For all his future political success, Roosevelt at this time was still a young man who had just barely turned 28 by the time of the actual election. While he had several terms as a New York Assemblyman under his belt, he had been spending a great deal of time ranching in the badlands of western North Dakota, and had been out of formal politics for some time. He did not expect to be nominated as a candidate for the mayoralty, but when approached by party leaders was compelled to accept out of a sense of party loyalty.

Roosevelt seems to have ultimately viewed himself as a sort of sacrificial candidate, writing to his childhood friend Frances Theodora Dana that:

“I took the nomination with extreme reluctance, and only because the prominent party men fairly implored me. There is no chance of success (this you must be sure not to breathe as coming from me); the best I can hope for is to make a decent run; and the chances are even that my defeat will be overwhelming to a degree. The simple fact is that I had to play Curtius and leap into the gulf that was yawning before the Republican party; had the chances been better I would probably not have been asked.” (Theodore Roosevelt to Frances Theodora Dana, 1886-10-21 - https://www.theodorerooseveltcenter.org/Research/Digital-Library/Record?libID=o287291)

Morris fleshes this out a bit in his work, suggesting that one possibility that crossed Roosevelt’s mind was that “the party bosses had decided no Republican could win a three-way contest for the mayoralty and merely wanted a few thousand votes to trade on Election Day.” This is supported by a footnote in Elting Morison’s eight-volume The Letters of Theodore Roosevelt, where he writes of the 1886 election, “Tammany had sought out Hewitt to give prestige to the Democratic ticket. For a time Republican leaders considered supporting Hewitt, but partly in order to improve their future bargaining position with Tammany, they decided to present their own candidate. These leaders chose Roosevelt after Root and Levi P. Morton had refused to run.” (Morison, The Letters of Theodore Roosevelt, 110)

Kohn, for his part, endorses the idea of Roosevelt as a sacrificial candidate, but looks at the impact of his candidacy within the Republican party itself, rather than as a bargaining chip, writing, “By 1886, New York party leaders sought reform candidate who could stand as the nominee of a united Republican party, thus healing the split of 1884 that had cost Blaine the election. It was widely understood that any Republican nominee that year would be a "sacrifice candidate." During the election, Republican leaders continually stressed party unity with an eye toward the 1888 presidential election.” (Kohn, 208)

Finally, to address Abram S. Hewitt, the third of our three mayoral candidates and the ultimate victor, Edmund Morris describes Hewitt as:

“a man of mature years, vast wealth, moderate opinions, and impeccable breeding. Hewitt also happened to be an industrialist, famous for his enlightened attitude to labor (during the depression years 1873-78 he ran his steel works at a loss in order to safeguard the jobs of his employees.) He would doubtless attract all but the most extreme George followers, along with those Republicans who felt nervous about Roosevelt’s youth.” (Morris, Rise of Theodore Roosevelt, 343).

Although Hewitt may not be as familiar to us in the present day, he was a wealthy and well-known figure in New York society at this time. Continued next: