WI Henry George or Teddy Roosevelt was Mayor of NYC

The Mayoral Election of 1886 in New York, a three way race, was an interesting one, known mostly for the two candidates who didn't win: Henry George, Labor Candidate who came in second, and Teddy Roosevelt, who came in third.

What if one of them had won? Assume the winner (unlike Hewitt) serves two terms (which would last through 1890, by my reckoning)?
 

Japhy

Banned
Being as TR came in Third its more probable that Henry George would be the winner. That though, brings up a number of potential events, as the largest city in the United States is now run by what at the time is a radical political movement, right in the middle of the Guided Age.

From the viewpoint of the City itself, a radical left party in power is something that could theoretically push the reform minded City Republicans into the arms of Tammany, rather then United Labor. I doubt such a political alliance could last past the 1898 unification of the City but for a decade we could have a rapport between the two parties on Manhattan, one Brooklyn is voting in the same elections we'll see the Republicans begin to move back towards their Proto-LaGuardianism.

As far as administration goes, George and his clique are the leadership of United Labor, but the rank and file of the party came from Trade Unionists and the Urban Poor, there is going to be as soon as the new mayor is sworn in a crisis in the party as Marxists try to expand their influence. That said we can probably see common ground on a few issues, like laws that work to keep Asians out.

Beyond that, I'm not sure how George's theories would be attempted, or how he'll be able to deal with the combined might of the old Conkling Machine, Tammany, not to mention Federal and State governments. More later on that.

As for Teddy Roosevelt, he's going to need a miracle to be a winner here. In New York City the Democrats were on the rise, the GOP wouldn't be viable until the rise of Fusion tickets in the next decade, and wouldn't be able to stand on their own in New York City until well into the Next Century. The Republicans knew this too, and that's why such a young, relatively inexperienced candidate was even the nominee.
 

Japhy

Banned
Of course one has to deal with Voter Fraud to have George win, but its much easier to do if the Catholic Church doesn't stand against the United Labor Party.
 
Thought I'd post here rather than start a new thread:

TR was also pressed real hard to run in 1894, a year the Republicans did win the office. So if he ran and won, what kind of mayor would Roosevelt be? Would his impact at the local level be anything like his time as Police Commissioner OTL?
 
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