James Michael Curley

Curley's father was a foot soldier for democrat ward boss James 'pea-jacket' Maguire; at the time the ward boss system acted as a mafia style organiser for the cities corruption.
Curley’s political carrier began in local politics where he promised progressive policies to help the poor; Where he founded the “Tammany Club” as a political group named after the “Tammany Hall” group – while continuing to present himself as oppose to the machine.
As part of his rise to power, Curley used a New York Times report on political corruption to present himself as opposed to the establishment’s vices.
In 1904 - Curley and the unrelated Tomas Curley helped two people cheat postmen exams; this led to both a rise in his popularity with Irish voters as well as a fraud conviction he served time for.
Curley planned to run for mayor in 1910, however incumbent John "Honey Fitz" Fitzgerald convinced him not to run for mayor and instead run in the next term unopposed – between these elections he joined congress; In his campaign Curley used the gimmick of sending his friend to walk on the streets asking "where's the honest man?".
In the 1914 election Fitzgerald broke his rule and ran again with the backing of the ward bosses. Honey Fitz did eventually withdraw when Curley blackmailed him with evidence of his affair with a cigarette girl named Elizabeth "Toodles" Ryan.
In Curley’s first term, he builds hospitals and social homes with funding from threatening banks to loan him money.
In 1918 he loses the election avoiding the molasses disaster.
Then the following term in 1921 he wins again - in part by spreading rumours that his opponent wasn't truly Catholic; he also staged fake KKK attacks to emphasise his points about anti Irish racism
In 1930 he won a 3rd non-consecutive term.
In 1932 after being denied a space at the DNC he pretended to be a delegate from Puerto Rico named Alcalde Jaime Curleo.
After being term limited he becomes governor for a bit.
the term limits where then repealed and in 1946 he won a 4th term.
Later that year he got arrested for war corruption (investigated by Harry S Truman) but shortly after got let out due to poor health and was allowed to return to city hall.