How did the title "political boss" come into the language?
The answer lies in our family history: Hugh McLaughlin was the boss of Brooklyn. Through his use of the title, “political boss” entered the political lexicon. He had been the boss of a work gang at the Brooklyn Navy Yard (a political job) before becoming the head of the Democratic party in the City of Brooklyn. He liked being called “boss” and continued the title after his elevation.
He used his influence to insure that he had a piece of the action when the Brooklyn Bridge was built. My grand grandmother (his sister?) was on the Brooklyn Bridge when it opened. he presided over the consolation of Brooklyn into Greater New York and did very nicely, thank you.
Hugh McLaughlin, the boss's father, was among those who organized the building of the first Catholic church in Brooklyn (St. James Cathedral.) The Brooklyn Eagle tells us, "On July 25, 1822, the cornerstone was laid for Brooklyn’s oldest Roman Catholic Church, St. James Cathedral-Basilica at 248 Jay Street." The boss's daughter married a Dr. Roach as reported in the New York Times on October 26, 1899: "MISS McLAUGHLIN WEDS.; Daughter of Hugh McLaughlin Becomes the Wife of Dr. James A. Roache of Brooklyn."
You can find a cartoon of his downfall on the internet. The Catholic Encyclopedia mentions him as one of the Diocese of Brooklyn's benefactors (perhaps it refers to his father).