Except that the Hague Machine was a lot more recent than Tammany Hall, about the 1930's.
When my parents went to work in the same corporation (where my mother finally landed), they had college degrees and were given jobs that required non-Jews to have only high school degrees. This was before WWII and they both said things improved after the War.
My maternal great uncle started (with a partner) the Restaurant Workers Union, as it was called then, back in the day. So, what you're describing wasn't a union universal and it's also possible that since yours wasn't Italian, he couldn't get mobbed up and was held back because of that.
My paternal grandfather was a career low level Jewish gangster, his arrests made the newspapers a few times, but that's a story for another day.