Conversation so far:
Did Frank Hague commit any questionable acts?
Yes, he took kickbacks in cash, and relied on two ordinances of dubious constitutionality to muzzle critics
Did Frank Hague do anything illegal?
He passed an unconstitutional ordinance that gave himself as commissioner the power to turn down permits for meetings if he felt it necessary to prevent riots, disturbances or disorderly assemblage.“
Did anyone attempt to prosecute Frank Hague?
Yes, but he was also able to avoid prosecution despite numerous federal and state investigations in part due to the fact he took most of his kickbacks in cash.

Question: In what way was he Boss of Jersey City?
Self-contained rewrite: In what way was Frank Hague the Boss of Jersey City?