Joe Kennedy did make a lot on insider trading also smuggling bootleg whiskey into the states. The question as to why the Kennedys have all these millions when none of them have ever worked a day in their life goes back to all the investments old man Kennedy made & I’ve heard that because of Joe’s whiskey smuggling days that the Kennedys get a rake off on all the booze imported (legally) into America to this day.
As for why the Kennedy men are (were) notorious womanizers started with the old man. A woman understood or should have known that if you marry a Kennedy he’s going to cheat, it goes with the money & prestige you marry into.
There is a barest little bit of truth that lies at the bottom of this OP full of falsities:
Joe Kennedy foresaw the end of Prohibition (as did many people), but he took action and negotiated a deal to be the exclusive importer of various expensive brands of British & Scotch liquors, the deal to take effect upon repeal. So when that happened, he was ready to quickly begin importing big-name brands into the USA – a very profitable enterprise, especially at that time.
Of course, he was already rich from stock market investments. (And they were much more profitable than bootlegging would have been.)
As for profiting to this day, well, sort of. That importing company is still in business, and still making a profit, but the Kennedys sold their share of it long ago. But they invested the profits from that sale in other investments, so they are still making money off that to this day. Pretty much like anyone with inherited wealth.