The federal tax code, at least, is already massively progressive, and the rich pay far above their share of the revenue already.
Not to mention Bezos and other billionaires keep getting richer even with a ʾmassively progressive' tax code. It's not progressive enough!
1) The wealthy have the resources to fight back against much higher taxation and play the long game. Even if a spate of progressive candidates are elected and drastically raise taxes, the wealthy will just wait until the political pendulum swings back and will get themselves a better deal than they had originally.
2) Even if higher taxes on the wealthy stuck, there is not nearly enough money there to fund every progressive pipe dream (education, healthcare, housing, environment, inequality, reparations, etc, etc). So once again, the working middle class gets stuck with the tax bill, just like every other time we’ve tried something like this.
And speaking about conservatives sounding outdated, there’s nothing that highlights the naivete of youth more than hearing them say “this time it’s different”.
The current progressive plan being floated on the left (socialist is a scare word cooked up in the 1950s and still bandied about by conservatives who have no clue how outdated it makes them sound to younger voters) is to greatly increase taxes on the rich and use it to fund social services like college. So, by your own logic, this can work.