Here's what Teddy Roosevelt had to say about it, in his famous "New Nationalism" speech of 1910.
No man should receive a dollar unless that dollar has been fairly earned. Every dollar received should represent a dollar's worth of service rendered--not gambling in stocks, but service rendered. The really big fortune, the swollen fortune, by the mere fact of its size, acquires qualities which differentiate it in kind as well as in degree from what is possessed by men of relatively small means. Therefore, I believe in a graduated income tax on big fortunes, and in another tax which is far more easily collected and far more effective--a graduated inheritance tax on big fortunes, properly safeguarded against evasion, and increasing rapidly in amount with the size of the estate.And John McCain calls himself a Teddy Roosevelt Republican?


Historical context is needed. Teddy was a known trust-buster in a day of monopolistic enterprises.
What was Teddy chiefly for? Promoting free market competition. I think John McCain does alright there.
Also, it's important to note tax rates at the time. Teddy was speaking at a time when there was NO income tax. I'm not against taxes. I am against taxing over a third of a persons income. I think Teddy would be too.
I disagree. As the quote makes clear, he didn't want "swollen fortunes"--and was prepared to tax the hell out of them and spread the wealth around.
That raises the question - why didn't he?
He certainly had the support to do so as an extremely popular President with favorable majorities in both house and senate.
Nope, he was out of office when he made the speech in 1910.