The inflation-adjusted tax rates in 1955:
(via http://www.taxfoundation.org/taxdata/show/151.html)
Look at that! Even if you discount the rates as too high, look at where those bracket thresholds were! In 1955, out of 24 tax brackets, 16 of them affected incomes above the equivalent of $250K for married couples filing jointly. Kind of makes the "is $250K 'rich'?" point moot: it's more than some, less than others, obviously, and we used to treat it that way.
What was he saying about a failed ideology that never worked anywhere in the world? Except "the free world" apparently. (I guess we were "socialists" back then. Imagine how embarrassed the Soviets must have been!)
I guess learning the difference between mixed economies and Stalinist police states is one of those things you learn in college that's too eggheaded for someone who bills $250 million.
And just for kicks, here's a graph of the inflation-adjusted tax bracket thresholds for the last 60 years (It's easy to find charts of the top rate, but tougher to find clear displays about where the burden fell in the past. And remember, this chart doesn't deal with what the rates were, just the breakpoints where one level of income was treated differently from another):
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