TR was our first 'Progressive' President. Obama is just the latest. Churchill was a breathing human, but the similarity stops there.
I disagree and Churchill was a progressive in many ways just as TR was a conservative in many ways. But mostly it was the personality, the desire for glory, the fact that they could not be party-loyal, and that they were both prolific writers, the way they were brought up. You're mistaken if you believe that Churchill was a conservative.