The presidency that saw the greatest increase in wealth inequality
Pretty much whatever happens these next three odd years, the Obama presidency is going to be the most dramatic, accelerated rise of wealth inequality in American history (so far).
It's not Obama's fault. It's about the times, not about a person.
But when looking at history we did not live ourselves, we look at presidencies as summations of their times, and this one will make Reagan and Coolidge look like FDR. It will stand out as when the rich people really dug the spurs in... and despite the fact that the President is relatively to the left and does not actively support what is happening.
This stuff is not a result of Obama policies. Obama policies really are, compared to the opposition, relatively pro-worker and redistributionist.
But with some distance, people will probably look back at today with amazement at how low the bar of "pro-worker and redistributionist" was.
Corporate profits —up 20%/year since the crash.
Household wealth —up 1.5%/year since the crash
And restoring taxes to below where they were 10-15 years ago constitutes redistribution of wealth(!)
These are amazing times. Propose raising the minimum wage to $9.00 when historically it should already be $20.00, and you're a commie.
And with Romney or McCain the effects would have been even worse. No doubt about that. (Actually, the rich may get richer under Obama because the economy didn't completely collapse, which McCain would have ensured. Under McCain it would have been so bad that even the rich would have lost some ground, while the rest of us would have been digging our own graves.)
The point is the the entire political spectrum is, on matters of wealth, labor, wages, etc.., skewed so far to the right that sometimes we have to step back from the news-cycle politics to see the macro picture of our times, which is an astonishing explosion of wealth for the wealthiest no matter who is running things.
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years would be today ? I understand that you're trying to compare levels of progressiveness of our leaders and I'll grant you that, but different times call for different actions or responses. The issues of TR's day were not nearly as complex as they are today and let's try to keep in mind what type of Congress and opposition a President has to deal with.
As to who or what kind of people a President puts in his Cabinet..personally, I would want people with direct knowledge and experience to fill those posts.
TR never had to face the wealth and power the last several Presidents had to face...so, to me, comparisons are pretty much a matter of opinion. 
Obama is dealing w/ a very unique opposition, and let's keep in mind that "race" thing.
I think if Obama was white and he had rescued this country as he did, they'd already be talking about his place Mt Rushmore. 
Just imagine were the country would be if not for the forces against him.
I see him as a strong progressive working under very difficult circumstances...history will judge.
