At this point, I think Obama's about 31 superdelegates away from reaching 2025 once the last primaries run on June 3rd. However, as we're all aware, there's still the open issue of how to resolve the Florida and Michigan issue. Without getting into the same old issues of why or why not their delegations should be seated, let's look at what happens if they're seated as-is, with no penalties whatsoever.
First, let me do a little groundwork. I'm pulling the basic numbers for the scenario from Demconwatch - their scenario 5 (http://demconwatch.blogspot.com/2008/05/fl-mi-by-numbers.html)
For my delegate estimates for the remaining primaries, I used Slate's delegate calculator (http://www.slate.com/id/2185278/) It's only a rough estimate but that's good enough for these purposes.
I'm going to call a 40 pt victory for Clinton in Kentucky and a 10 pt victory for her in Puerto Rico. For Obama, I'm giving him 10 pt victories in Oregon, Montana and South Dakota. I'm also giving Obama the remaining 20 pledged delegates attached to Edwards. I think this is about as big a pro-Clinton spin on the numbers that we're likely to see. So what do we get?
For Obama we start with 1681.5 current pledged delegates. We add Edwards' 20 pledged delegates and another 86 pledged delegates from the remaining 5 contests and we get 1787.5 pledged delegates. (As a note, this is 50.1% of the total pledged delegates fwiw). Then we add the 305.5 superdelegates for a total of 2093 delegates. At this point, Obama is 116 delegates short of the 2209 threshold. He'd have to pull these from the 257 remaining superdelegates as well as the 55 uncommitted delegates from Michigan.
So, we're looking at getting 116 from 312 or 37.2%
Now, let's look at Clinton. We start with 1620.5 current pledged delegates. We add 103 pledged delegates from the remaining 5 contests and we get 1723.5 pledged delegates (48.3% of the total pledged delegates). Then we add the 288.5 superdelegates for a total of 2012 delegates. So, Clinton's 197 delegates short of 2209, or 63.1% of the remaining pool of 312 delegates.
Now, if we assume that it's fair to give Obama the 55 uncommitted delegates from Michigan, his delegate total climbs to 2148 or just 61 delegates short of 2209. He'd need just 23.7% of the remaining superdelegates to put him over the top.
Clinton would still be 197 delegates short, and she'd have a smaller pool to pull them from. She'd need 76.7% of the remaining 257 superdelegates to reach 2029.
So, even in the worst possible case for Obama, the math is still overwhelmingly in his favour.