The likelihood of him sustaining a double blow in the first injury round is slender, granted, so he's the big favourite to proceed to the final, as I see it - but winning the whole thing is a different matter. Should be possible to buy wisely here, and then ride your luck a bit.
The last part is what will ultimately decide this - and Downcast could simply get unlucky: He could lose A (huge player) and B (not too problematic) in the first injury round, which keeps him top of the pile for the s-f - but he now has to replace A somehow in order to look as good for a possible final. And then, in the second injury round, he loses C (another huge player). Suddenly, he isn't looking that sharp - and it all comes down to who he secures in the final reinforcement round (same as the rest of us).