Which do you think is more potent in a 1 vs. 1 situation (not against each other), Olaf's passive that gives him more ASP as he loses health combined with the new item, Maw of Malmortius, which increases how much damage he does each hit based on how much health he is missing, or Tryndamere with his combined passive and ultimate using the Maw of Malmortius to do massive amount of damage for about 5 seconds while Trynd turns immortal?
As scary as the Tryndamere is, you also have to remember that Olaf can use his W to gain up to 35 AD and 21% Lifesteal and Spellvamp, allowing him to stay alive as he hits you, possibly even longer than Trynd's Ulti can by itself. (Olaf's W lasts for 6 seconds and is on a 12 second cooldown, compared to Tryndamere's ~100 second cooldown).
Best Answer
I find that item to be not that good for Olaf because it punishes you for building HP. It scales off HP missing on percent, not total, so the more health you have, the harder it is to get its passive in the max.
For Tryndamere, it is a very good item because you should not build HP on Trynd, so he can make use of that item very well.