AP attacks with War Mammoth equipped with Umezawa's Jitte. NAP blocks with two Merfolk of the Pearl Trident. AP assigns 1 damage to each merfolk and 1 to NAP (because trample). How many times does Umezawa's Jitte trigger?

Just once. The creature is dealing combat damage once (it's just dealing it to multiple creatures and/or players at the same time). Since it's dealing combat damage once, the Jitte will trigger one time and the Jitte will end up getting a total of two charge counters.

Nathan Long
Wizards.Com Boards NetRep