now since the loss of Ace(R.I.P) all three of the HST have officialy lost someone important. first one is Ichigos mother who was tragically killed by the hollow named grand fisher. the reason i bring this up first is because he was the first to lose someone officially sure naruto never knew his parents same for luffy but they were ok without them anyways but ichigo was the most affected by the death of his beloved mother who died saving him(sorry no pictures of her death so im just gonna put one of her) what happened in his life had its pros and cons. its pros were that he became a badass fighter and sub shinigami but the cons were that he became an emo biz-natch but u know whatever we still love strawberry boy :)
now Narutos loss, Jariya(or whatever remember not a naruto fan just doing his out of respect lol) Jariyas death was tragic to naruto because he was basically like a father to him, a perv father but his perv father non the less lol his death wasn't as tragic because naruto didn't have to see it first hand in front of him but he still was depressed by this but it was not life altering since he knew he had to become stronger for him as well but it was a sad day for him and others(got the vid for this :O
read this spoiler ONLY IF U HAVE WATCHED ONE PIECE UP TO DATE!!!!
so which one do u consider saddest? iOne Piece? Naruto? Bleach? go ahead and chat it up(im getting depressed talking about this and want to go into a corner and cry ;( jk kinda but i wanted to share)