This question is so wide open because most boxing greats go out on a sad note,there have been only a few smart enough to walk away on a high note ( Lennox Lewis, Floyd Mayweather :shock::yep, etc. What legend was the hardest to watch going down, all of them is my answer but if I had to pick it would be De La Hoya.
For me it was seeing Leonard get smacked down at the hands of Camacho. I don't know why it bugs me more than his fight with Norris or Hoya's with Pacquaio. Maybe because I hold Leonard in the highest regard. Roy Jones Jr. at the hands of Calzaghe was very sad. I still can't believe that performance. He's still around but jeez...
Tyson, after the lewis fight. The "baddest man" on the planet, bloodied, beaten, the way he was apologetic and sincere in his interview. I really felt for him, it was hard for me to hold my emotions. I knew he was finished.
too many. but the way bobby chacon left the sport after all he gave to it including his lovely wife makes my sad and god knows were he is now most likely on the streets
leonard fighting camacho.. but in his prime, camacho wouldn't stand a hair's chance.. leonard would've whooped camacho's sorry-ass to oblivion though