Calgar. Although I might be bias (For Ultrama!!!!) Abaddon would win if he could get over his Daddy issues.
Err... I think you're talking about Horus. Unlike Horus, Abaddon has no Daddy issues, he's just purely bent on killing the false Emperor and any space marine or Xeno in his way.
Not really, although most people assume his 13 black crusades were fails, firstly most of the 12 other crusades actually succeeded in their objective as they were not aimed at the heart of the imperium, but rather they had other objectives that were accomplished and succeeded. The 13th Black crusade is ongoing, Abaddon still lives in Cadia waiting for reinforcements to drive them further into the imperium space.