One of the standout recurring villains of the Kripke era is Gordon Walker, portrayed by the excellent Sterling K. Brown, who had a severe hatred for Sam Winchester and died as the very thing he spent his life hunting; a vampire.
Gordon could have been a fantastic return in the show had he appeared in Purgatory to oppose Dean, but his staying dead is not bad.
Many , partly due to how disappointing and tame the Leviathans led by Dick Roman were.
After getting killed at the hands of Cas and Dean - subsequently sending them to Purgatory - Dick was never seen in the series again, not even in Purgatory when Cas and Dean got there. It is hard to imagine Dick adding much to the series by coming back, especially with Purgatory already offering a good amount of interesting content, so it was probably for the best that he never returned.
From victim to a friend to lover to prisoner to an enemy, Anna Milton underwent quite the character arc in which ended at the hands of Michael, who destroyed the angel for attempting to kill the Winchester's parents.
Outside of Castiel, angels returning from the dead or appearing in the show after their deaths were few and far between.
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