than John ever was, as he is the one who basically raised them and was always there for them. In season 7, Dick Roman, the leader of the Leviathans, shoots Bobby into a state of coma, and the nostalgic episode hits viewers right in the feels.
Bobby's life is shown in the flashbacks, courtesy of the reaper, and Bobby himself is desperately trying to wake up long enough to get a vital message through to Sam and Dean. He manages to do it, calls them one last time, and passes away.
In season 9, another unexpected low blow comes to the Winchester brothers. Unaware that Gadreel is Metatron's ally, Dean allows him to possess Sam's body, which he uses to kill Kevin Tran, the Winchesters' longtime partner and friend.
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