7 Bobby Singer Dies (Season 7, Episode 10)

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.

6 Dean Learns That Kevin Is Dead (Season 9, Episode 9)

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. Having lost both his brother and Kevin to Gadreel, Dean can't deal with his own guilt over what has just happened. Seeing him just quietly sit there, crying and uttering Kevin's name, shattered fans' hearts to pieces.

5 Eldon Murders Charlie (Season 10, Episode 21)

Сharlie Bradbury is a foster sister to Sam and Dean, so losing her after having lost so many others hits right where it hurts. In season 10, the Winchesters face the Stynes, who want the Book of the Damned back, and they are willing to do anything to get it.

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