19He keeps getting resurrected
This is a common problem for pretty much every major character on Supernatural, especially the core trio of Sam, Dean, and Castiel. These three boys have been through Hell (literally, multiple times) during the series' run, and that has meant that they've each bitten the bullet multiple times.
Sam's count rests somewhere
around seven. It's hard to be exact because it's hard to tell which events count as him actually perishing (for instance, does his soul simply passing through Hell count in and of itself?) but Sam has gotten resurrected every time, without fail. Whether by an angel or some other force, Sam has perished and been brought back so many times that fans have to wonder if the stakes of the show could ever be real.