When audiences first met Sam in the pilot, he was attending Stanford and getting ready to start law school. However, when his girlfriend Jessica was killed, the death set in motion Sam’s original journey to kill the demon that murdered Jessica.
The skills Sam picked up at Stanford did help when it came to doing research for hunts with Dean and other , so it wouldn’t have been too hard to get back into his studies.
Because of the pandemic, didn’t get the ending it deserved. This meant that viewers got minimal details about Sam’s life after Dean died in the . In Sam’s old age, the Impala can be seen under a sheet, implying that he stopped hunting. However, when Sam is on his deathbed, his son, Dean is shown having an anti-possession tattoo, hinting that hunting was still part of the family business.
Sam may have encouraged Dean to get the tattoo without ever letting him get involved in hunting, but it seems unlikely Dean would get a tattoo without knowing what it meant, or why he needed it.
With the series finale's mixed reception, one point of improvement would have been getting Sam Winchester the ending he deserved by shutting down the forever and removing himself completely from hunting. While it seems he got a few decades’ worth of time as a normal, non-hunting person, it seems as if hunting was never too far away from Sam’s life. Though an undeniably happy ending for Sam’s first-ever story, all things considered, it still would’ve been nice to see Sam and Dean Winchester retire together and leave hunting behind.
