I personally think sometime after Sam left for Stanford. Sam Winchester and Dean Winchester Oh my pudding shirt Sam is surprised to hear that Dean goes on solo hunts, so that’s something he hasn’t done when Sam was around. Solo hunts mean Dean would need his own vehicle, so John probably gave him the Impala and got himself that GMC truck he was driving. Dean was looking out for him pretty much and made sure Sam was always fine. He only went back to hunting because Dean came for help to find John and then his fiance got murdered by yellow eyes. Once that happened he became self-destructive with the demon blood and thinking it was the right way even though it really wasn’t. Dean on the other hand was always somewhat self-destructive in his early to late teen years. With flashbacks, we see he was a womanizer even as he got older he stayed the same.
View product: Sam and Dean Winchester Oh my pudding Supernatural shirt
Sam Winchester and Dean Winchester Oh my pudding shirt, sweater, hoodie, and ladies tee
Best Sam Winchester and Dean Winchester Oh my pudding shirt
As he aged he went to booze because who wouldn’t after Sam Winchester and Dean Winchester Oh my pudding shirt dealing with everything he had to deal with. He knew he was Sam’s only hope and as a big brother, he felt he was responsible for Sam because their dad was never around. He didn’t want to leave Sam alone, john was always gone so sam would have been alone. Dean coped by knowing he was there to take care of Sam and watch out for his little brother and protect him no matter what because that’s what John asked him to do. Dean is and always has been afraid of disappointing his dad so he made sure he didn’t. Sam coped knowing he had a plan on getting out of the hunting business and doing his life differently than his dads and brothers.