I think by the time S3 rolled around, Sam could take Dean, but probably *wouldn't*, for a lot of reasons.
Psychologically, I'm not sure what it would take for him to really take John down, were John still alive. As angry!young!man! as S1 Sam was, he still couldn't shoot him when he needed to (not lethally, anyway). And that's a gun -- physical contact is much more intimate.
I'm sure I'm overthinking this. Surprise!
Was it as late as when Dean was lying on the floor telling him if he walked out the door, not to come back, echoing Sir's words.
He was juiced up on demon blood then, though, wasn't he? I don't think we've seen them scuffle since then. The last beatdown, after Veritas, RoboSam just took it. And I'm pretty sure RoboSam could whup Dean's ass.
I still think John could take them both still, even if I waver on which of the brothers would win. I can think of guys with similar size differences where both train and the smaller one would win, but we now have a Sam with much less hesitation than he used to.
I just think John has none.
I think in a dead even "fair fight" Sam would win against Dean. When both are fast and strong and skilled, muscle and mass are decisive. But give Dean some tiny advantage he can use to leverage his greater experience and cunning and I think Dean wins. I have no opinion on John.
Why would a hunter engage in a fair fight? Why would anyone engage in a fair fight? What does that even mean?
I always thought a fair fight meant the opponents were equally matched in strength and skill, not that they agreed to fight ... politely or whatever.
One of the guiding principles of krav is "fuck a fair fight" and over time, I came to not understand the concept anymore. There are unbalanced fights, like just about every one Sam will ever get in, but "fair"? It's not a concept that has a place with life or death.
I always thought a fair fight meant you couldn't pull a knife or a gun if bare knuckles had been agreed. Also you can't hit an opponent who isn't looking or has his back turned. I'm making these rules up but they seem "gentlemanly". ETA: Also, unless it is a fight to the death, no hitting the boobs or the crotch. I bet this is written up somewhere.
A hunter fighting for his life or even real life street fighting isn't going to follow rules.
"fuck a fair fight"
Would be the reality of fighting for your life.
"fair fight" was shorthand. They both realize they are going to fight at the same time, with little notice. They are facing each other, and neither has an advantage in position at the time they realize they are going to fight. Neither has an advantage in weapons. Etc. Etc. at tldr. A "fair fight" is unlikely to happen by accident, but an enemy might set one up.
I just made my reservations for F2F in Denver so everyone here should do that too. We can watch SPN dvds and squeal in person!