To be honest, Ben's interactions with Jay mainly lay on the field. And it was on that grassy plain that Ben slowly revised the initial viewpoint he had had of him. From the moment he had seen Jay tumble out of the limousine, hopefully more playfully than brutally fighting Carlos for what he was still pretty much certain was a blanket, he had thought that he had had his character pinned down. He was a rough, fight first and ask questions after kind of guy with an abundance of strength and energy, coupled with a penchant for the occasional bout of flirting when a girl caught his fancy. Later, Ben would add an amusing addendum to that last bit, noting that Jay always seemed almost comically confused whenever he was rejected by a girl, yet was woefully confused when one showed any sort of real interest in him.
Past his initial greeting to them all and shaking his hand, Ben really did not speak nor interact with Jay in any real capacity until Fairy Godmother suggested (more like ordered) him and Carlos to participate in Turney. What was meant to be an energy burner instantly turned into a new spot opening on the team (and at Jay's insistence later on, a second spot for Carlos in an endearing show of loyalty) because wow, was he strong. Ben's torso ached just thinking about the brutal full on tackle he had received from Jay. He might as well have been an insubstantial flea for all he had managed to do to prevent it.
Nevertheless, having learnt his lesson from Evie, Ben knew better than to just limit his perception of Jay as being the brawn of the group. He was much more than that, and it was for that reason that Ben had successfully defended him against accusations that he was the one responsible for the ever growing list of things disappearing from the campus. It would be prejudicial of them to just accuse him based on who his father was, and, more than that, no one ever actually saw Jay in any of the locations where things were reported missing from. To his own ears though, his defence had sounded paper thin, but thankfully Fairy Godmother seemed to have seen the same thin as him because she agreed and promised not to look any further into the matter. And, if all of the missing items miraculously returned not too long after Maleficent's defeat (and Ben had not even noticed that two pairs of his gem encrusted wrist cuffs had been taken) and Jay's swearing to be good, well, that was simply pure coincidence.
With Jay as a teammate, Ben quickly saw a person desirous of companionship, acceptance and acknowledgement of his worth. It was obvious that he had led a very solitary life and was raised to rely solely on himself. It was probably why Jay had decimated all of them in that initial practice in the first place. It probably had never even occurred to Jay that he could pass, or allow others to protect him in the Kill Zone. Ben still chuckled when he recalled the way Carlos had screamed and cowered on the field. It may seem cowardly but Carlos had had the right idea and was the only one from the field that night not sore. When Jay was in that sort of one-mindedness mental frame, the best thing one could do for their own safety was stay the hell away.
Minutes before he had arrived to their first official practice as a new unit, there had been a murmur of worry among the other boys, but it proved unnecessary. It seemed that Jay had had a good conversation with the coach, and gradually, made more concerted efforts to just function as a part of the team, though there were admittedly many hiccups along the way. Ben could never forget the shock on Jay's face when he had actually assisted another player and was thanked by him and commended by coach who pointed out that see Jay, you saved yourself a lot of energy and take the opponents eyes off you as a target by simply just allowing the team to assist you.
Jay had just rubbed his helmet ruefully in response and said, mostly to himself, "Yeah, I'm starting to see how working with people aint such a bad thing". There was a story behind those words that Ben eventually hoped to learn.
Ben's second proudest moment with regards to the strong teen was the way he had actually worked in tandem with him and Carlos to secure victory for them. The pure pleasure and happiness and realisation that showed on Jay's face was priceless to him, which was why, even in the midst of Mal's spell, he had led the effort to haul Jay onto their shoulders and allowed him to have the trophy. It was much more than a victory for them; it was a moment of personal triumph for Jay that, from that moment on, reduced the tension he carried in his shoulders considerably and left him entirely more approachable to the general student body. Jay developing his own personal fan club among the girls was just an added bonus Ben was amused and surprised to see that Jay did not take advantage of. But then again, he reminded himself; Jay seemed forever flummoxed when a girl made a move on him.
His proudest moment Jay though, was of course the moment he declared in front of the entire Hall that he had chosen the path of good. And Ben was glad of that. He had seen the pained reluctance in his eyes while Mal had struggled between stealing and returning the wand. He could have sworn that Jay's barked laugh when a random teammate called out his name was laced with choked back tears, and he was oh so happy and proud when Jay made his declaration, effectively ridding himself of the last remnants of the isle's hold on him.
Jay was indeed the perfect model to show how sports could turn around a person's life. Yes it was not the sole factor, and it was such a large contributing factor to it. Ben was just glad that he had been given the privilege of seeing Jay blossom into the person he was now, and could not wait to see just how much farther he had to go.