I don't know if I could be proud of a team I was a coach for (mostly the same administrative assistant role for me), even if they made the Little League World Series, if those kids, parents, and coaches were a bunch of a-holes.
On the other hand, several years ago, when I was coaching an indoor 10u flag football team, we were the worst team in the league by a long shot. Those boys were a bit upset after the first couple of games. It messed with their heads when I was proud of how they played together, shared the ball and responsibilities, and didn't get down on each other. I told them not to worry about the other noise, have fun, and learn something as that is why they signed up. I would try to get everyone touches in every game, and toward the end of the season boys would give up their touches for a chance to score or just to give a different boy a carry. I threw in some trick plays for them as well (had to have fun right?). Finally, in the last game as time was winding down, they begged to run the fumblerooskie. I had cleared it with the ref for a game or two but hadn't pulled it out. Not only was it a trick play, it was a trick play to the slowest kid who had the biggest heart on the team. The boys ran it to perfection and he rumbled 15 yards for the only touchdown of the season. You'd have thought they won the Super Bowl the way the celebrated.
I have a few such stories coaching youth sports over the last 15 years or so. Bad parents/coaches/teams do come up in those stories, but thankfully most of them are the good sort of stories.
I've been lucky to have many mentors in coaching kids, starting with my own father and several of the other coaches I've worked with over the years. I can sum up most of their philosophy into one word Respect.
Respect the game by practicing hard, playing hard, and knowing the rules
Respect each other by giving your best effort on your assignments and building up your team mates not tearing them down.
Respect your coaches by listening when they are talking, learning how the drills work, and showing up on time with all of your equipment
Respect your opponent by competing to the best of your ability, refraining from and ignoring trash talk, and by being gracious in victory and complimentary in defeat (even if you don't feel like it)
Respect the officials. You can't have a game without them. If you have a problem with one of them or don't understand a ruling, come to me and I will talk to the official.
I know I'm not the best X's and O's coach, I'm only ok in coming up with fun drills to learn fundamentals, and I'm shaky at best with in-game scenarios (but better a clock management than Davie), but I feel I do a good job of getting the kids to have some fun and grow, which is what it is all about after all.