It's never enjoyable. It's never easy. But it's one of the realities of playing travel sports. In youth travel baseball, there is a balance between giving opportunities to as many kids as possible and making sure the individual kids get enough repetitions. What this means, then, is when more kids tryout than there are spots available, teams cannot take everyone. This leads to what we have found is the most difficult aspect of youth sports: roster cuts.
The first time I had to call a parent to let them know their child was not going to be a part of the team was exceptionally difficult. This child had played with our team for several seasons. I had built relationships with the player, his parents, and his family. The player was 9 years old and was about to be cut for the first time in his life. It felt like an enormous weight on me as a coach, and yet after that phone call my life would move right along, our team would continue to function, and that child and his family would be left with the disappointment of no longer being part of a team they wanted to be on.
I won't spend time pontificating about the good and bad of travel baseball. As you might presume, I feel the benefits of youth travel baseball far outweigh the negatives which is why I and my son participate in travel baseball as opposed to alternatives. But one aspect I find quite difficult to manage is that of competition vs. development. On the one hand, it would be quite simple to take a group of friends, have them play baseball together and grow for years, only adding new players when current team members left on their own accord. The downside, however, is that just as their might a group of players best served by this model, the top players might miss out on seeing some of the very best competition. Furthermore, whether parents want to admit it or not, winning enhances the experience for everyone involved. No child or parent (or coach) wants to be part of a team that loses all of their games, no matter how much development their individual child achieves. Consequently, there is always some pressure on coaches to provide opportunities for all the kids on the team while also achieving some success on the field.
Our own team holds 1-2 open tryouts per year (Summer and Winter). While we go into these tryouts with some idea of the team we want to come out of the tryout with, we definitely approach these tryouts as open to anyone who is interested. We feel we owe it to our organization, our current team members, and anyone interested in trying out for our team to provide a fair shot at making our final roster. We make roster decisions based on a variety of factors including talent, roster size, position needs, and opportunities available for each individual kid. We can't take the starting shortstop from every team around because there's only one shortstop on the field at a time on our team. We usually have approximately twice as many players trying out for our team as we have spots for. I've had to cut the sons of friends, colleagues, people who have been with the team for some time, or even families who just joined our team the season before. Through that, I've learned a bit about navigating these discussions and also where I (or we) as coaches might be lacking in our assessments and decisions.