Constant losing is a product of not developing your players and building a program through developing your players. I never won a JV championship. I was too busy trying to develop all my players so they could help us win a Varsity championship and move on to play in college. I didn't allow them to ride one or two arms. I didn't allow the to set a line up. That JV SS might need to play CF the next year behind my stud SS because my CF was graduating. So he didn't star at SS on the JV. The focus is on getting better as players. Learning what working at getting better really is. Learning that its not about the games it's what it takes to be ready for the games. What you do when no one is watching will determine what you can do when everyone is watching.
Most kids entering HS have no idea what 3 hours a day 5 to 6 days a week on a baseball field is about. What the weight room is really about. What physical and mental toughness really are. They have to be taught how to win, win each Day, Hour, Minute they are at the feild. The games are cake. They are the reward for the hard work and dedication that it takes to put on the jersey. I coach my butt off so I don't have to coach on game day. If you have to coach on game day you already lost the game.
Why did my JV teams that were lucky to go .500 win multiple Varsity Championships against the same kids 1 2 3 years down the road? Why do some programs always seem to win no matter who graduates? Why do some only have success when a good crop comes through and then they always seem to underachieve?
Winning is an attitude that is developed by knowing you have done what it takes to win. You go to sleep knowing no one else could have worked harder than you. You have confidence because you know you have put in the work. JV should be about development and learning what it's going to take for you to have success both as a player and a team mate. When players understand this you don't have to do much coaching. You teach. You mentor. You encourage. And if anything you have to hold them back at times becaues they catch fire and won't stop. The younger players catch this fire and it's on.
I never had a team go into a game hoping to win. They expected to win. That comes from knowing you have earned it before the game is played. That is a winning attitude and it is developed by the way you things each and every day.