Hey guys, I had to repost this because I was having trouble  attaching the image to the original  post.

Thank You everyone for the awesome suggestions and help you have given me! I'll take all I can get! LOL. This one was really racking my brain. So, the logo went from being quite intricate to being very simplified, which I could not be happier about! This is a terrible picture of the logo taken on a computer screen. I'll be asking her for a new one for myself. She wants me to use the one in the bottom right-hand corner.

if that was my order I would suggest to put the baseball on each cupcake -- each one iced with the yellow icing and pipe on the red -- then just make one prominent flag out of the words -- but I wouldn't be opposed to making a hundred flags, one for each cupcake -- get those longer toothpicks -- print off the logo -- glue the flags on -- bam