How do you break in a new baseball glove fast?

Just pound it in with a ball. If it's a brand new glove and you got pretty firm leather, the better the glove, the more stiff it's going to be and the longer it will take to break in — but the longer it will last, too. So just throw a ball into the pocket of the glove over and over again. You can also use a little bit of oil, but not a lot; don't overdo it. Other than that, just play catch, and the better you get, the more you want to play with somebody that can throw hard. If you're playing catch and going hard and you're catching the ball in the pocket, then it will start breaking in.