Last weekend during the Mets-Astros broadcast, Keith Hernandez talked about breaking in a baseball glove. He used two mitts per season in his playing days which came as a surprise to me. I thought a player would hang onto a favorite glove for longer than that, but Mex talked about liking his glove to remain stiff, and I suppose that makes sense for a first baseman.
As a kid I loved the ritual of buying a new glove and breaking it in.
On that note, check out this cool article on craft of glove repair over at A Continuous Lean.