A while back I purchased a new Rawlings glove. Paid good money for it, too. Anyway, I can’t get it broke in/softened up. It just takes too much effort to squeeze it shut. Tried everything, most recently I used a good Nakoma product, inside and out, covered it with a towel and let it sit under the front wheel of my truck for several hours. Helped some, but it’s not what it should be. I had been playing 2-3 games a week with it, but finally had to go back to my old glove.
I use this stuff I found at a local sporting goods store. It’s a leather conditioner that came with a nylon harness. You lather up the glove, place a ball in the pocket, use the harness to close the glove around the ball, and then place in a 200 degree oven for 30 minutes. I’ll let the glove rest for a day then repeat the process again. I do this with a new glove, and then after the season is over. Works like a charm.
That stuff will soften up the leather. I recommend it. However, it does not really “break-in” the glove. What I do is leave the glove around in places where I have down time. Then, whenever I have the chance, I will grab the glove in both hands and quickly flex it so the pocket area is rolling back and forth from my hand movements. Do that for a minute and set it down. Next time you see it, do it again. And on and on. It will break in quicker than just letting it sit until next used.
I always used linseed oil all over the glove, put a ball in it and tie it shut (thumb to ring finger). Then, just play a lot of catch with it.
I used to play with a guy who also used linseed oil and tied it shut, but then he’d bake in the oven at low heat, about 300 degrees, for a short time, probably 5-8 minutes. He did that with every glove he owned, swore by that method. I never tried it, but it’s something to consider if you’re having a hard time breaking it in.