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This sounds crazy but it is the best way!Take two balls (plastic if you have them).Put them in the pocket and palm where you catch the ball.Wrap it tight with a bungee of string,Fill a 5 gallon bucket with hit water and submerge the glove in the water(you may have to put something on it to sink it).Leave it over night.Take it out and put it where it can dry.It may take a couple of days.Take the bungee off start playing catch.It will break in the stiffest mitt,I promise.
You'll also have to buy another one in six months after it falls apart.

Just use it, take it to a batting cage when it's not very busy, drop a few quarters in the machine and catch about 5-6 rounds. It will break in naturally.

Leather has natural oils much like your own skin, which protect the leather. When dunked in water and let dry, those oils are washed away. Without those oils the leather dries out and cracks.

Ever notice the inside of the glove where your hand goes, (if using without batting glove)after a while it gets brittle and cracks? It's becuase of the perspiration from your hand, it has the same effect.
You can't break the glove in overnight and you don't want to make the glove "floppy" or to try to make the pocket deeper/bigger. The best advice is from Gloveman to just "use it". The added benefit of this technique is that he'll have to use two hands to catch the ball. Make sure the glove is oiled/cleaned/tightened regularly and isn't used to clean off the plate.

Some gloves have thicker and better leather then others and will require more time. My son usually buys a new pudge glove every two years with the expectation that he won't use it very often as a game glove for 6 months to a year.
This may not be the best way but this is the way I did it.
Catcher’s mitts are the most difficult to break in and have a relative short life after they are broken in. I would always have two catcher’s mitts for my son. He would have a “game” mitt and a “practice and warm-up mitt”. By the time the game mitt was seeing its' last days, he would convert the “practice” mitt to a game mitt and pass the game mitt on to a younger player. I would purchase a new practice mitt and start the cycle all over again. My son continues this practice in college because he gets a new catcher’s mitt each year and uses last year’s mitt until the new one it is broken in.
Years ago I used to try to accelerate the break in period with water, heating the glove in the oven, pounding it with a bat, storing it under the mattress, neatsfoot oil, shaving cream, etc. etc. . . . but to me the best method for glove break-in properly maintain the leather and good old use. During the break-in period I would condition the leather with glove conditioner, store the mitt with 2 baseballs in the pocket, and wrap it tightly with saran wrap. After break-in the gloves and mitts are ALWAYS stored with a ball in the pocket to maintain the proper shape.
Hope this helps,
Fungo
Based upon my son's experience with his pudge glove (5 years and still going) the most important thing you can do is respect the glove by making sure it is clean and oiled (vasoline will work) as if it were new all of the time.

A good catchers glove used properly and keep clean will last a Babe Ruth thru high school level player 4-6 years. If the catcher cleans the plate off with the glove, never cleans it, never tightens the strings and catches the ball in the web or somewhere other then the middle of the pocket, the glove will be an undesirable mess in a year or two.

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