I was putting together a new load for my .300 win mag last night. I have always had a real hard time pressing the cases back into shape. I almost broke my reloading bench doing it! I really have to lube the crap out of the case in order for it to be easier. Has anyone else had this problem with Winchester brass?

Never....how many times has your brass been fired?
What kind of lube?

Something is not right on your setup, one of your components, or your technique. Yep, I should have been a genius

No brass should be giving you this trouble.

Do you load other calibers w/out this issue?

In my experience lube issues are generally ... too little and the case goes into the die well but doesn't always come out. Too much and you get some dimples on he case shoulders.

Have you tried annealing the brass?

sounds to me that you are loading your cases HOT and that the chamber in your rifle is a little on the generous side...

at least that is what the problems are related to when that happens to me.... in any caliber

What do you mean pressing them back into shape?? You should only be "minimally" resizing your cases to fit your chamber. Sounds like you should think about re-setting up your sizer die for a minimal shoulder set back (.003" or so). What type of lube are you using??? It may also be hanging up on your expander. What type and brand of dies are you using???

I had a similar problem on the retraction stroke resizing 243 brass. I will not buy another hornady resizing rifle die. Their expander sucks. I may buy a different expander or new resizing die. Love their seater die though. I use the wax lube.

Yep, My pop has been dealing with this with brand new bagged 284 Win. brass from Winchester. Once fired factory loaded cases from older store bought ammo size up just fine, not the new brass. The new brass is too hard and too thick, especially in the neck. He's not going to anneal and neck turn new brass. It's on its way back to Winchester.

Methinks it's a case of operator error.

Make sure the dies are clean and not scarred. Disassemble, degrease, lube with a bit of whatever case lube you're using. Go back to the sizing die instructions and follow them to the letter for full length sizing, then set your die a half turn or so higher and size one. If the problem is on the upstroke when you resize the neck make sure you're lubing the inside. You can also chuck up a caliber size bronze bore brush in an electric drill and clean the inside of the necks before lubing and sizing. You may be surprised at the amount of crap you knock out. If that doesn't do it I'd be suspicious of the die specs.

I only use Win. brass & never have a problem like this. I agree with the above comments on your sizing die not being set up correctly. Barring that, hot loads & a "generous" chamber. Go back thru the insrtuctions on setting up the sizer first.
Bear in Fairbanks

Are they small base dies ? They can make resizing hard even with plenty of case lube.