I've had one or another version of 375 Winchesters for 30+ years. Winchesters, Marlins, Savages. Killed my largest black bear with one. Done good on deer too.
But last year I drilled a black bear in the front shoulder with a 200 grain Sierra at 50 yards. Wife went with me and we called him out of his bed up to us. When he came in from the right I stopped him with a squeak and drilled him in the front shoulder. He took off like a scalded cat and gave me one more shot as he went out of sight. My wife looked at me and said, How could you miss that? LOL I said I didn't!
He left a blood trail down through and alder thicket and swamp for several hundred yards, and laid down twice. Tracking him in chest high salal brush and alder so thick we had to force our way through was hair raising, to say the least. He could have had us at any time. After several hours of tense tracking down the creek bottom alders, the blood quit. When it got so thick we couldn't see more than a 3 feet I called it. We went back the next day and no luck.
Fast forward to this fall. I had a friend that wanted to get a bear. He'd had a run of bad luck for a couple years and needed to punch a tag. I took him up in there and we got him a bear about a mile from where I'd called in the swamp bear. I told Liam man that looks alot like the swamp bear! When his wife was dressing it out she found a perfect big bullet hole in the left shoulder blade. The bullet was lodged just behind it and never made it deep enough to reach the vitals. She still has the shoulder blade but sadly the bullet got thrown out.
Tough ol' bear. had a bullet lodged in his shoulder for a year and still had an infected puss pocket around it and yet he was out doing what bears do.
I don't fault the cartridge too much, it works if the shot is rib cage or spine. But, as anyone that hunts knows, the shot isn't always ideal. My takeaway is work harder on exact shot placement with the 375 on bears, or go to the 358 and use Barnes 180 ttsx. The 358 runs several hundred feet per second faster and of course the Barnes holds together well.
I think the 375 is an ideal deer cartridge with the 200 grain bullet. I don't know if a 250 grain bullet would have improved last years results or not, I've not tried them. Here's Liams swamp bear. He killed it with a 7mm magnum.