A 500S&W is a huge step above the 50AE. The 500 can generate up over 3000 foot pounds of energy and is capable of 700 grain bullets. It ought to flatten a brown bear with extreme prejudice. I'm thinking end to end penetration at almost any angle with the right bullet. A 44mag will still certainly kill any bear but will require a bit more precision. I have severed 6" hardwood trees with a single shot with a 500. My 44 would require 5-6 shots to acheive the same.

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NRA Instructor / Life Member