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I worked until the end of last week, and did a fair amount of writing, but nothing that I could use as a writing sample (my fault, prolly, but I was doing small points and things like that.) There was a good case that I worked on a fair amount, and I could put together a writing sample between now and OCI. I have a certain amount of material on it, but it would take a good 15 hrs + to arrange and write it, and then another bunch to make it perfect. Should I do that, in order to have a "work product" writing sample, or should I just use my brief from 1L?

It's up to you, but I wouldn't kill myself over it. If your 1L brief is of good and high quality then I think that would be fine, that's what I used for my sample.

I'll assume you're a rising 2L. Use your brief. The chances that you'll put together something as cleanly written as you did in your LRW class are slim. Besides, no one even looks at these things for OCI. (Clerkships are another matter.)