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I received an offer from both firms and am debating between the two of them. Wondering what everyone thought. I think I'd prefer to be in New York and to establish a career there but am just wondering if there's a significant difference between the prestige of Skadden and that of Simpson?

I'd like to get into NY politics, ultimately, and although that might make Simpson the obvious choice, Skadden DC does have a super Washington insidery feel to it. Might not be too bad to network with that crowd and then get back up to NY somehow. Simpson's Private Equity practice, however, is tops so that's probably access to some important people to know in NYC.

All D.C. firms have an "Washington insidery feel" to them. Probably because they're, you know, inside of Washington D.C.
If you want to work in New York, go work in New York. If you're that concerned about Vault rankings, maybe find out how common it is for Skadden associates to switch offices.