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I was wondering how long the average summer internship with Federal District Judges in NY is? I know its judge specific, but a general range would be great.

Also how long are summer programs at Big Law firms in NYC? In particular, Skadden?

Is it possible to do both within the same summer if the opportunity is there? Or do they both require too large of a time commitment to fit them into one summer?

It's very possible to do both. Most law school summers are ~12 weeks long. A very short stint at one job would be 4 weeks, a normal "split" length stint would be 6 weeks. The length of your program is often subject to individual negotiation, even if the firm has a default policy.

The best (possibly only) way to split is to accept a job and ask if you can split. Once they say yes (most will) you get the second job. Once you have both you negotiate dates with both.

Just bumping my post up to ask if anyone here has experience with Skadden over the summer, and how flexible they are about splitting summers?

This summer, the Skadden summer program is 10 weeks.