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I am wondering if there is a point in one's career when it's too late to clerk, in terms of either the difficulty of obtaining a clerkship or the clerkship's effect on one's career. I imagine that some judges wouldn't want to hire a clerk who is something like ten years out of law school because all those years of practice could bias the clerk's perspective. Also, I imagine clerking ten years out of law school could raise some eyebrows among potential post-clerkship employers. I've heard of law firm associates leaving their firms three years out of law school, but there must be some point at which it's really too late.

If the above is correct, when is that point when it's too late?

Also, would the point depend on the clerkship? For example, would it be more acceptable to post-clerkship employers to take a more prestigious clerkship (e.g., 2d/9th/DC Cir.) late in the game?

I'll bite.

I clerked for the second time approximately six years after graduating. Now, I'm a public-service guy and was looking for pivot, so it made sense; I didn't have to worry about being too expensive or having to answer uncomfortable questions from firms. But I was the oldest clerk by far, and there was the intangible feeling that I was at the far end of viability.

some judges value experience more than others, so it's no problem if you've been out of law school for awhile as long as you target judges who want experience, and explain why you want to clerk in your cover letter. It is at the very least unusual for someone with 5+ years experience to want to clerk, and if you don't explain it, the people reviewing your application might assume the worst (fired, burned out, flakey).

It really depends on how you talk about it. For example, if you work in private sector for 5+ years, and suddenly you want to pursue a political career instead. One or two years' clerkship could be a nice career transition. As long as you have a legitimate reason, work experience will be favorably looked.

The only scenario I can think of being too old to clerk is when you are older than the majority of the judges/justices in the US. I don't think they are comfortable hiring someone older to work for them.

From what I've seen within 5 years of when you graduated.

From what I have observed (correct me if I'm wrong), but I would also point out that while federal clerks tend to be younger, SSC clerks and state judge clerks in general vary widely in age. Many SSC clerks I have known were 5-10+ years out of school.