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I'm applying for a clerkship with a judge I interned for this past summer. I assume the judge remembers me, but should I bring the internship up or just go with my generic cover letter? If I do bring the internship up, how do I do that tactfully without sounding too smarmy/ingratiating? The judge has hired former interns before, but I don't want to make it seem like I'm expecting anything or seeking favoritism.

I'd recommend mentioning the internship by way of noting either skills you furthered as a result of your time in the judge's chambers or what aspects of chambers makes you really want to clerk for the judge.