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If I spoke to someone familiar with the judge who does not know my work product, should i still name drop? For instance, should I mention in a cover letter that a former colleague of the judge recommended that I submit an application even though that colleague has never worked with me? I can see them signally genuine interest but also, making me look like a dope if that person is called who then says "no idea about him."

Name-dropping is usually a good idea so long as it's done tactfully because it makes you stand out among a pile of applications. Just make sure the person whose name you're dropping is aware. (Maybe send an email that says, "thanks again for meeting with me. You recommended I apply to Judge [x]. May I mention your name in my cover letter?").