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So here is the situation: An awesome MidLaw firm that I'd love to work at is coming to my school's spring OCI. I know someone who is closely related with a partner at that firm and used to work in the recruiting department for a while. Should I apply to OCI and give that person a heads up? Or should I try to bypass OCI and try to get the job through this person?

You should probably call that person and ask them what they think.