I am trying to figure out if I should ask for discovery extension in order to compel the documents or if I can still compel them after the discovery period is over?
I assume you are acting as your own lawyer. You are very likely in Federal Court given the question you have posed here. First, I recommend you seek the advice of a lawyer. The issue of what is or is not privileged is a reasonably complex area of law. Overall, many lawyer assert it very broadly when in fact you need to meet certain exacting standards for communication to be "privileged." For example, sometimes companies will assert the privilege as to any email where an attorney happened to be copied on the email. This in my view does not make a communication privileged. The over use of privilege by companies and some lawyers is a way to hide the truth. In some instances it is allowed. In many others where it is asserted there is no privilege.
You face an issue which is that the other side produced a privilege log and you did not immediately challenge it. Or at least I will assume that is the situation. If the discovery cut off has come and gone you have a bigger obstacle. I would say that given the fact you are pro se? the judge might not be has “hardnosed” as they might be with a lawyer.
In any event you need to call up the opposing lawyer and “confer” with him or her on the fact that you are going to file a Motion to Compel the production of some or all of the documents on the log. You will need to have reasons/legal grounds for your Motion. They will either agree to give up some or all the documents (unlikely) or say “no”..(more likely). Then you should go ahead and file your motion. Unless you have made the judge upset for other reasons I suspect they might allow it if it is well grounded. You could also target in on the documents you think are the best for your case and which you think you have the best chance to argue are NOT in fact privileged and ask the judge to review them, “in camera.” That just means without you seeing them. They can normally tell pretty quickly if the documents are or are not privileged.
Again, as you can see, this is not easy stuff. There are lots of ins/outs and judges overall dislike these issues as it forces them to make hard decisions.
Hope that helps a bit. Good luck.
This not meant to be legal advise. It is not possible to know everything about your issue in this forum. You should consult an attorney if you want a full answer to your question. I will not be taking any other action on your issue. I only work with clients when they have signed a client agreement with me and provided me with a retainer.
Generally the obligation to provide discovery is ongoing throughout litigation. If new requested documents come to light after the 'discovery period' is over, they still have to be produced. However, if documents are privileged then, by definition, you can't compel their discovery. Without knowing the context, it's hard to say much more than that. You really should consult with an attorney in private if you're going through a lawsuit.
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