One guy walks out of the bank with 11000.00 and then another guy comes into the bank and cashes his check for 1000.00, same account but I just file on the one guy that walked out with 11000.00 correct? or do I file both on the CTR since it was the same account?

As long as the people conducting the transactions are also the beneficiaries, then just the first guy with the $11,000.

What if the supervisor comes in and cashes 10 checks on 10 different individuals for the same company, I just fill out the CTR on the person picking up the money, correct?

Yes

Whoa, Tex!

If the supervisor is cashing the checks on behalf of 10 of his/her staff, the ten individuals are the persons benefiting from the transaction, and you will need to create a Section A in your CTR filing for each of them, even if none of them would trigger a CTR is he/she had cashed his/her own check.

The supervisor gets listed in Section B unless she/he is also one of the Section A individuals.

But how do you know who is receiving benefit - perhaps those employees had been advanced funds from the supervisor, and the checks are now his. My point being that you only know what is in front of you and if the 'supervisor' is receiving the cash, then the benefit is his.

You bring up a good point and maybe I'm just playing devil's advocate. Thought I must admit, I always thought whoever you gave the cash to was who received the benefit.