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Yes I did have some 20 yr olds in the NHL.
But it happened again starting my 4th season. It appears that if there are more than 3 20 / turning 20 yr olds on the protected list, you can't sign any that are free agents or bring up any that were sent down to the minors (by accident...). (At least that's how I remember it, I'll try to keep notes next time.)
I had 4 OAs on the protected list (2 in the WHL, 1 in the minors, 1 unsigned). Once I traded one of the signed OAs and had only 3, I was able to move 1 from minors and sign the other.
One other thing: the only way to trade, using "shop a player", an OA who isn't signed is to sign to a contract and then trade. If I already have 3 signed OAs signed, I can't shop any of the others without trading / buying out one of the already signed ones.
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