Try and get him logon, have it fail, and get the logs from client. In the %programdata%\vmware\vdm\logs folder I think there is a debug log. Search for his name and there should be an error that might help narrow it down. I'm pretty sure that log should show him starting to logon but something interupts it. I'd look at using AD groups for entitlements too, I'm using ad groups for global and local entitlements. That way if I need to swap someone out its pretty straight forward.
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