Assuming there are no promises involved, the second email doesn't assure anything other than he likely lost a few more WE points after sending it. A lot of us have tried to intentionally get players to quit our teams by not playing them (so as to not take the reputation hit by outright cutting the kid) and finding that we were still stuck with the dead weight the following season anyhow. I know at least one time I got three complaint emails from the kid and he'd bled off 20+ points of WE, but he was still back on the roster for me the following year as a senior.
If you can get his minutes up, you can recover most/all of the WE loss. My understanding from support exchanges years ago was that if there is any WE loss, there's a chance the kid chooses to leave the program at season's end. But it is by no means a sure thing that it happens.