I just had a thought while watching this again.
It’s an easy guess to think that City College is involved, there’s also another theory that Pierce is doing this. Here’s my thought: Pierce is sponsoring the paintball game so Annie will win. He hires the ringer to ensure that she gets the prize. She needs the money for a place to live and to pay for school and they bonded earlier.
The only thing about this is that the TV Handsome stranger and Annie had that little showdown in the classroom. It’s possible that he did it to draw out her friends to eliminate them.
Or I could be way off. Either way.