I have absolutely zero recollection of this event, what the heck
Also those old fence and sign graphics... amazing
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No idea here, either. It seems to be right after I won that hat in an event, at least judging by the screenshots around it. Looks like Andy is in there as well.
There were a few other screenshots like that. I found a screenshot of a CTF leader board with Mashboyellis on it - at the time I had no idea who he was, but I hired him as a GP over a year ago.