HS Anon

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One of HS Anon's pictures of Greg, can be found here and note the "onision.com" at the bottom.
HS Anon, short for High School Anonymous, was a lolcow poster going by the name Michael who claimed to have gone to high school with Greg. In 2015, AS Anon answered question from board members and was interviewed by SomeGuy827.

Evidence

Most, if not all of the accurate information from HS Anon's account of Greg's time in high school can be traced back to the 2005 and 2006 Wayback Machine archives of Greg's Onision website. Some people take this as proof HS Anon was legitimate, while others use this as proof Anon was a troll and researched the archives before posting.

HS Anon provided pictures of Greg and his family members, claiming he and his friends saved the images during High School from Greg's Myspace and from their school's online bulletin board. Suspiciously, all of the images HS Anon provided are all archived on the 2006 version of the Onision site. Some of the images posted by Anon say "onision.com" in the corner of the photos. Greg did not begin going by "Onision" online until 2005, a year after graduating high school. (Source) Another piece of evidence against HS Anon is that in his stories, he mistook Alicia (Greg's ex-sister-in-law) for one of Greg's biological sisters. On the archives of Greg's Onision.com photo gallery, Greg referred to Alicia as his sister. (Source)

SomeGuy827 claims that before he interviewed Anon, he was shown proof that HS Anon went to the same high school as Greg.

Image Board

On August 29, 2015, "HS Anon" came to an image board thread dedicated to following Onision and his drama. He posted a long, eight paragraph tell all about his supposed years of knowledge on Greg based on their time in high school together and from mutual friends. He began answering questions from other board members and began posting old photos of Greg. He claimed he had these photographs because he and his friends would save images of Greg from his MySpace as a joke. He answered questions for hours until he said he would be back to answer more questions the next day. He did not return and instead contacted Someguy827 for an interview.

Interview

On August 30, 2015, SomeGuy827 uploaded his interview with HS Anon to Sound Cloud. (Source) He distorted Anon's voice at his request to hide his identity. For over 40 minutes, HS Anon answered Some Guy's questions, told stories he supposedly witnessed or heard of through friends, and gave his opinions about Greg.

Reaction

Greg reacts to HS Anon
On November 2, 2018, Greg uploaded an hour and a half long video reacting to HS Anon's interview. Within the first two minutes of the video, Greg begins debunking HS Anon's story. A few of the points Greg made against HS Anon were that HS Anon calls him “Gregory Jackson”, when Greg went by "Gregory Daniel" in High School. Another point was that HS Anon claimed he went to school with Greg all four years of high school, but Greg did not go to the same school all four years. Greg also says he was not a vegetarian in high school as HS Anon claimed. He was a vegetarian as a child, but did not become vegetarian again until he was 23. ($ource)

After her return to the internet in 2019, Skye was asked about HS Anon. Skye said, "Some details are strikingly accurate, while others about me were speculative. Seems like a friend of an old friend. Like for example, I have never had children, thus there is no secret love child (lol). Probs just did hardcore readings of his old blogs through WayBackMachine." (Source)