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I think putting it under history is fine. The Pitch is an alternative newspaper that has been published weekly for 30 years, which would make it a reliable source (unless its known for publishing false stories, which it isn't). Story seems to have been picked up by a few other sites, mostly dealing with gay rights issues. LionMans Account (talk) 15:40, 14 May 2021 (UTC)[reply]
Publishing for a long time does not make a source reliable. See the list at WP:RSPSOURCES where many much older publications like the Daily Mail are deprecated. Besides being a tabloid type paper, it calls itself "progressive" on its about page, raising issues of bias. The Pitch would be useful for providing a viewpoint on a subject, but not original reporting. The same is even more true for the other sites you mentioned, especially since they directly rely on the reporting in The Pitch. --Jfhutson (talk) 16:06, 14 May 2021 (UTC)[reply]
There is a reason Daily Mail has gone through 3 RFCs over its credibility. Unless the Pitch has started publishing false stories (which I know of none), should be considered okay. Maybe its not a great source, but certainly more credible than Daily Mail is (or any source on the WP:RSPSOURCES bad list). The response from the school even suggests the reporting is factual. LionMans Account (talk) 16:26, 14 May 2021 (UTC)[reply]
I only mention the Daily Mail since your argument was primarily based on it being around a long time. The RS policy is that sources have "a reputation for fact-checking and accuracy." There isn't a presumption of innocence for old publications such that if it's not known for publishing false stories, it's reliable. I'm not sure why you say the response from the school suggests it is factual; the headmaster's letter directly contradicts the key contention of the story. --Jfhutson (talk) 18:05, 17 May 2021 (UTC)[reply]
Unless you have evidence this newspaper prints obviously false stores like Daily Mail and New York Post does, It should be considered an RS. It probably is not an RS for backing up WP:N, but being a high school, this school already meets that. LionMans Account (talk) 22:41, 18 May 2021 (UTC)[reply]
At the risk of repeating myself, that is not the policy. The policy at WP:SOURCE is that sources have "a reputation for fact-checking and accuracy." Having a reputation is a positive thing, not just a lack of evidence of publishing false stories. The fact that no mainstream sources (those with a reputation for fact-checking) have picked up the story would seem to indicate that this is not a reliable source. I'm also not sure why the reliability standard for establishing notability would be higher than for establishing facts. --Jfhutson (talk) 12:29, 19 May 2021 (UTC)[reply]