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You seem very confident that he will read a 70-page manifesto about why his parenting decisions are wrong and bad.
You say that you know him well enough to believe this is a reasonable expectation, but from what you've written about him and his wife, this seems unlikely to me. They appear to have embraced the view that gender is something distinct from sex that children can choose, and that denying their son his choice will damage his mental health and possibly cause him to commit suicide. Assuming he respects you enough to take your concerns seriously, I would suggest that you try prying at cracks in his worldview with some judicious Socratic dialog. Just dumping a bunch of horror stories about how he's going to maim and damage his son, however earnest and heartfelt your intentions, is probably not going to make him read all the way through until he slaps his forehead and says "You're so right, what I fool I've been!" I mean, how many people do you know who are actually persuaded at one fell swoop to alter their worldview?
I don't. I expect it to make him deeply uncomfortable and hopefully start the process of convincing himself that he needs to change his approach.
The problem is you need to have certain facts in common. If he says, "We need to affirm his gender identity otherwise it will lead to higher risk suicide." I need to be able to say, "Did you read the analysis I sent you? Did you read the actual details of the studies that were making these claims? I can walk you through it line by line if you want. Your best bet of avoiding suicide is by getting Skylar off this train." Without actually giving him an opportunity to mull it over at leisure in written form, there is no way we can agree on a common set of facts. And if at worst, he doesn't want to look at it, at least I am arguing from the moral high ground of actually putting in the work to find the truth.
Cordially, please get your head out of your buttocks and do what's best for your nephew/cousin-twice-removed/whatever. This approach is folly. You've received a unanimous chorus of feedback telling you it's folly. Do you want to save your kid relative or does that come after making the father agree with you on gender ontology?
Right now, the parents have socially transitioned the kid. The path of least resistance will be toward following the WPATH "best practices" with the the tragic result of medical transition at at age 12, unless he steps up and questions the therapists and the experts and the gets the train turned around. The dad has to become uncomfortable at some point if he is to pull the emergency brakes on this train.
Seems to me my options are:
Send a much shorter email with a few key links. Problem with this is that it only gives him a fraction of the information he needs to know, and so unlikely to make much impact in reprogramming him and budging him from his path.
Drip out a lot of content over a long period of time. Problem with this is that it draws out the conflict, and will him and maybe his wife dread seeing me
Drop a big info dump on him, tell him I'm not going to draw out the conflict, but I do hope he seriously considers everything I wrote. He will at least be exposed to the information he needs -- and hopefully that will provide the foundation to at some point step up and make the changes he needs to make.
I will admit, in my writing I do have a messy mix of emotions -- genuine concern for his son, but I also have genuine anger at him for being so effing stupid about this issue and then one time correcting my own daughter about what is a boy and what is a girl (and not just stupid -- I think I detect some amount of self-righteous pride in being more "progressive" on this matter). I'm not sure I want to completely hide this anger, as I think it is coming from the right place.
Oh lord.
I'm sorry, dude, but this approach is steeped in ego and your need to be right.
You talk of "reprogramming" him, as if he has no agency and you are a scientist trying to reverse the zombie plague that has infected his brain. Maybe this is actually how you see it, but either you're wrong, in which case you're being arrogant and patronizing and he will see through it, or you're right, in which case you are not offering a "cure," you're just staging a futile gesture that will make you feel better.
You are not focusing on the most efficacious way to persuade your friend and help your friend's child while still staying in their lives. You are focused on winning. Hell, you even want to unload on him about past petty grievances ("He said something stupid to my daughter and I need him to understand he was wrong!") and you have convinced yourself that this is the right approach because you're right, dammit.
Your friend is not on the Motte. You are not arguing with us randos on the Motte, who can dispassionately (or heatedly) parse walls of text like this and get into the weeds and analyze abstract arguments.
You are understandably emotional about this - and that's not a bad thing, I believe your heart is in the right place! - but your approach seems doomed to failure to me, and that there appears to be a near-unanimous consensus agreeing with me should give you pause. You know, if you actually think considering arguments rationally and evaluating evidence is important.
Verbally grabbing your friend by the shoulders and shaking him for 70 pages saying "Listen to me, you fool!" is not going to work. You say "He will have the evidence available to him." Sure, assuming he doesn't delete your email. You actually think because you're so "high status" that he's going to read through every word and click all those links, while you're going on about what a self-righteous wrong-headed prick he is?
Ultimately, you don't actually have any say in what he does with his son. So you're right that being That Guy who brings up how he's parenting wrong every time you see him will probably lead to him and his wife not wanting to see you. Maybe this manifesto-dump will put some cracks in his worldview. But I would strongly recommend you take a softer and slower approach, minus the "I need to reprogram him" attitude. Express to him, kindly and politely, your misgivings and some reasons why you think he's making a mistake. Tell him you understand he wants to do what's right for his son, but you hope he'll consider what you're saying. Tell him you'd be happy to talk to him in more detail about it over coffee, any time. Forget about "that one time" with your daughter that's still chapping your hide!
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The way I see it, the most reasonable goal for you here is simply to prevent the medical transition of his son. If you can fight a successful holding action until puberty hits, testosterone will likely do the rest of your work for you. What pronouns the kid uses are irrelevant. What the father thinks about gender identity is irrelevant. Let him be called genderfluid, nonbinary, queer, or whatever else as long as he doesn't get on puberty blockers. Agree with the father that if we had Star Trek perfect sex-change surgeries then it would be great to try out being a woman, but our medical technology isn't that good, and the interventions we have now will do permanent damage to his child. In 20 years nearly every man of that generation is going to have a story about some weird gender stuff that happened when they were in grade school and no one will care, as long as they didn't sterilize themselves.
This is not about you and your anger at him or at the wider societal changes going on. This is about the life of a single child. I have seen families torn apart and destroyed by matters of far less weight than this, so I can only implore you to choose your words carefully and to make it brief and to the point.
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