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Trump's play here has been pretty transparent.

He urges his party not to vote by mail, knowing that means opposition ballots will be counted later and he will have a lead on election night.

Claims all the mail-in ballots going for biden is proof of tampering even though he specifically told his followers he wanted it that way...

I'll even say this: if I suspected I was going to lose an election like this, and I wanted to accuse the other side of cheating after, I might cheat myself, in such a way that I can prove it, then point at that cheating as evidence the election was rigged.

This is why he not only will have to prove there was cheating, but that the cheating benefited biden before he is doing anything other than whining like a stupid baby we don't care about anymore.

Saying "there are irregularities, therefore biden cheated" sounds like exactly what Trump tried to orchestrate his believe everything he says cult into believing starting months ago.

All fair points, the only problem is that the entire plan hinges upon him somehow managing to convince the courts that the election was illegitimate, and that was never likely to succeed.

Ironically, the stacking of conservatives on supreme Court actually hurts him here more than it helps because conservative judges care more about muh states rights mofugga than liberal ones do (in theory), and the Trump administration's beef with the election mostly lies on how certain states handled the counting of ballots. Even if his lawsuits managed to reach their way to the supreme Court (highly unlikely) The majority will side with the states.

So it's definitely possible that this whole debacle has been 5D chess on Trump's end, but at best it was going to always be a desperate hail Mary.