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Yes

if someone files litigation, that's obviously gonna sour the relationship, even if "retaliation" is legal or not

Suing while continuing to work is an absolute baller move, but it has to be carefully coordinated. When done well, it puts the company in a terrible predicament, and they will be eager to settle in most cases.

And no, you definitely won’t have a future there.

It's probably even harder to prove that sort of retaliation than that he has been the victim of sexism.