Dude committed several genocides because he had mommy issues and killed the first woman he had sex with because she sided with his adoptive dad on whether being strong or being reasonable was more important and then decided to join the literal fascists. It doesn't get any more masculinity troubles than that.
Jedi took Anakin as a small boy away from his mother and told him "not to worry" about her (a slave on a hostile planet), because apparently experiencing fear is a slippery slope towards becoming an evil mass murderer (warrior of the Dark Side).
Then, when she was killed, he was not allowed to grieve, either.
Then Anakin got visions of Padmé, his wife, dying in childbirth, all while Jedi restricted any marriages to begin with and essentially have cut him out of any counseling, while Yoda doubled down on "ignore your feelings" line.
The entire story of Anakin on the Light Side is the story of everyone neglecting the absolute base emotions he has experienced and trying to raise him as a "tough man" he never was.
Palpatine has seen all of it unfolding, and he knew very well Anakin wasn't an emotionless robot Jedi wanted to make of him, and all it took was exploiting Anakin's raising wave of anxiety over Padmé's fate along with his desperate escape into careerism to switch him to the Dark Side, where he, as Darth Vader, will end up destroying worlds and commanding an authoritarian dystopia.