He chose Malcolm and Bright at the same time and only had to change his name once.
Once he transitioned, it was much, much easier to avoid being recognised as Martin's child. He got 2x as much garbage from his classmates until Jessica put him in another school.
Jessica believed (read: hoped) that the transfer would solve both problems, but unfortunately all rich people schools all have the same tendency to gossip so while he doesn't get bullied for being trans again, he is quickly revealed to be Martin Whitly's son.
Malcolm knew that shouldn't make him happy, but he'd been Martin's "golden girl" for years, and being his prodigal son instead brought the most repulsive sense of relief he ever felt.
He met Vijay at the second school, and told him he was trans. When Malcolm and Vijay have their friendship breakup, Malcolm is so angry and hurt that everyone is scared for a minute that Vijay outed him or was transphobic, but he wasn't and their relationship is the same as the show still. (Martin never gets quite clear on why they fought, and was careful when talking about it, which is hard to do when you're trying to manipulate your teenage son into being a complete loner.)
Jessica was frustrated when Malcolm never wanted to wear the fancy dresses she bought him as a child, and once he came out, she tried again with extravagant and over the top suits, which also did not work. Malcolm wore suits and dress clothes, but he refused the brightly colored patterns his mother brought. Jessica tried to teach him that it wasn't girly it was stylish. Malcolm knew he just didn't like the suits, so she just took every chance she got to dress Malcolm up (i.e. white suit).
Malcolm knew who he was from a fairly young age, so Ainsley doesn't even realise he's trans until shes older and someone makes a comment at a dinner party, asking about Jessica's other daughter and Ainsley short circuts trying to figure out who they mean.
She eventually goes to Malcolm to see if he knows something and he says he has no clue, but that Jessica did have a few boyfriends other than Martin in her life just to throw her off the scent.
That's the moment that starts the sibling rivalry over who the better investigator is because it took Ainsley a week to figure it out.
Gil and Jackie were always the most supportive. He came out to Gil first, and he helped him come out to Jessica and figure out his transition. They did all the typical father-son things: baseball games, stakeouts, playing cath in the yard. Gil tries to give Malcolm all the male bonding experiences he otherwise wouldn't have been able to get.
Speaking of... Martin takes it more than well. He wanted a son, and thought he wouldn't get one, until Malcolm came out, and Martin sees this as him being even more like himself than he thought possible.
Martin [in his "woke serial killer (as a killer? No as a man.) way] is pretty forward thinking for the 90's. He gives Malcolm trans role models and does a lot of research on the subject to make sure Malcolm always sees him as his savior and idol. Martin does the whole "it's a cruel world that hates you specifically for who you are, and I am your safehaven" speech, but actually intends to manipulate him instead of just accidently making him feel bad.
John is a transphobe, but he's scared of Martin enough to know never to take it out on Malcolm or talk bad about him. If Martin hadn't been caught, they probably would've fought more over how Martin raises his kids, but Martin kept him in line until he was arrested. He gives Ainsley the angel as a show of favouritism.
Malcolm had enough resources to make sure most people in the fbi don't know he's trans, but he can't hide being Martin's son and when it rains, it pours. He gets outed the same day he's fired. The events are unrelated, but do ruin his day completely.
I don't think he tells anyone on the team in season one. He might spill to Dani when he got high, but she's kind enough to keep quiet until he's ready (and sober) to tell her again if he did.
They'd all be accepting, but it's just something he keeps close to his chest. He's not ashamed or afraid, he just likes his privacy and has had more than enough trouble for other aspects of who he is. He can be out as a serial killers son or a trans man, both is too stressful.
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