"Transphobia (or much less commonly transprejudice) is a range of antagonistic attitudes and feelings against transsexuality and transsexual or transgender people, based on the expression of their internal gender identity (see Phobia – Terms for prejudice)." That is what Transphobia means, it does not mean he's afraid of someone. The word phobia does not automatically denote fear of something. In this case, this "joke" as you keep so nicely referring to it is antagonistic toward Caitlyn Jenner because even though he uses her proper pronoun's, he is still implying that if she were to let herself go, she might look similar to his clearly male friend there. Implying that a woman who has transitioned would look male if they "let themselves go" is inherently transphobic. Freedom of Speech is there so there are not legal consequences to what you say, however there can and will ALWAYS be social consequences to what you say.