The resident DeSantis obsessive (onetruephilosoraptor) made me think about this with his latest Trump-critical post. On one hand, Jeb Bush has been seen at DeSantis events. On the other hand, Caitlyn Jenner has been seen hanging out with Trump's kids/niece. Neither have officially endorsed any candidate but their feelings are clear.
On one hand you have a dude who, through his very public existence, helps in some way to normalize trannies. On the other hand you have a GOP, Inc dweeb who wants to bring America back under the control of the uniparty. It's a very tough choice, but I have to say Jeb is worse. People like the Bushes and Rupert Murdoch have megalomaniacal visions and still exercise significant influence over the country, whereas Caitlyn Jenner's delusion is personal and far less impactful.
Bruce is friends with Trump so that doesn't really matter to me if he endorses him. Trump still needs to talk about the LGBT agenda and grooming of kids like DeSantis has. If he doesn't that's a mark against him, more than any endorsement.
Likewise, Jeb endorsing "not Trump" doesn't surprise me.