Small nit pick: Musk didn't put up $44 billion. His commitment is about half that, with the rest coming from other investors (e.g., a16z, Sequoia, individuals) and debt issued by Twitter, Inc.
The way to think about net worth once you get past the upper-middle-class wage-laborer level is "You have assets that the market currently values at $XB, and you want to trade for other assets valued at $XB, and the true value of the assets you currently hold is $YB < $XB [otherwise you'd hold onto them], and you hope that the true value of the assets you're buying is $ZB > $XB." Under this framework, though, it's possible to come out ahead even if $ZB < $XB, as long as $ZB > $YB. It could be he bought Twitter at an inflated price, but he bought it with Tesla shares and leverage that was even more inflated, and so it still works out.