He basically pivoted the WC success into making movies (the Kojima model) and the Wing Commander movie was so bad that it killed both the franchise and his career in film. He still had money so got to be a producer on a few flicks, but never had any creative control again.
And Freelancer was so horribly mismanaged that it basically “blacklisted” him as far as game dev went.
Star Citizen was basically an attempt to take advantage of the crowd funding craze that somehow also keyed in on what is largely the rise of “influencer” games where people care more about the dream of doing something than actually doing it (Dwarf Fortress and EVE Online are earlier examples where the vast majority of fans will never play the game but might buy it to “try it”).
Speculation, but I assume the attempts to make a bunch of tech that does what everyone else already does but poorly is trying to build out a portfolio for a buyout.
And it is worth understanding that Wing Commander… very much benefited from being “first” and for having a few celebrities involved. Even by WC4 there were “third party” games like Star Crusader that were basically better in every possible way. And Star Wars had been doing x-wing games since '93.
And then Freespace hit in 98 and was a revelation (with Freespace 2 in '99 basically being the gold standard to this day).
In a lot of ways, Squadron 42 was so anticipated mostly because we hadn’t had anything in the genre for years by that point (Darkstar One sort of existed?). Sort of like how almost all the xcom sickos played UFO ET and found it “fine” and a lot of the JA2 sickos played 5.56 and… anyway. Or us Silent Storm fans who tried to tolerate Hummer & Sickle.