Otherwise, it probably would have crept into 1996.
Depending on how you slice it, Windows 95 wasn't really baked until Windows 98 SE, so call it '99 to get out of beta testing. All things considered, for a GUI shell on DOS that version was as good as it got.
Despite how Gates got the money, he's still giving it away. I don't see Jobs giving away the billions that he has. And of course he doesn't have to, but there's a reason many people see Jobs as arrogant.
Jobs is just hording his money until he an buy the world. Or at least do a hostile take-over of Microsoft via the combined Disney/Apple empire.