Both Jobs and Gates tried to snare him with the same fallacy. It was easy for him to do because he was very good/had insider knowledge so he shouldn't be paid that much for it. Wrong.
What really mattered was how much it was worth to Microsoft or Apple and especially that it was worth a good bit to both. Picture Scotty asking if that's worth somthin' t'ye or shd'aye just punch up clear?
It's a tough one, though. It sounds like an important thing to Andy was getting more of his work onto a bunch of Macs, where it could make the most impact. Which meant getting it bundled. Which meant making Steve happy.
Imagine Andy's horror, for example, if Steve had someone else build the Apple-blessed switcher instead and it worked but lacked the elegance and care of the Hertzfeld version.
Steve ended up having something Andy wanted, too. I gotta believe Jobs is a tough enough negotiator under the best of circumstances. Imagine when he's got you by your idealism.
The only possible leverage he could have had would have been to try to get Gates and Jobs into a bidding war. But that only works if Microsoft sees it as a competitive advantage to have the switcher for their apps but no one else's.
And, like you said, Andy already admitted he wanted it on all Macs, which blew any chance at leverage he had.
It's hard to say, because we weren't there. But I would have just said, then and there, "bullshit, I'll talk to Bill" and walked out the office - 10$ says he wouldn't have made it to the exit :)
Times were different back then. The market was nothing whatsoever like it is today. The context of this was for applications microsoft was writing for the mac, not for operating system development... and the fact that he had insider knowledge could have been used against him. And $100,000 was a decent amount of money at the time.
Are you sure you're not quoting a Simpsons episode? If I'm not mistaken, he followed that quote with instructions to his thugs to "buy 'em out, boys.", whereby they proceeded to trash the office of the dot-com in question.
I feel like, as time progresses linearly and The Simpsons continues to air new episodes, the probability that a given quote perceived to be from history is actually from a Simpsons episode asymptotically approaches 1.
What really mattered was how much it was worth to Microsoft or Apple and especially that it was worth a good bit to both. Picture Scotty asking if that's worth somthin' t'ye or shd'aye just punch up clear?