Apple saw Microsoft doing wrong and enforced its legal rights. Apple settled allowing Microsoft to save face under the threat of losing Office. It would have been a pyrrhic victory to win the suit and then lose more than the judgment because of the loss of Office.
deals only happen when both sides think it’s a win for them
Or when one side has the other over a barrel. Apple had the upper hand in the suit, but Microsoft had the trump card in the larger picture.
MS was losing plenty of suits around that time, only tech watchers really seemed to care, even MS didn’t seem to care much. I don’t think getting nailed for stealing some code was a loss of face issue for MS. Keep in mind too it had been a while since MS had updated Mac Office, they basically skipped porting 95 to Mac, and given their relationship it’s actually note worthy that they were even working on new Mac version at all.
I don’t really think anybody was over the barrel. MS could afford to lose another suit, while Apple would have been uncomfortable having no major productivity software for the Mac the would have survived. I think getting into the suit was the culmination of years of bad blood and somewhere during negotiations it dawned on them that bad blood makes for bad decisions, so they came to an agreement, added a “punishment” that did nothing (forcing MS to buy dividend paying stock which they then sold at a profit, very Br’er Rabbit as punishments go), and really up until the recent Mac ads have been pretty friendly to each other.
That's why it went to a negotiated settlement where such issues could be addressed. In a court suit, the jury could have only awarded past and future royalties and treble damages for the willful nature of the act... but there is no give and take reflecting other issues that were as important or more so.
In any case, the purchase of the $150,000,000 dollars of preferred stock that was restricted (MS could not convert, sell the stock, or even borrow money against it without Apple's explicit permission) could be better looked at as a surety bond... money that Apple could have kept locked up for years had Microsoft reneged on any of the agreements. It was not a "Cash infusion" to bail out a competitor. It was a hostage.