If Uber was in any real jeopardy of being found liable here they would have settled for far more. We know this because if Uber lost the case outright they would face an injunction against their self-driving business that would probably force them to license Waymo tech or put an end to the whole endeavor. Uber ATG is worth a lot more than what they paid in equity, and this is not an amount that matters at all to Google. The dollar figure is just there so Google can say they didn't come away with nothing.
The settlement wasn't just for money, it also barred Uber from use of some of the disputed trade secrets/technology, which could be valuable for Google. Given that Uber hasn't monetized the technology yet, it would be hard to prove any damages. The outcome of a trial could have been a similar amount and an injunction and still been a big win for Google if the future self driving market is really going to be big and if the covered technology really was crucial.
What did they get? Unjust Enrichment sized damages and mutually agreed forbearance equivalent to injunctive relief.
And that's before we get into discussing how much of a minefield discovery was becoming in the case.
2) Because prior to the trial there would have been a flurry of discovery related motions, a large amount of time pulling engineers off their jobs to have them perform witness prep at both companies, then a large period of pre-trial legal prep, then the trial itself.
At all stages, information is leaking, and expenses are going up.
... And then the appeals start.
... Then the partial re-trials and appeals on those.
Settlement is the most common way civil litigation disputes are resolved. Trials are the anomaly.
In this case, both parties likely recognized that getting into a knife fight about documentary production in a high-stakes race-to-market matter was likely in Cruise's favor, not theirs.
You don't toss someone a few hundred million dollars because your case is 'flimsy', and 'winning or losing' in court is too simplistic an analysis of the impact of the lawsuit on both sides as well as their third party competitors.
The Jeong article reads like someone read Uber's submissions to the court, phrased them in common vernacular, then ignored everything that didn't fit their narrative.