Here is the brunt of why they think the deal won't go through: because it is difficult to prove extent of damages and because innocent third parties (the banks partnering with Musk) would be adversely affected, the courts will be disinclined to trigger the historically rare 'specific performance' to compel the merger. They believe a more likely outcome is Musk will instead be compelled to pay the $1 billion but a decade-long legal battle will ensue over it.
While it is an interesting listen, I wish they provided more substance for their conclusions especially since they're running counter to most other debate I'm seeing. Third parties aside, I fail to understand how legally the courts cannot pursue Musk's personal assets for the full amount. But I'm not a lawyer and haven't read the purchase agreement in detail.
Since it would take forever, it's much more likely the two sides settle or give up before they run out of legal tricks.
July 4th: https://openargs.com/oa610-elons-twitter-deal-was-a-complete...
May 12: https://openargs.com/oa595-shareholders-sue-twitter-alleged-...