Yup, and the whole point of doing it right now is that it gives him the most leverage. No one wants to stop the merger and the longer you wait, the more risky it gets (buyer's remorse, another startup comes up with a competing product, etc.) so you might be willing to pay a small but substantial sum to make the problem go away.
Given he didn't take the offer of a sum to make it go away and instead let it drag longer in a way which affects the merger, either that wasn't his logic, or he executed it poorly.
Or they lowballed him. Its hard to make assumptions here without the full story.
Fair point, but from the way Sam wrote it up it sounds like he ignored them and let it get far enough that they filed a suit against him, whereas if his plan was to be something they can get rid of quickly before the merger he surely would have come to the negotiating table before it became too late.